Tag: M.W=100-200

Synthetic Route of 5469-19-2, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 5469-19-2 name is 1-Bromo-2,4,5-trimethylbenzene, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

i 2,4,5-Trimethylbenzoic acid n-Butyllithium (100 ml of a 2.5M solution in hexanes) was added to a solution of 5-bromo-1,2,4-trimethylbenzene (50 g) in tetrahydrofuran (600 ml) at -70 C. After 1.5 hours the solution was warmed to -40 C. then cooled to -70 C. Carbon dioxide gas was bubbled through the solution for 10 minutes and the mixture was allowed to warm to room temperature. The solvent was evaporated and the residue partitioned between water and isohexane. The aqeous layer was acidified to pH 1 and extracted with dichloromethane. The organic solution was dried (MgSO4) and evaporated under reduced pressure. Yield 36.7 g. 1H NMR: delta (CDCl3) 7.85(s, 1H), 7.04(s, 1H), 2.59(s, 3H), 2.28(s, 3H), 2.27(s, 3H)

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Bromo-2,4,5-trimethylbenzene, and friends who are interested can also refer to it.

Reference:
Patent; AstraZeneca U.K. Limited; US6162808; (2000); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 7745-91-7, These common heterocyclic compound, 7745-91-7, name is 3-Bromo-4-methylaniline, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

[00236] A suspension of 3 -bromo-4-methylaniline (184 mg, 1.0 mmol), 2-(tributylstannyl)- 1,3-oxazole (430 mg, 1.2 mmol), CuO (8 mg, 0.1 mmol) and Pd(PPli3)4 (1 15 mg, 0.1 mmol) in dioxane (2 mL) was stirred at 100 C for 3 hours under argon atmosphere on microwave synthesizer. The crude product was purified by prep-HPLC (MeCN/10 mM NH4HCO3) to give 4-methyl-3-(l,3-oxazol-2-yl)aniline (92 mg, 52%) as an oil. ES-MS m/z: 175.2 [M + H]+. LC- MS Purity (254 nm): > 99%; tR= 1.31 min.

The synthetic route of 7745-91-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LYSOSOMAL THERAPEUTICS INC.; SKERLJ, Renato, T.; LANSBURY, Peter, T.; GOOD, Andrew, C.; BOURQUE, Elyse Marie, Josee; (253 pag.)WO2016/73891; (2016); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 3814-30-0, name is (Bromomethyl)cyclopentane, A new synthetic method of this compound is introduced below., HPLC of Formula: C6H11Br

Step 2: To a suspension of 6-(4-fluorobenzyl)-3-(tetrahydro-2H-pyran-4-yl)- [1 ,2,4]triazolo[4,3-a]pyrazin-8(7H)-one (150 mg, 456.84 micromol) in anhydrous DMF (5 ml_) was added (bromomethyl)cyclopentane (89. mg, 548.21 micromol) and K2CO3 (95 mg, 685.27 micromol). The mixture was heated at 60C for 12 h. LCMS showed 23% TM. The mixture was concentrated and the residue was dissolved in DCM (20 ml_) and H2O (20 ml_). The aqueous layer was extracted with DCM (20 ml_). The combined organics were washed with H2O (20 ml_), dried over Na2SO4, filtered, concentrated and purified by prep-TLC (DCM/MeOH=50/1 ) to give 7- (cyclopentylmethyl)-6-(4-fluorobenzyl)-3-(tetrahydro-2H-pyran-4-yl)- [1 ,2,4]triazolo[4,3-a]pyrazin-8(7H)-one (25.90 mg, 13.67% yield) . 1H NMR (CDCI3 400MHz): 5 7.17-7.13 (m, 2H), 7.1 1 -7.06 (m, 2H), 6.64 (s, 1 H), 4.13-4.10 (m, 2H), 3.94 (s, 2H), 3.90 (d, J=7.2 Hz, 2H), 3.59-3.53 (m, 2H), 3.13-3.12 (m, 1 H), 2.28-2.10 (m, 1 H), 2.19-2.16 (m, 2H), 1 .94-1 .91 (m, 2H), 1 .71 -1 .68 (m, 4H), 1 .54-1 .45 (m, 2H), 1 .33-1 .28 (m, 2H). LC-MS: tR = 2.84 min (METHOD 3), m/z = 41 1 .2 [M + H]+

