Month: August 2021

Application of 51376-06-8, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 51376-06-8, name is 5-Bromobenzo[c][1,2,5]oxadiazole belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

l-(2-((2S,4R)-4-Fluoro-2-((2-fluoro-3-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2- yl)phenyl)carbamoyl)pyrrolidin-l-yl)-2-oxoethyl)-lH-indazole-3-carboxamide, 5- bromobenzo[c][l,2,5]oxadiazole, Pd(dppf)Cl2 and potassium carbonate were taken up in a pressure tube under argon. To this mixture, 8 mL of dioxane and 2 mL of water were added. The mixture was bubbled with argon for 5 min and the vial was stoppered and subjected to microwave irradiation at 100 C for 45 min. The volatiles were removed under reduced pressure and the residue was purified by ISCO (0-5 % MeOH in CH2CI2) to afford compound 68. 1HNMR (400 MHz, DMSO) (major rotamer) delta 2.10 – 2.20 (m, 1H), 2.57-2.63 (m, 1H), 3.89 – 4.04 (m, 1H), 4.24 (dd, J = 12.7, 21.8 Hz, 1H), 4.78 (t, J = 8.3 Hz, 1H), 5.47 (d, J= 17.2 Hz, 1H), 5.55 (d, J = 52.4 Hz, 1H), 5.67 (d, j = 17.2 Hz, 1H), 7.23-7.31 (m, 2H), 7.36 (s, 1H), 7.39 – 7.46 (m, 2H), 7.59 – 7.64 (m, 2H), 7.74 (d, J= 9.3 Hz, 1H), 7.98 (t, J= 7.8 Hz, 1H), 8.11 – 8.25 (m, 3H), 10.05 (s, 1H). 19F- MR (DMSO-de ) (major rotamer): delta -128.8, -175.9.

The synthetic route of 5-Bromobenzo[c][1,2,5]oxadiazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ACHILLION PHARMACEUTICALS, INC.; WILES, Jason, Allan; PHADKE, Avinash, S.; DESHPANDE, Milind; AGARWAL, Atul; CHEN, Dawei; GADHACHANDA, Venkat, Rao; HASHIMOTO, Akihiro; PAIS, Godwin; WANG, Qiuping; WANG, Xiangzhu; GREENLEE, William; (447 pag.)WO2017/35408; (2017); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 17247-58-4, These common heterocyclic compound, 17247-58-4, name is (Bromomethyl)cyclobutane, 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.

[0079] Step G: l-[2-(2,4-Dichloro-phenyl)-ethyl]-8-(3-methoxy-phenyl)-l,3- diaza-spiro[4.5]decane-2,4-dione 86 (0.52 g, 1.16 mmol), bromomethylcyclobutane (0.175 mL, 1.56 mmol) and potassium carbonate (0.32 g, 2.32 mmol) in dry DMSO (5.0 mL) are stirred for 3 h at 500C. The mixture is cooled to rt, diluted with water and extracted with DCM (3x). The combined extracts are washed with 1 N HCl, H2O (3x) and brine, dried over MgSO4, and concentrated to afford 3-cyclobutylmethyl-l-[2-(2,4-dichloro-phenyl)-ethyl]-8- (3-methoxy-phenyl)-l,3-diaza-spiro[4.5]decane-2,4-dione 87 (0.65 g, quant.) as a clear, thick oil: MS calcd. for C28H33Cl2N2O3 (MH-H+) 515.1, found 515.1; 1H-NMR (400 MHz, CDCl3) delta = 7.40 (d, J= 1.7 Hz, IH), 7.21 (m, 3H), 6.88 (d, J = 7.9 Hz, IH)5 6.83 (t, J= 2.2 Hz, IH)5 6.75 (dd, J= 2.2, 7.9 Hz, IH), 3.80 (s, 3H)5 3.54 (d, J= 7.4 Hz5 2H), 3.41 (t, J= 7.2 Hz5 2H), 3.13 (t, J= 7.2 Hz, 2H)5 2.71 (septet, J= 7.7 Hz, IH), 2.38 (m, 3H), 2.02 (m5 2H), 1.88 (m, 2H)5 1.77 (m, 6H)5 1.62 (m, 2H).

