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

HRID 2202462Notes

Reaction equation

HRID 2202462 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.[F:18][C:19]([F:35])([F:34])[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:16][C:13]1[CH:14]=[CH:15][C:10]([N:7]2[C:6]3[CH:17]=[C:2]([C:30]4[N:26]([C:23]5[CH:22]=[CH:21][C:20]([C:19]([F:18])([F:34])[F:35])=[CH:25][CH:24]=5)[N:27]=[CH:28][CH:29]=4)[CH:3]=[CH:4][C:5]=3[N:9]=[CH:8]2)=[CH:11][CH:12]=1

Participants

3

Reactant 2

HCID 900951396-bromo-1-(4-fluoro-phenyl)-1H-benzo[d]imidazole2×HCID 900952401-(4-trifluoromethyl-phenyl)-1H-pyrazol-5-ylboronic acid2×

Product 1

HCID 736735581-(4-Fluoro-phenyl)-6-[2-(4-trifluoromethyl-phenyl)-2H-pyrazol-3-yl]-1H-benzoimidazole

Procedure

The title compound, yellow solid (45 mg, 31%), MS (ISP) m/z=423.5 [(M+H)+], mp 167° 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-trifluoromethyl-phenyl)-1H-pyrazol-5-ylboronic acid (intermediate C) (96.7 mg, 378 μmol).

Sources & evidence

ORD record
ord-be1ac6835a704bf491d6bcd787e0b2ab
Source dataset
uspto-grants-2016_06
Patent number
US09365550B2

Reaction notes

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