6-bromo-1-(4-methoxy-phenyl)-1H-benzo[d]imidazole → 6-[2-(4-Fluoro-phenyl)-2H-pyrazol-3-yl]-1-(4-methoxy-phenyl)-1H-benzoimidazole

HRID 2202476Notes

Reaction equation

HRID 2202476 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[CH:8][N:7]([C:10]3[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=3)[C:6]=2[CH:18]=1.[F:19][C:20]1[CH:25]=[CH:24][C:23]([N:26]2[C:30](B(O)O)=[CH:29][CH:28]=[N:27]2)=[CH:22][CH:21]=1>>[F:19][C:20]1[CH:21]=[CH:22][C:23]([N:26]2[C:30]([C:2]3[CH:3]=[CH:4][C:5]4[N:9]=[CH:8][N:7]([C:10]5[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=5)[C:6]=4[CH:18]=3)=[CH:29][CH:28]=[N:27]2)=[CH:24][CH:25]=1

Participants

3

Reactant 2

HCID 712956726-bromo-1-(4-methoxy-phenyl)-1H-benzo[d]imidazole2×HCID 900951701-(4-Fluorophenyl)-1H-pyrazol-5-ylboronic acid2×

Product 1

HCID 736718796-[2-(4-Fluoro-phenyl)-2H-pyrazol-3-yl]-1-(4-methoxy-phenyl)-1H-benzoimidazole

Procedure

The title compound, off-white solid (34 mg, 27%), MS (ISP) m/z=385.5 [(M+H)+], mp 143° C., was prepared in accordance with the general method of example 1 from 6-bromo-1-(4-methoxy-phenyl)-1H-benzo[d]imidazole (intermediate N) (100 mg, 330 μmol) and 1-(4-fluoro-phenyl)-1H-pyrazol-5-ylboronic acid (intermediate A) (81.6 mg, 396 μmol).

Sources & evidence

ORD record
ord-24abb758afd04054a57e43bf10c8e3c2
Source dataset
uspto-grants-2016_06
Patent number
US09365550B2

Reaction notes

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