The synthetic route of 17247-58-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; IRM LLC; WO2007/87448; (2007); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 937046-98-5,Some common heterocyclic compound, 937046-98-5, name is 7-Bromopyrrolo[2,1-f][1,2,4]triazin-4-amine, molecular formula is C6H5BrN4, 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.

Into a 250-mL round-bottom flask purged and maintained with an inert atmosphere of argon, was placed a solution of compound 2a (3.2 g, 15.02 mmol) in THF (40 mL). n-Butyllithium (18.75 mL, 1.6 N in THF) was added dropwise at -78C, and then chloro[2-(chlorodimethylsilyl)ethyl]dimethylsilane (3.2 g, 14.87 mmol) was added at -78 C. After the resulting solution was stirred for 0.5 hours at -78 C, n- butyllithium (6.25 mL, 1.6 N in THF) was added. After the resulting mixture was stirred for 5 minutes, a solution of compound lh (3.7 g, 9.75 mmol) in THF (10 mL) was added to the mixture and the resulting solution was stirred for 2 hours at -78C. After that the reaction was quenched by the addition of 30 mL saturated aqueous solution of ammonium chloride, extracted with ethyl acetate (3×150 mL), dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was applied onto a silica gel column and eluted with ethyl acetate/petroleum ether (1 :20~1 :3) to provide 350 mg (7%) of compound 2c as an off-white solid. LC-MS: (ES, m/z): 514.0 [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 7-Bromopyrrolo[2,1-f][1,2,4]triazin-4-amine, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; GIRIJAVALLABHAN, Vinay; BOGEN, Stephane; PAN, Weidong; DANG, Qun; DAVIES, Ian; WO2014/59901; (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. 5433-01-2, name is 1-Bromo-3-isopropylbenzene, A new synthetic method of this compound is introduced below., SDS of cas: 5433-01-2

1-Bromo-3-isopropylbenzene 13 (1.5 g, 7.5 mmol, 1.0 eq.), acrolein-diethylacetal (3.57g, 23.43 mmol, 3.1 eq.), Bu4NOAc (5.0 g, 16.6 mmol, 2.2 eq.), potassium carbonate (1.56 g, 11.3 mmol, 1.5 eq.), potassium chloride (0.75 g, 7.6 mmol, 1.01 eq.) and palladium(II) acetate (50 mg, 0.22 mmol, 0.029 eq.) were suspended in DMF (32 mL) and heated for 24 h at 90C. The reaction mixture was cooled to room temperature, diluted with water (25 mL) and acidified with HCl 2M. After extraction with methyl-tert-butyl ether, the organic phase was washed with water and brine, dried over Na2SO4, filtered and concentrated. The residue was purified by chromatography on silica gel (hexane/EtOAc 19/1) to give 14 (928 mg, 71% yield).

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; Goncalves-Contal, Sylvie; Gremaud, Ludovic; Palais, Laetitia; Babel, Lucille; Alexakis, Alexandre; Synthesis; vol. 48; 19; (2016); p. 3301 – 3308;,
Bromide – Wikipedia,
bromide – Wiktionary

Some common heterocyclic compound, 698-19-1, name is 1-(2-Bromophenyl)-N-methylmethanamine, molecular formula is C8H10BrN, 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. Formula: C8H10BrN

