Tag: M.W=100-200

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 4333-56-6, name is Bromocyclopropane, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C3H5Br

To a cooled (0 C) solution of potassium tert butoxide (0.36 g, 2.9 mmol) in DMSO (12 mL) was added 3-bromothiophenol (0.50 g, 2.6 mmol) under a nitrogen atmosphere and the reaction mixture was stirred for 15 min. A solution of cyclopropylbromide (0.96 g, 7.8 mmol) in DMSO (1.0 mL) was added dropwise. The reaction mixture was allowed to warm to rt, and followed by heating to 80 C for 48 hrs. The reaction mixture was cooled to rt and diluted with cold water (10 mL) and EtOAc (10 mL). The layers were separated and the aqueous layer was extracted EtOAc (20 mL x 2). The combined organic extracts were washed with water, brine, dried over Na2S04 and concentrated in vacuo to give the title compound (0.40 g, 66% yield). MS (ESI) 230.1 [M+H]+..

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 4333-56-6.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; EXELIXIS PATENT COMPANY LLC; KICK, Ellen, K.; BODAS, Mandar; MOHAN, Raju; VALENTE, Meriah; WURTZ, Nicholas; PATIL, Sharanabasappa; WO2014/144037; (2014); 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. 630-17-1, name is 1-Bromo-2,2-dimethylpropane, A new synthetic method of this compound is introduced below., Recommanded Product: 1-Bromo-2,2-dimethylpropane

F) ethyl 3-cyclopropyl-3-(6-((6-(2-fluoro-5-methoxyphenyl)-5-(neopentyloxy)pyridin-3-yl)methoxy)pyrimidin-4-yl)propanoate Under a nitrogen atmosphere, to a solution of ethyl 3-cyclopropyl-3-(6-((6-(2-fluoro-5-methoxyphenyl)-5-hydroxypyridin-3-yl)methoxy)pyrimidin-4-yl)propanoate (60 mg) in DMF (1.3 mL) were added 1-bromo-2,2-dimethylpropane (80 muL) and cesium carbonate (83 mg), and the mixture was stirred at 80C for 20 hr. The reaction mixture was poured into water at room temperature, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (20 mg) as a colorless transparent amorphous solid. 1H NMR (300 MHz, CDCl3) delta 0.13-0.37 (2H, m), 0.43-0.56 (1H, m), 0.56-0.73 (1H, m), 0.91 (9H, s), 1.02-1.16 (1H, m), 1.16-1.24 (3H, m), 2.30-2.42 (1H, m), 2.79 (1H, dd, J = 15.6, 5.8 Hz), 3.04 (1H, dd, J = 15.6, 8.9 Hz), 3.64 (2H, s), 3.77-3.86 (3H, m), 3.99-4.16 (2H, m), 5.47 (2H, s), 6.75 (1H, s), 6.85-6.95 (1H, m), 6.96-7.05 (2H, m), 7.35 (1H, s), 8.37 (1H, s), 8.75 (1H, s).

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; Takeda Pharmaceutical Company Limited; MIWATASHI, Seiji; SUZUKI, Hideo; OKAWA, Tomohiro; MIYAMOTO, Yasufumi; YAMASAKI, Takeshi; HITOMI, Yuko; HIRATA, Yasuhiro; EP2816032; (2014); 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. 4117-09-3, name is 7-Bromo-1-heptene, A new synthetic method of this compound is introduced below., Product Details of 4117-09-3

