New downstream synthetic route of 1231930-33-8

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

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