To a stirred solution of commercially available1-(2-bromophenyl)-N-methylmethanamine (565 mg, 2.8 mmol, 1.0 equiv.) and propiolic acid (0.21 mL,3.4 mmol, 1.2 equiv.) in CH2Cl2 (30 mL) was added DCC (700 mg, 3.4 mmol, 1.2 equiv.) at 0 C.Then, the reaction temperature was raised to r.t. After 1.5 h, the reaction mixture was diluted withCH2Cl2 (200 mL), and then washed with aq. 2N-HCl (5 mL) and sat. aq. NaHCO3 (20 mL). The organiclayer was dried (Na2SO4), filtered, and concentrated under reduced pressure. The crude residue waspurified by column chromatography (silica gel, hexanesEtOAc 3:1) to yield 6c (675 mg, 95% yield) asan off-white solid; m.p. = 53.1 C; Rf = 0.3 (silica gel, hexanesEtOAc 2:1); IR (film) 3283, 3215, 3061,2926, 2107, 1644, 1401 cm-1; 1H-NMR (CDCl3, 1.3:1 atropisomeric mixture): delta = 7.59 (d, J = 8.0 Hz,1H, major), 7.56 (d, J = 8.0 Hz, 1H, minor), 7.35 (t, J = 7.5 Hz, 1H, major), 7.30 (t, J = 7.5 Hz, 1H, minor),7.19 (t, J = 7.8 Hz, 2H, major), 7.16 (d, J = 7.8 Hz, 2H, minor), 4.91 (s, 2H, major), 4.75 (s, 2H, minor),3.09 (s, 1H, major), 3.20 (s, 1H, minor), 2.94 (s, 3H, major), 3.18 (s, 3H, minor), ppm; 13C-NMR (CDCl3): delta= 154.4 (major), 154.2 (minor), 135.3 (major), 135.3 (minor), 133.5 (major), 133.3 (minor), 129.8 (major),129.6 (minor), 129.5 (minor), 128.4 (major), 128.3 (major), 128.2 (minor), 80.0 (minor), 79.4 (major),76.0 (minor), 75.9 (major), 54.9 (major), 50.0 (minor), 36.5 (minor), 32.7 (major) ppm; HRMS (EI): calcd. forC23H18ClNO [M+]: 250.9946, found 250.9944.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 698-19-1, its application will become more common.

Reference:
Article; Park, Sunhwa; Lee, Jiyun; Shin, Kye Jung; Oh, Euichaul; Seo, Jae Hong; Bunce, Richard A.; Molecules; vol. 22; 3; (2017);,
Bromide – Wikipedia,
bromide – Wiktionary

These common heterocyclic compound, 58971-11-2, name is 3-Bromophenethylamine, 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. Application In Synthesis of 3-Bromophenethylamine

2-(3-Bromo-phenyl)-ethylamine (0.5 mmol) and formaldehyde (0.42 mmol) were mixed in 3 ml of 1,2-dichloroethane in a process vial, which was sealed with a septum. Sodium triacetoxyborohydride (0.84 mmol) was added under argon atmosphere. The suspension was subjected to microwave irradiating conditions (CEM Discover equipped with a CEM Explorer automated reaction handling module). The reaction mixture was heated for 5 min at 90C and then cooled. The crude was evaporated to dryness and then suspended in aqueous NaHCO3. The product was extracted with CH2Cl2 and washed with aqueous NaHCO3. The CH2Cl2 extract was dried with anhydrous Na2SO4, filtered and evaporated to dryness to give the crude product [2-(3-bromo-phenyl)-ethyl]-methyl-amine. The crude was purified by flash column chromatography (CH2Cl2-MeOH as eluents) by using a CombiFlash Companion system to yield the title compound (75%) as colourless oil.

The synthetic route of 3-Bromophenethylamine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Laboratorios del Dr. Esteve S.A.; EP1935886; (2008); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 7745-91-7,Some common heterocyclic compound, 7745-91-7, name is 3-Bromo-4-methylaniline, molecular formula is C7H8BrN, 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.

C. (l,3-Dihvdw-l-hvdwxy-2,l-benzoxabowl-6-yl)-phenyl-carbamic acid t- butvl ester (59); (3-Bromo-4-methyl-phenyl)-phenyl-amine (54); [0321] To a mixture of iodobenzene (4.4 g, 21.56 mmol), 3-bromo-4- methylbenzamine (4.0 g, 21.56 mmol) and DMSO (50 mL) were added in sequence copper (I) iodide (0.82 g, 4.31 mmol), L-proline (0.99 g, 8.61 mmol) and NaOBu-t (4.14 g, 43.13 mmol) under N2. The mixture was stirred at 50 0C for 48 hbefore poured onto ice (100 g) and extracted with EtOAc (100 mL x 3). The extracts were dried over Na2SO4 and the residue after rotary evaporation was purified by column chromatography to give 1.2 g of compound 54 (21.2%). 1HNMR (300 MHz, DMSO): delta 8.19 (s, 1 H), 7.27-7.15 (m, 4 H), 7.05-7.01 (m, 2 H), 6.97 (dd, Ji = 8.4, J2 = 2.4 Hz, 1 H), 6.85 (m, 1 H) and 2.23 (s, 3 H) ppm.