Mg shavings (939 mg, 38.6 mmol) are suspended in Et2O (20 ml)and 1-bromohept-6-ene (3.385 g, 19.115 mmol) is added dropwise. Thereaction mixture is stirred at RT for 3 h. Then the Grignard reagent isadded to EtOSiCl3 (945 mg, 5.150 mmol), dissolved in Et2O (20 ml), at 0 C via cannula. The reaction mixture is allowed to warm to RT andthen stirred for 2 h. Subsequently, 20 ml of the solvent are removed invacuo and 20 ml of hexanes are added to precipitate the salts formedduring the Grignard reaction. The reaction mixture is ffiltered throughcelite and the solvent removed in vacuo. The crude product is purifiedby column chromatography (SiO2, hexanes : ethylacetate=8 : 1) and 2 from the first fraction. The colorless liquid 2d (510 mg, 0.778 mmol) isisolated from the second fraction as the major product in 30% yield. Tris(hept-6-enyl)ethoxysilane 21H NMR (CDCl3, 499.7 MHz): X (ppm)=5.81 (ddt,3Jtrans(1H-1H)=16.9, 3 Hz, 3Jcis(1H-1H) =10.2 Hz, 3J(1H-1H) =6.7 Hz,3H, H6), 4.99 (ddt, 3Jtrans(1H-1H) =17.1 Hz, 2J(1H-1H) =2.1 Hz, 4J(1H-1H) =1.5 Hz, 3H, H7Z), 4.93 (ddt, 3Jcis(1H-1H) =10.2 Hz, 2J(1H-1H) =2.3 Hz, 4J(1H-1H) =1.1 Hz, 3H, H7E), 3.65 (q, 3J(1H-1H)=6.9 Hz, 2H, H8), 2.00-2.07 (m, 6H, H5), 1.30-1.41 (m, 18H, overlappingH2, H3, H4), 1.17 (t, 3J(1H-1H) =6.9 Hz, 2H, H9), 0.56-0.61(m, 6H, H1); 13C{1H} NMR (CDCl3, 125.7 MHz): X (ppm)=139.21(C6), 114.11 (C7), 58.37 (C8), 33.73 (C5*), 33.11 (C3*), 28.57 (C4),23.02 (C2), 18.65 (C9), 13.59 (C1), *assignments interchangeable; 29Si{1H} NMR (CDCl3, 79.4 MHz): X (ppm)=15.36 (s).Hexakis(hept-6-enyl)disiloxane 2d.1H NMR (CDCl3, 499.7 MHz): X (ppm)=5.81 (ddt, 3Jtrans(1H-1H)=16.9 Hz, 3Jcis(1H-1H) =10.2 Hz, 3J(1H-1H) =6.7 Hz, 6H, H6), 4.99(ddt, 3Jtrans(1H-1H) =17.1 Hz, 2J(1H-1H) =2.1 Hz, 4J(1H-1H) =1.5 Hz,6H, H7Z), 4.93 (ddt, 3Jcis(1H-1H) =10.2 Hz, 2J(1H-1H) =2.2 Hz, 4J(1H-1H) =1.2 Hz, 6H, H7E), 2.04 (dt, 3J(1H-1H) =6.7 Hz, 3J(1H-1H)=6.6 Hz, 12H, H5), 1.30-1.43 (m, 36H, overlapping H2, H3, H4), 0.56-0.61 (m, 12H, H1); 13C{1H} NMR (CDCl3, 125.7 MHz): X(ppm)=139.16 (C6), 114.15 (C7), 33.69 (C5*), 33.01 (C3*), 28.57(C4), 22.91 (C2), 14.99 (C1), *assignments interchangeable

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:
Article; Guenther; Reibenspies; Bluemel; Molecular catalysis; vol. 479; (2019);,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 59907-13-0, name is 2-Bromo-1-fluoro-3-methylbenzene, belongs to bromides-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 59907-13-0, Computed Properties of C7H6BrF

[0314] To a solution of 7-isopropyl-2-methyl-3-(4,4,5,5-tetramethyl-[l,3,2]dioxaborolan-2- yl) -pyrazolo[l,5-a]pyrimidine-5-carboxylic acid ethyl ester (120 mg, 0.32 mmol) and 2- bromo-l-fluoro-3-methyl-benzene (60.8 mg, 0.322 mmol) in toluene (3 mL) were added Pd(PPh3)4 (37.2 mg, 0.032 mmol) and K3P04 (273.4 mg, 1.28 mmmol). The resulting mixture was bubbled with N2 for 5 mins and stirred at 130 C irridiated by microwave for 2 hrs. Then the reaction mixture was filtered, and the filtrate was concentrated in vacuum to give a residue, which was purified by a reversed-phase column (B from 5-95, A: H20, B: ACN) to afford 3-(2-fluoro-6-methyl-phenyl) -7-isopropyl-2-methyl-pyrazolo[l,5- a]pyrimidine-5-carboxylic acid ethyl ester (30.0 mg, yield: 26%) as a yellow solid. [0315] 1HNMR (400 MHz, CD3OD): delta = 7.46 (s, 1H), 7.37-7.31 (m, 1H), 7.18 (d, J = 7.6 Hz, 1H), 7.04 (t, J= 8.8 Hz, 1H), 4.44-4.39 (m, 2H), 3.96-3.92 (m, 1H), 2.37 (s, 3H), 2.14 (s, 3H), 1.51 (d, J= 6.8 Hz, 6H), 1.38 (t, J= 7.2 Hz, 3H). MS: m/z 356.2 (M+H+).