The synthetic route of 3814-30-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; H. LUNDBECK A/S; KEHLER, Jan; RASMUSSEN, Lars, Kyhn; JESSING, Mikkel; (126 pag.)WO2016/55618; (2016); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

1003-98-1, name is 2-Bromo-4-fluoroaniline, belongs to bromides-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Application In Synthesis of 2-Bromo-4-fluoroaniline

Example 25Synthesis of 2-Bromo-4-Fluoro-5-Nitroaniline2-Bromo-4-fluoroaniline (47.5 g, 250 mmol) was added to a solution of concentrated H2SO4 (300 mL) keeping the internal temperature below 30 C. The mixture was aged for ca. 30-60 minutes then cooled to -20 C. 90% HNO3 (35 g) was added dropwise over ca. 60 minutes keeping the internal temperature between -15 to -20 C. TLC indicated a slight amount of starting material, so a further aliquot of 90% HNO3 (3 g) was added over 5 minutes at -15 to -20 C. The cold mixture was then poured on to ice H2O (ca. 1 L ice+500 mL H2O) and EtOAc (1 L). The aqueous and organic layers were partitioned and the organic layer was washed with saturated NaHCO3 (2×500 mL), dried (Na2SO4), filtered and the solvent removed under vacuum to leave a dark solid (35 g, 60%).1H NMR (DMSO-d6, 300 MHz): delta 8.27 (br. S, 2H), 7.70 (d 1H), 7.47 (d, 1H); m/z=275.9 (M+MeCN+H)+ for 79Br.

The synthetic route of 1003-98-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Singh, Rajinder; Tso, Kin; Zhang, Jing; Duncton, Matthew; Alvarez, Salvador; Kolluri, Rao; Ramphal, John; Holland, Sacha; US2011/130415; (2011); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

These common heterocyclic compound, 452-74-4, name is 1-Bromo-2-fluoro-4-methylbenzene, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. category: bromides-buliding-blocks

