Category: 1231930-33-8

These common heterocyclic compound, 1231930-33-8, name is 6-Bromo-4-fluoro-1-isopropyl-2-methyl-1H-benzo[d]imidazole, 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. HPLC of Formula: C11H12BrFN2

3.5 g of 6-bromo-4-fluoro-1-isopropyl-2-methyl-1H-benzo[d]imidazole was dissolved in 20 ml of DMF.And add 5.1g of (BPin) 2, 0.62g of PCy3, 3.8g of KOAc and 0.3g of Pd(OAc)2, stir and heat to 100 C for 24h, stop heating and cool down to 6At 0 C, 50 ml of ethyl acetate was added, and the mixture was filtered.Add n-hexane to the oil obtained by concentration, stir and crystallize for 1 h at room temperature.Filtration gave 2.1 g of 4-fluoro-1-isopropyl-2-methyl-1H-benzo[d]imidazole-6-boronic acid pinacol ester as a pale yellow solid.

The synthetic route of 6-Bromo-4-fluoro-1-isopropyl-2-methyl-1H-benzo[d]imidazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; WISDRUG INNOCATION PHARMACY RES BEIJING CO LTD; Wentao Chuangxin Pharmaceutical (Beijing) Co., Ltd.; ZHU XIZHEN; Zhu Xizhen; DENG CHENGJUN; Deng Chengjun; ZHOU ZHONGXIANG; Zhou Zhongxiang; (17 pag.)CN107827875; (2018); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 1231930-33-8,Some common heterocyclic compound, 1231930-33-8, name is 6-Bromo-4-fluoro-1-isopropyl-2-methyl-1H-benzo[d]imidazole, molecular formula is C11H12BrFN2, 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.

6-Bromo-4-fluoro-1-isopropyl-2-methyl-1H-benzimidazole (200 mg, 0.73765 mmol) (compound represented by formula 1-a), bis(pinacolato)diboron (280 mg, 1.1 mmol), tricyclohexylphosphine (37 mg, 0.1320 mmol), potassium acetate (218 mg, 2.221 mmol) and palladium acetate (19 mg, 0.1148 mmol) were added to dimethyl sulfoxide (2 mL), and the mixture was stirred under nitrogen atmosphere at 90 C. for 2 hours. After cooling to room temperature, the reaction solution was diluted with 10 mL ethyl acetate and filtered. The filtrate was washed with saturated brine, dried over anhydrous sodium sulfate. The organic layer was concentrated and purified by silica gel column chromatography (ethyl acetate/n-hexane 0 to 50%) to give compound 4-fluoro-1-isopropyl-2-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-benzimidazole represented by formula 1-b (180 mg, 0.5657 mmol). LC-MS: m/z: (M+H)+=319.2.

The synthetic route of 1231930-33-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shanghai Pharmaceuticals Holding Co., Ltd.; XIA, Guangxin; WANG, Qian; SHI, Chen; ZHAI, Xiong; GE, Hui; LIAO, Xuemei; MAO, Yu; XIANG, Zhixiong; HAN, Yanan; HUO, Guoyong; LIU, Yanjun; (202 pag.)US2019/10153; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 1231930-33-8, These common heterocyclic compound, 1231930-33-8, name is 6-Bromo-4-fluoro-1-isopropyl-2-methyl-1H-benzo[d]imidazole, 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.

Under nitrogen protection, 24 palladium acetate (28 mg) and 25 tricyclohexylphosphine (54.3 mg) was added into the solution of 26 6-bromo-4-fluoro-1-isopropyl-2-methyl-H-benzo[d]imidazole (300 mg, 1.10 mmol), 27 bis(pinacolato)diboron (422 mg, 1.70 mmol) and 28 potassium acetate (326 mg, 3.3 mmol) in anhydrous 29 dimethyl sulfoxide (DMSO, 5 mL), and the reaction was carried out at 100 C. under nitrogen protection for 2 hours. After cooling to room temperature, the reaction was filtered on Celite, the filter cake was washed with ethyl acetate, the filtrate was washed with brine, dried over anhydrous sodium sulfate, the filtrate was concentrated under reduced pressure, and the filtrate was separated on column chromatography (eluant:petroleum ether/ethyl acetate (v/v)=3:1), to affard 260 mg of a pale yellow solid. Yield: 74.3%. LC-MS(APCI): m/z=319.3 (M+1).

The synthetic route of 1231930-33-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shenzhen TargetRx, Inc.; Wang, Yihan; Ren, Xingye; Jin, Jian; Li, Huanyin; Ai, Yixin; (162 pag.)US2019/152954; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 1231930-33-8, These common heterocyclic compound, 1231930-33-8, name is 6-Bromo-4-fluoro-1-isopropyl-2-methyl-1H-benzo[d]imidazole, 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.