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, 2-Bromo-1-fluoro-3-methylbenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SANFORD BURNHAM PREBYS MEDICAL DISCOVERY INSTITUTE; SMITH, Layton H.; PINKERTON, Anthony B.; HERSHBERGER, Paul; MALONEY, Patrick; MCANALLY, Danielle; (167 pag.)WO2019/32720; (2019); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 656-64-4,Some common heterocyclic compound, 656-64-4, name is 3-Bromo-4-fluoroaniline, molecular formula is C6H5BrFN, 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.

Step C: 4-Amino-N-(3-bromo-4-fluorophenyl)-N’-hydroxy-1,2,5-oxadiazole-3-carboximidamide (4) 4-Amino-N-hydroxy-1,2,5-oxadiazole-3-carboximidoyl chloride (33.8 g, 208 mmol) was mixed with water (300 mL). At 60 C., 3-bromo-4-fluoroaniline (Sigma-Aldrich) (43.6 g, 229 mmol, 1.1 equiv.) was added to the suspension with stirring for 10 min. A solution of sodium bicarbonate (26.3 g, 313 mmol, 1.5 equiv.) in water (300 mL) was added over 15 min with stirring at 60 C. After stirring 20 min, LCMS indicated reaction completion. The reaction mixture was then cooled to room temperature and extracted with ethyl acetate (2*300 mL). The combined ethyl acetate solution was dried over anhydrous sodium sulfate and concentrated to give the desired product (65 g, 99%) as an off-white solid, which was used in the subsequent reaction without further purification. C9H7BrFN5O2 (MW 316.09), LCMS (EI) m/e 316/318 (M++H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Bromo-4-fluoroaniline, its application will become more common.

Reference:
Patent; INCYTE CORPORATION; Tao, Ming; Frietze, William; Meloni, David J.; Weng, Lingkai; Zhou, Jiacheng; Pan, Yongchun; US2015/133674; (2015); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 10269-01-9, name is (3-Bromophenyl)methanamine, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 10269-01-9

General procedure: A mixture of 0.55mmol of 8-bromo-7-(2-bromoethyl)theophylline 7a or 8-bromo-7-(3-chloropropyl)theophylline 7b or 8-bromo-7-(4-bromobutyl)theophylline 7c, 1.1mmol of appropriate aromatic amine, 1,6 mmol of TEBA and 1.00ml of propanol was heated in closed vessels in microwave oven (300 Watt, Power Max Off, 160C, 10bar) for 1h. The solvent was removed and the residue was treated with ethanol. The products were purified by crystallization from ethanol or flash column chromatography over silica gel with CH2Cl2 : MeOH (100 : 0 to 80 : 20). The precipitate was filtered off and dried.

According to the analysis of related databases, 10269-01-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Za?uski, Micha?; Schabikowski, Jakub; Schlenk, Miriam; Olejarz-Maciej, Agnieszka; Kubas, Bart?omiej; Karcz, Tadeusz; Kuder, Kamil; Latacz, Gniewomir; Zygmunt, Ma?gorzata; Synak, David; Hinz, Sonja; Mueller, Christa E.; Kie?-Kononowicz, Katarzyna; Bioorganic and Medicinal Chemistry; vol. 27; 7; (2019); p. 1195 – 1210;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 16657-07-1,Some common heterocyclic compound, 16657-07-1, name is 7-Bromo-1H-indene, molecular formula is C9H7Br, 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.