EXAMPLE 6 Method F Methyl 4′-[({3-[(cyanoacetyl)amino]-4-methylpyridin-2-yl}amino)methyl]-2′,3-difluoro-1,1′-biphenyl-2-carboxylate [0212] [CHEMMOL-00020] [0213] To a stirred solution of 1-bromo-2-fluoro-4-methylbenzene (0.945 g, 5 mmol) in DMF (10 mL) in a sealed tube, bis(pinacolato)diboron (2.29 g, 9 mmol), dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium (II) dichloromethane adduct (0.146 g, 0.2 mmol), and potassium acetate (1.47 g, 15 mmol) were added at room temperature. The resulting mixture was heated at 80 C. for 16 hours to provide 2-(2-fluoro-4-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, and the solution was cooled to room temperature for the next step without any workup. [0214] To the above solution, methyl 2-fluoro-6-iodobenzoate (1.40 g, 5 mmol), dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium (II) dichloromethane adduct (0.10 g, 0.15 mmol), and sodium carbonate solution (2 M, 12.5 mL, 25 mmol) were added. The resulting mixture was heated at 80 C. for 16 hours. After cooling to room temperature, the mixture was partitioned between water and diethyl ether. The organic extract was washed with brine, dried over MgSO4, filtered and concentrated under vacuum. The residue was subjected to silica gel chromatography eluted with 10% ethyl acetate in hexanes to provide methyl 2′,3-difluoro-4′-methyl-1,1′-biphenyl-2-carboxylate as a yellow oil with a mass ion of ion (ES+) of 263.0 for M+H+. [0215] A mixture of the carboxylate (0.90 g, 3.43 mmol), N-bromo-succinimide (0.672 g, 3.78 mmol), and 2,2′-azobisisobutyronitrile (0.0169, 0.10 mmol) was suspended in 50 mL carbon tetrachloride, and heated to reflux for 5 hours. The reaction mixture was filtered to remove the residue. The resulting filtrate was concentrated under vacuum, and then partitioned between ethyl acetate and water. The organic extract was washed with brine, dried over MgSO4, filtered and concentrated under vacuum. The residue was subjected to silica gel chromatography eluted with 10% ethyl acetate in hexanes to afford methyl 4′-(bromomethyl)-2′,3-difluoro-1,1′-biphenyl-2-carboxylate as a brown oil with a mass ion of ion (ES+) of 341 for M+H+. [0216] To a stirred solution of 2-amino-4-methyl-3-nitropyridine (0.306 g, 2 mmol) in DMF (2 mL) at 0 C., sodium hydride (60% dispersion in mineral oil, 0.040 g, 1 mmol) was added, and stirred at 0 C. for 20 minutes. To the resulting mixture, methyl 4′-(bromomethyl)-2′,3-difluoro-1,1′-biphenyl-2-carboxylate (0.341 g, 1 mmol) was added, and stirring continued at 0 C. for another 30 minutes. The reaction was quenched by the addition of saturated ammonium chloride (5 mL), and partitioned between ethyl acetate and water. The organic extract was washed with brine, dried over MgSO4, filtered and concentrated under vacuum. The residue was subjected to column chromatography on silica gel eluted with 20% ethyl acetate in hexanes to provide methyl 2′,3-difluoro-4′-{[(4-methyl-3-nitropyridin-2-yl)amino]-methyl}-1,1′-biphenyl-2-carboxylate as a yellow oil with a mass ion of ion (ES+) of 414 for M+H+. [0217] To a stirred solution of the above product (0.11 g, 0.266 mmol) in methanol (2 mL), tin(II) chloride dihydrate (0.24 g, 1.06 mmol) was added and heated in a sealed tube at 70 C. for 2 hours. The resulting solution was concentrated under vacuum. The residue was dissolved in ethyl acetate (20 mL), and 10% aq. sodium carbonate solution was added with vigorous stirring until pH=10. The white suspension was filtered through a pad of Celite, and the filtrate was partitioned between ethyl acetate and water. The organic extract was washed with brine, dried over MgSO4, filtered and concentrated under vacuum. The residue was subjected to silica gel chromatography eluted with 55% ethyl acetate in hexanes to provide methyl 4′-{[(3-amino-4-methylpyridin-2-yl)amino]methyl}-2′,3-difluoro-1,1′-biphenyl-2-carboxylate as a yellow solid. [0218] To a solution of the above carboxylate (0.038 g, 0.10 mmol) in DMF (1 mL), cyanoacetic acid (0.026 g, 0.30 mmol), 1-ethyl-(3-dimethylaminopropyl)-carbodiimide hydrochloride (0.038 g 0.20 mmol), 1-hydroxy-7-azabenzotriazole (0.0136 g, 0.10 mmol) were added, and N,N-diisopropylethylamine was added until pH=10. The resulting solution was stirred at room temperature for 20 hours, and partitioned between ethyl acetate and water. The organic extract was washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated under vacuum. The residue was subjected to silica gel chromatography eluted with 60% ethyl acetate in hexanes. The appropriate fractions were concentrated under vacuum, and the residue was dissolved in 60 mL of 50% acetonitrile in hydrochloric acid (2 mL conc. hydrochloric acid in 4 L water). Lyophilization of the resulting solution afforded the HCl salt of the title compound as a white solid that gave proton NMR spectra consistent with theory and a mass ion (ES+) of 451 for M+H+: 1H NMR (400 MHz, DMSO) 69.98 (br s, 1H), 7.81 (d, J=6.12 H…

The synthetic route of 1-Bromo-2-fluoro-4-methylbenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Kuduk, Scott D.; Bock, Mark G.; Feng, Dong-Mei; Su, Dai-Shi; Wai, Jenny Miu-Chun; US2004/44041; (2004); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 111721-75-6, A common heterocyclic compound, 111721-75-6, name is 2-Bromo-3-fluoroaniline, molecular formula is C6H5BrFN, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

