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

HRID 2202475Notes

Reaction equation

HRID 2202475 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][C:11]=3[F:17])[C:6]=2[CH:18]=1.[Cl: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>>[Cl:16][C:13]1[CH:14]=[CH:15][C:10]([N:7]2[C:6]3[CH:18]=[C:2]([C:30]4[N:26]([C:23]5[CH:24]=[CH:25][C:20]([Cl:19])=[CH:21][CH:22]=5)[N:27]=[CH:28][CH:29]=4)[CH:3]=[CH:4][C:5]=3[N:9]=[CH:8]2)=[C:11]([F:17])[CH:12]=1

Participants

3

Reactant 2

HCID 900950536-bromo-1-(4-chloro-2-fluoro-phenyl)-1H-benzo[d]imidazole2×HCID 900951261-(4-chloro-phenyl)-1H-pyrazol-5-ylboronic acid2×

Product 1

HCID 736718781-(4-Chloro-2-fluoro-phenyl)-6-[2-(4-chloro-phenyl)-2H-pyrazol-3-yl]-1H-benzoimidazole

Procedure

The title compound, white solid (23 mg, 18%), MS (ISP) m/z=423.4 [(M+H)+], mp 158° C., was prepared in accordance with the general method of example 1 from 6-bromo-1-(4-chloro-2-fluoro-phenyl)-1H-benzo[d]imidazole (intermediate M) (100 mg, 307 μmol) and 1-(4-chloro-phenyl)-1H-pyrazol-5-ylboronic acid (intermediate D) (82.1 mg, 369 μmol).

Sources & evidence

ORD record
ord-2f8f85e6cd8540d7b91e6db62c2a85ad
Source dataset
uspto-grants-2016_06
Patent number
US09365550B2

Reaction notes

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