(1) Synthesis of 7-isopropylindene Using a 300 ml three-necked flask as the reactor, under a nitrogen stream, 1.36 g (2.57 millimoles) of [1,2-bis (diphenylphosphino)ethane]dichloronickel(II) was dissolved in 20 ml of tetrahydrofuran. To this suspension there was added a solution of 10 g (51.30 millimoles) of 7-bromoindene in 100 ml of tetrahydrofuran, prepared based on the method described in J. Org. Chem. 49, 4226-4237(1984). After dropwise addition of 51 ml (102.60 millimoles) of isopropylmagnesium bromide (2N) to the mixed solution while cooling on ice, the mixture was heated to reflux for 20 hours. After reflux, hydrolysis was performed with a saturated aqueous solution of ammonium chloride, distilled water was added, extraction was performed several times with diethyl ether, and then the extract was washed once with saturated saline and dried over anhydrous magnesium sulfate. After drying, the magnesium sulfate was filtered off and the solvent was purified with a silica gel column to obtain 7.14 g of 7-isopropylindene as a yellow oil (88% yield).

The synthetic route of 16657-07-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chisso Petrochemical Corporation; US2003/149200; (2003); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 51376-06-8, name is 5-Bromobenzo[c][1,2,5]oxadiazole, This compound has unique chemical properties. The synthetic route is as follows., Formula: C6H3BrN2O

5-Brorno-2,l,3-benzoxadiazole (5.5 g, 27.6 mmol)), potassium vinylfluoroborate (7.40 g, 55.3 mmol), and PdC12(dppi>;CH2C12Adduct (1.088 g, 1.332 mmol) were suspended in ethanol (75 ml) then added TEA (7.70 ml, 55.3 mmol). The reaction mixture was then degassed and heated to reflux for 3hrs. The reaction was diluted with ethyl acetate and washed with brine. The organic layer was dried over Na2SO4, filtered and evaporated to dryness. The residue was purified through a 330g ISCO Redi-Sep silica gel plug and eluted with 20%ETOAc/hexane to yield 5- ethenyl-2 , 1 , 3 -benzoxadiazole.1H-NMR (600 MHz5 CDCl3): delta ppm 7.81(d, J=9.3 Hz, IH), 7.66 (s, IH), 7.63 (d, J-9.3 Hz, IHX 6.35 (d, J=10.9 Hz, 0.5H), 6.80 (d, J-10.9 Hz, 0.5H)s 5.94 (d. J-17.5 Hz, IH)5 5.55 (d, J= H Hz5 IH).

According to the analysis of related databases, 51376-06-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP &; DOHME CORP.; PASTERNAK, Alexander; SHAHRIPOUR, Aurash; TANG, Haifeng; TEUMELSAN, Nardos, H.; YANG, Lihu; ZHU, Yuping; WALSH, Shawn, P.; WO2010/129379; (2010); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 38573-88-5, name is 1-Bromo-2,3-difluorobenzene, belongs to bromides-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 38573-88-5, Computed Properties of C6H3BrF2

EXAMPLE 93 (R,S)-3-[4-(2,3-difluorophenyl)piperazin-1-yl]-2-[(R,S)-(2-methoxyphenyl)(1-naphthyl)methyl]-2-methyl-3-oxopropanenitrile (RR,SS)-3-(2-methoxyphenyl)-2-methyl-3-(1-naphthyl)-2-(piperazin-1-ylcarbonyl)propanenitrile (471 mg, 1.14 mmol), 2,3-difluorobromobenzene (200 mg, 1.04 mmol), sodium tert-butoxide (139 mg, 1.45 mmol), tris(dibenzylideneacetone)dipalladium (0) (28 mg, 0.031 mmol), racemic BINAP (39 mg, 0.062 mmol), and toluene (3 mL) were combined in a Carius tube, vacuum degassed, placed under an argon atmosphere, sealed and heated to 80¡ã C. overnight. The reaction was cooled, taken up in diethyl ether, filtered, washed with water, saturated aqueous sodium bicarbonate, brine, dried over MgSO4, filtered, evaporated, and purified on slica gel (10percent hexanes/CH2Cl2) to yield 280 mg of the title compound as an off-white crystal solid. mp 198-200¡ã C.; 1H NMR 500 MHz (DMSO-D6): delta 7.98 (d, 1H, J=7.33 Hz), 7.86 (m, 2H), 7.79 (d, 1H, J=8.25 Hz), 7.54 (t, 1H, J=7.64 Hz), 7.42 (m, 2H), 7.23 (t, 1H, J=7.64 Hz), 7.12 (m, 2H), 7.08 (m, 1H), 7.00 (q, 1H, J=9.01 Hz), 6.79 (m, 2H), 6.01 (s, 1H), 4.01 (s, 3H), 3.73 (bs, 4H), 2.96 (bs, 4H), 1.64 (s, 3H) MS (ESI) m/z 526 ([M+H]+); Anal. calcd for C32H29F2N3O2.0.20H2O: C, 72.63; H, 5.60; N, 7.94. Found: C, 72.65; H, 5.58; N, 7.79.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; Wyeth; US2005/256132; (2005); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 65896-11-9, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 65896-11-9, name is 2-Bromo-6-fluoroaniline, This compound has unique chemical properties. The synthetic route is as follows.