To a solution of 2-bromo-3-fluoroanilinne (2.5 g, 13.2 mmol) and pyridine (1.1 mL, 13.2 mmol) in CH2Cl2 (8 mL) was added dropwise a solution of cinnamoyl chloride (2.3 g, 13.7 mmol) in CH2Cl2 (4 mL). The reaction mixture was stirred at room temperature under argon overnight, diluted with CH2Cl2 and evaporated to dryness. Purification by silica gel chromatography using EtOAc (100 mL). The solution was washed with 1 N HCl (50 mL), sat’d NaHCO3 (50 mL), brine (50 mL) and dried (NaSO4). Evaporation in vacuo afforded the title compound (4.3 g) as a white solid. 1H NMR (300 MHz, CDCl3) delta 6.60 (d, J=15.3 Hz, 1H), 6.92 (t, J=8.1 Hz, 1H), 7.26-7,42 (m, 4H), 7.58 (m, 2H), 7.80 (d, J=15.6 Hz, 2H), 8.36 (d, J=8.4 Hz, 1H)

The synthetic route of 111721-75-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Ruan, Fuqiang; (35 pag.)US2019/308963; (2019); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 39478-78-9, name is 5-Bromo-2-methylaniline, A new synthetic method of this compound is introduced below., Quality Control of 5-Bromo-2-methylaniline

N-(5-bromo-2-methylphenyl)acrylamide (1): To a solution of 5-bromo-2- methylaniline (2.0 g, 10.8 mmol) in dichloromethane (10 mL), diisopropylethylamine (4.18 g, 32.3 mmol) and acryloyl chloride (1.16 g, 12.8 mmol) were added at -78C. The resulting mixture was stirred at room temperature for 30 min. After completion of reaction, the reaction mixture was quenched with water and the aqueous solution was extracted with dichloromethane (2×40.0 mL). The organic layer was washed with water followed by brine solution. The organic layer was dried over anhydrous sodium sulfate and concentrated over reduced pressure. The residue was triturated with n-pentane to afford 1 (2.2 g, 85%) as an off white solid. 1H NMR (400 MHz, CDCls) delta 2.23 (s, 3H), 5.79-5.82 (dd, J = 1.1, 10.2 Hz, 1H), 6.23-6.30 (dd, J = 10.2, 16.8 Hz, 1H), 6.42 (dd, J = 1.1, 16.8 Hz, 1H), 6.99 (brs, 1H), 7.04 (d, J = 8.1 Hz, 1H), 7.20 (m, 1H), 8.20 (brs, 1H). MS m/z (M-H): 238.0

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; CELGENE AVILOMICS RESEARCH, INC.; ALEXANDER, Matthew David; MCDONALD, Joseph John; NI, Yike; NIU, Deqiang; PETTER, Russell C.; QIAO, Lixin; SINGH, Juswinder; WANG, Tao; ZHU, Zhendong; WO2014/149164; (2014); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 1003-98-1, A common heterocyclic compound, 1003-98-1, name is 2-Bromo-4-fluoroaniline, molecular formula is C6H5BrFN, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

General procedure: o-Bromaniline (1a, 0.2 mmol), benzoyl chloride (2a, 1.2 eq), Cu NPs (1.3 mg, 10 mol%), 1,10-phen(4.0 mg, 10 mol%), K2CO3 (2.0 equiv), and 1.5 mL of MeCN were added into a 5-mL sealed tubeunder N2. The mixture was stirred at 90 for 1 hour. Then, the reaction was stopped, and the reactionmixture was purified by flash column chromatography on silica gel (hexanes/EtOAc 15:1). Compound4a was obtained in >99 % of yield.