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-methylaniline, its application will become more common.

Reference:
Patent; ANACOR PHARMACEUTICALS, INC.; ORR, Matthew; JENKS, Matthew; WO2011/19612; (2011); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 38573-88-5, The chemical industry reduces the impact on the environment during synthesis 38573-88-5, name is 1-Bromo-2,3-difluorobenzene, I believe this compound will play a more active role in future production and life.

Then 2,3-difluorobromobenzene (T-10) (115.2 g) was dissolved in DryTHF (600 ml), and the resultant solution was cooled to -70°C. In a nitrogen atmosphere, n-BuLi (364 ml) was added dropwise, and agitation was carried out at -70°C for 2 hours. Then, a DryTHF solution of cyclohexanedione monoethylene ketal (T-3) (93.6 g) was slowly added dropwise at -70°C, and the resultant solution was heated to room temperature and agitated for 16 hours. After completion of the reaction, 2N-HCl (200 ml) was added, extraction was carried out with toluene, an organic layer was washed with water and a saturated aqueous solution of sodium chloride, and then the resultant solution was dried over anhydrous magnesium sulfate and concentrated under reduced pressure, and thus a light brown solid was obtained. The resultant material was dissolved in toluene (400 ml), p-TsOH (4.74 g) was added, and heating reflux was carried out for 4 hours while performing dehydration. After completion of the reaction, extraction was carried out with toluene, an organic layer was washed with water and a saturated aqueous solution of sodium chloride, and then the resultant solution was dried over anhydrous magnesium sulfate and concentrated under reduced pressure, and thus a light brown solid was obtained. The resultant material was subjected to silica gel column chromatography (heptane:ethyl acetate = 20:1 in a volume ratio) and recrystallization (Solmix), and thus (T-11) was obtained as a colorless crystal (121.0 g, yield: 80percent).

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-2,3-difluorobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; JNC Corporation; JNC Petrochemical Corporation; EP2484658; (2012); 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. 25462-61-7, name is 2,5-Dibromobenzene-1,4-diamine, A new synthetic method of this compound is introduced below., name: 2,5-Dibromobenzene-1,4-diamine

Add a solution of peroxytrifluoroacetic acid in the reaction vessel, lower the temperature to -5 to 5 C, add 797.8 g (3mol) of 2,5-dibromo-p-aminoaniline, and keep the reaction at -5 to 5 C with stirring for 6 hours. After the reaction is complete, Add 2L of water, stir, and let stand. The organic layer was washed with 2L of saturated sodium bisulfite solution, 2L of saturated sodium bicarbonate solution, and water to pH 7-8. The solvent was distilled off under reduced pressure, and dichloromethane and methanol were used. The volume ratio of dichloromethane and methanol is 1: 2) The solution was recrystallized to obtain the product as a yellow solid 782.2 g of 2,5-dibromo-p-nitronitrobenzene (yield 80%).

The synthetic route of 25462-61-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chongqing Pharmaceutical College; Liu Dianqing; He Dongxian; Wang Kun; Guo Shengchao; Wang Guangming; (7 pag.)CN110330432; (2019); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 10269-01-9,Some common heterocyclic compound, 10269-01-9, name is (3-Bromophenyl)methanamine, molecular formula is C7H8BrN, 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.

1B (100 mg, 0.40 mmol),3-bromobenzylamine (74 mg, 0.40 mmol) and potassium carbonate (50 mg, 0.36 mmol)DMF was distilled off under reduced pressure. Separated with DCM-MeOH (40:1) as eluent,A white solid (41 mg, 27.9%) was obtained.

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

Reference:
Patent; Shanghai Jiao Tong University; Mao Zhenmin; Wang Yaolin; Zhan Xiaoping; (15 pag.)CN109593066; (2019); A;,
Bromide – Wikipedia,
bromide – Wiktionary