1-(4-chloro-phenyl)-1H-pyrazol-5-ylboronic acid → 6-[2-(4-Chloro-phenyl)-2H-pyrazol-3-yl]-1-(4-fluoro-phenyl)-1H-benzoimidazole

HRID 2202463Notes

Reaction equation

HRID 2202463 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]([F:16])=[CH:12][CH:11]=3)[C:6]=2[CH:17]=1.[Cl: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:18][C:19]1[CH:20]=[CH:21][C:22]([N:25]2[C:29]([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]([F:16])=[CH:12][CH:11]=5)[C:6]=4[CH:17]=3)=[CH:28][CH:27]=[N:26]2)=[CH:23][CH:24]=1

Participants

3

Reactant 2

HCID 900951261-(4-chloro-phenyl)-1H-pyrazol-5-ylboronic acid2×HCID 900951396-bromo-1-(4-fluoro-phenyl)-1H-benzo[d]imidazole2×

Product 1

HCID 736735596-[2-(4-Chloro-phenyl)-2H-pyrazol-3-yl]-1-(4-fluoro-phenyl)-1H-benzoimidazole

Procedure

The title compound, off-white solid (28 mg, 21%), MS (ISP) m/z=389.4 [(M+H)+], mp 180° C., was prepared in accordance with the general method of example 1 from 6-bromo-1-(4-fluoro-phenyl)-1H-benzo[d]imidazole (intermediate G) (100 mg, 344 μmol) and 1-(4-chloro-phenyl)-1H-pyrazol-5-ylboronic acid (intermediate D) (84.0 mg, 378 μmol).

Sources & evidence

ORD record
ord-b320ec0a750e42858697e46d7314f10b
Source dataset
uspto-grants-2016_06
Patent number
US09365550B2

Reaction notes

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