The synthetic route of 1003-98-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wang, Yong; Wu, Chaolong; Nie, Shoujie; Xu, Dingjian; Yu, Min; Yao, Xiaoquan; Tetrahedron Letters; vol. 56; 49; (2015); p. 6827 – 6832;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 1575-37-7,Some common heterocyclic compound, 1575-37-7, name is 4-Bromobenzene-1,2-diamine, molecular formula is C6H7BrN2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Preparation 1 5-Bromo-benzo[1,2,5]thiadiazole To 4-bromo-benzene-1,2-diamine (17 g, 91 mmol) was added thionyl chloride (200 ml). One drop of DMF was added to the reaction mixture. The reaction mixture was heated at reflux under argon at 80 C. overnight. The reaction mixture was cooled to room temperature and added portionwise to ice in a large beaker and neutralised with solid sodium bicarbonate. The mixture was partitioned between ethyl acetate and water. The ethyl acetate layer was collected and dried (MgSO4). The solvent was removed under reduced pressure. The title compound was isolated by column chromatography on silica gel eluding with 90% ethyl acetate/10% methanol. (12 g, 62%); 1H NMR (250 MHz, CDCl3) delta: 7.61 (1H, dd, J=9, 2 Hz), 7.82 (1H, d, J=9 Hz), 8.16 (1H, s).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Bromobenzene-1,2-diamine, its application will become more common.

Reference:
Patent; Gaster, Laramie Mary; Harling, John David; Heer, Jag Paul; Heightman, Thomas Daniel; Payne, Andrew Hele; US2004/152738; (2004); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 626-88-0, The chemical industry reduces the impact on the environment during synthesis 626-88-0, name is 1-Bromo-4-methylpentane, I believe this compound will play a more active role in future production and life.

[008191 Prepared using General Procedure 12: To a stirred solution of tert-butyl (8)-i – (2-(5-Qert-butyl)thiophene-2-carboxamido)-3-(4-(5-(4-hydroxyphenyl)pyrimidin-2- yl)phenyl)propanoyl)azetidine-3-carboxylate (INT-48) (300 mg, 0.479 mmol) in DMF (5mL) was added Cs-CO3 (197 mg, 0.58 mrnol) and 1-bromo-4-methylpentane (158 mg, 0.96 mmol). The reaction mixture was stirred for 18 h at 65C then diluted with aq. NaHCO3 (100 ml, saturated) and extracted with EA (2 X 100 mL). The combined organic layers were dried (Na2SO4), concentrated, and purified by column chromatography (EA/ hexane)to afford 188 mg (54%) of tert-butyl (S-1-(2-(5-(tert- butyl)thiophene-2-carboxarnido)-3-(4-(5 -(4-((4-methylpentyl) oxy)phenyl)pyrimidin-2- yl)phenyl)propanoyl)azetidine-3 -carboxylate .LCMS-ESI (m/z) calculated for C42H52N4O5S 724.96; found 725.3 [M±H] , /p. = 12.71 mm (Method 16). ?H NMR (400 MHz, CDC13) oe 8.97 (d, J = 7.5 Hz, 2H). 8.45 (d, J = 5.5 Hz, 2H), 7.55 (s, 2H). 7.49 – 7.31 (rn. 3H), 7.05 (d, J 6.6 Hz, 2H), 6.82 (s, IH), 6.68 (d, J= 28.8 Hz, 1H), 4.82 (s, 1H). 4.30 (s. 0.5H). 4.07 (rn, 5.5H), 3.56 (s, 0.5H), 3.31 – 3.09 (rn, 2H), 2.91 (s, 0.5H),1.83 (s, 2H), 1.60 (d, J= 25.3 Hz, 1H), 1.40 (s, 16H), 1.29 (s, 4H), 0.95 (s, 6H).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 1-Bromo-4-methylpentane, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; CELGENE INTERNATIONAL II SARL; BOEHM, Marcus, F.; MARTINBOROUGH, Esther; MOORJANI, Manisha; TAMIYA, Junko; HUANG, Liming; YEAGER, Adam, R.; BRAHMACHARY, Enugurthi; FOWLER, Thomas; NOVAK, Andrew; MEGHANI, Premji; KNAGGS, Michael; GLYNN, Daniel; MILLS, Mark; (851 pag.)WO2016/94729; (2016); A1;,
Bromide – Wikipedia,
bromide – Wiktionary