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

HRID 2202471Notes

Reaction equation

HRID 2202471 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]([Cl:16])=[CH:12][CH:11]=3)[C:6]=2[CH:17]=1.[F:18][C:19]1[CH:24]=[CH:23][C:22]([N:25]2[C:29](B(O)O)=[CH:28][CH:27]=[N:26]2)=[CH:21][CH:20]=1>>[Cl:16][C:13]1[CH:14]=[CH:15][C:10]([N:7]2[C:6]3[CH:17]=[C:2]([C:29]4[N:25]([C:22]5[CH:23]=[CH:24][C:19]([F:18])=[CH:20][CH:21]=5)[N:26]=[CH:27][CH:28]=4)[CH:3]=[CH:4][C:5]=3[N:9]=[CH:8]2)=[CH:11][CH:12]=1

Participants

3

Reactant 2

HCID 900950726-bromo-1-(4-chloro-phenyl)-1H-benzo[d]imidazole2×HCID 900951701-(4-Fluorophenyl)-1H-pyrazol-5-ylboronic acid2×

Product 1

HCID 736736741-(4-Chloro-phenyl)-6-[2-(4-fluoro-phenyl)-2H-pyrazol-3-yl]-1H-benzoimidazole

Procedure

The title compound, off-white solid (44 mg, 35%), MS (ISP) m/z=389.4 [(M+H)+], mp 173° C., was prepared in accordance with the general method of example 1 from 6-bromo-1-(4-chloro-phenyl)-1H-benzo[d]imidazole (intermediate H) (100 mg, 325 μmol) and 1-(4-fluoro-phenyl)-1H-pyrazol-5-ylboronic acid (intermediate A) (80.3 mg, 390 μmol).

Sources & evidence

ORD record
ord-29428e2e45ff477ea1429868ab13de8a
Source dataset
uspto-grants-2016_06
Patent number
US09365550B2

Reaction notes

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