A mixture of 5,8-dimethoxy-1,2,3,4-tetrahydro-1,4-methanonaphthalene-6-carbaldehyde 1 (0.23g, 0.97mmol), 2-bromo-6-fluoroaniline 9c (1 equiv, 0.18g, 0.97mmol), NaCNBH3 (2.5 equiv, 0.15g, 2.4mmol) and acetic acid (2 equiv, 0.12g, 1.9mmol) in iso-propanol (20mL) was stirred at room temperature for seven days. After this time, a saturated aqueous solution of Na2CO3 (15mL) was added and an extraction with EtOAc was performed (3¡Á15mL). After drying of the combined organic phases (MgSO4), filtration and evaporation, crude aniline 10c was obtained, which was purified by reverse phase automated flash chromatography (0.080g, 0.19mmol). 2-Bromo-N-[(5,8-dimethoxy-1,2,3,4-tetrahydro-1,4-methanonaphthalen-6-yl)methyl]-6-fluoroaniline 10c. Pale yellow oil. Gradient used for purification: during 3 CV: 40% CH3CN, during 30 CV: 40 -> 100% CH3CN, during 3 CV: 100% CH3CN. Yield 20%. 1H NMR (400MHz, CDCl3): delta 1.17-1.28 (2H, m), 1.48 (1H, ddd, J=8.7Hz, 1.4Hz, 1.4Hz), 1.69-1.72 (1H, m), 1.86-1.98 (2H, m), 3.55-3.57 (1H, m), 3.62-3.64 (1H, m), 3.76 (3H, s), 3.86 (3H, s), 4.38 (1H, br s), 4.47 (2H, d, J=4.4Hz), 6.61 (1H, ddd, J=8.2Hz, 8.1Hz, JH,F=4.9Hz), 6.95 (1H, ddd, JH,F=12.4Hz, J=8.2Hz, 1.4Hz), 7.22 (1H, ddd, J=8.1Hz, 1.4Hz, 1.3Hz). 13C NMR (100.6MHz, ref=CDCl3): delta 26.6, 27.1, 39.7, 41.5, 46.7 (d, J=9.6Hz), 49.1, 56.0, 61.5, 110.2, 113.9 (d, J=5.5Hz), 116.0 (d, J=21.3Hz), 119.6 (d, J=8.5Hz), 128.2 (d, J=3.1Hz), 129.5, 135.4 (d, J=12.0Hz), 136.5, 140.3, 146.3, 148.9, 153.4 (d, J=245.0Hz). 19F NMR (376.5MHz, CDCl3, ref=CFCl3): delta-124.10 (1F, dd, JH,F=12.4Hz, 4.9Hz). MS (ES+): m/z (%): 217 (100).

The chemical industry reduces the impact on the environment during synthesis 2-Bromo-6-fluoroaniline. I believe this compound will play a more active role in future production and life.

Reference:
Article; Cappoen, Davie; Torfs, Eveline; Meiresonne, Tamara; Claes, Pieter; Semina, Elena; Holvoet, Francis; de Macedo, Maira Bidart; Cools, Freya; Piller, Tatiana; Matheeussen, An; Van Calster, Kevin; Caljon, Guy; Delputte, Peter; Maes, Louis; Neyrolles, Olivier; De Kimpe, Norbert; Mangelinckx, Sven; Cos, Paul; European Journal of Medicinal Chemistry; vol. 181; (2019);,
Bromide – Wikipedia,
bromide – Wiktionary