DMSO (100 mL) was added to a 500 mL one-necked flask and the compound of formula XVI-1 (20.0 g,73.80 mmoL), bis (pinacolato) diboron (27.6 g, 108.69 mmol), tricyclohexylphosphine (3.53 g, 12.61 mmol)Potassium acetate (21.3 g, 217.38 mmol). Nitrogen gas was added to the reaction flask after the rapid addition of palladium acetate (1.5g), nitrogen PaulProtect the next open heating to 90C. After 3 hours the reaction flask was cooled to room temperature and the reaction mixture was poured into 700 mL of water, mixed thoroughly and subtractedPressure filtration, the filter cake was washed twice with 100mL of water and dried to give a light brown solid. Crude was added 50mL petroleum ether, 10mL BEthyl acetate beating 10min, vacuum filtration to give a white solid (18.8g, yield 80.3%)

The synthetic route of 1231930-33-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Zhengda Tianqing Pharmaceutical Group Co., Ltd.; Zhang Yinsheng; Liu Yingshuai; Qin Hui; Li Yuan; Zhao Kaidi; Miao Lei; Hu Jie; Liu Haiyan; Wang Xiaojin; (33 pag.)CN107266421; (2017); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

1231930-33-8, name is 6-Bromo-4-fluoro-1-isopropyl-2-methyl-1H-benzo[d]imidazole, belongs to imidazoles-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. name: 6-Bromo-4-fluoro-1-isopropyl-2-methyl-1H-benzo[d]imidazole

A suspension of 6-bromo-4-fluoro-2-methyl-1-(propan-2-yl)-1H-benzimidazole (Int-46) (90 g, 331.95 mmol), bis(pinacolato)diboron (126 g, 498 mmol), AcOK (80 g, 815.15 mmol), tricyclohexylphosphine (14 g, 49.8 mmol), and Pd(OAc)2 (7.45 g, 33.2 mmol) in DMSO (1.0 L) was sparged with N2 and then stirred at 100 C. for 16 h. TLC analysis (1:1 petroleum ether/EtOAc) showed complete consumption of the starting material. The black suspension was poured into H2O (3.0 L) and extracted with EtOAc (2*3 L). The combined organic phases were washed with brine, dried over Na2SO4, filtered, and concentrated. The residue was purified by flash chromatography (Biotage, 1.0 kg, 0-40% EtOAc/petroleum ether) to provide 4-fluoro-2-methyl-1-(propan-2-yl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-benzimidazole (A-1) (77 g, 73% yield) as a yellow solid. 1H NMR (400 MHz, CDCl3) delta 7.69 (s, 1H), 7.33 (d, J=10.8 Hz, 1H), 4.77-4.61 (m, 1H), 2.65 (s, 3H), 1.65 (d, J=7.0 Hz, 6H), 1.36 (s, 12H); m/z (ESI+) for (C17H24BFN2O2), 319.2 (M+H)+.

The synthetic route of 1231930-33-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Pfizer Inc.; Chen, Ping; Cho-Schultz, Sujin; Deal, Judith Gail; Gallego, Gary Michael; Jalaie, Mehran; Kania, Robert Steven; Nair, Sajiv Krishnan; Ninkovic, Sacha; Orr, Suvi Tuula Marjukka; Palmer, Cynthia Louise; (169 pag.)US2019/330196; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 1231930-33-8,Some common heterocyclic compound, 1231930-33-8, name is 6-Bromo-4-fluoro-1-isopropyl-2-methyl-1H-benzo[d]imidazole, molecular formula is C11H12BrFN2, 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.

The 6-Bromo-4-fluoro-1-isopropyl-2-methyl-1H-benzo [d] imidazole (9.0 g, 33.2 mmol)Bis-boronic acid pinacol ester(0.65 g, 49.8 mmo1), palladium acetate (840 mg), tricyclohexylphosphine (1.63 g) and potassium acetate (9,78 g, 99.8 mmo 1) were added to 60 mL of DMSO and the nitrogen was allowed to warm to 80 C for 6 h.The organic phase was extracted with EA, and the organic phase was washed with EA. The organic phase was dried with anhydrous sodium sulfate and filtered through the filtrate. The filtrate was concentrated and purified by silica gel column chromatography (PE: EpsilonAlpha = 1: 2) The title compound (6.0 g, yield 56.8%)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6-Bromo-4-fluoro-1-isopropyl-2-methyl-1H-benzo[d]imidazole, its application will become more common.

Reference:
Patent; Shandong Xuanzhu Pharmaceutical Technology Co., Ltd.; Wu, Yongqian; (45 pag.)CN104910137; (2017); B;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem