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

HRID 2202469Notes

Reaction equation

HRID 2202469 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][C:11]=3[F:17])[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:17][C:11]1[CH:12]=[C:13]([F:16])[CH:14]=[CH:15][C:10]=1[N:7]1[C:6]2[CH:18]=[C:2]([C:30]3[N:26]([C:23]4[CH:24]=[CH:25][C:20]([F:19])=[CH:21][CH:22]=4)[N:27]=[CH:28][CH:29]=3)[CH:3]=[CH:4][C:5]=2[N:9]=[CH:8]1

Participants

3

Reactant 2

HCID 900951701-(4-Fluorophenyl)-1H-pyrazol-5-ylboronic acid2×HCID 900954196-bromo-1-(2,4-difluoro-phenyl)-1H-benzo[d]imidazole2×

Product 1

HCID 736736721-(2,4-Difluoro-phenyl)-6-[2-(4-fluoro-phenyl)-2H-pyrazol-3-yl]-1H-benzoimidazole

Procedure

The title compound, light brown solid (69 mg, 55%), MS (ISP) m/z=391.5 [(M+H)+], mp 152° C., was prepared in accordance with the general method of example 1 from 6-bromo-1-(2,4-difluoro-phenyl)-1H-benzo[d]imidazole (intermediate K) (100 mg, 324 μmol) and 1-(4-fluoro-phenyl)-1H-pyrazol-5-ylboronic acid (intermediate A) (79.9 mg, 388 μmol).

Sources & evidence

ORD record
ord-c98cbfc7dac5411fa4ab1a515777ad2c
Source dataset
uspto-grants-2016_06
Patent number
US09365550B2

Reaction notes

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