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

HRID 2202464Notes

Reaction equation

HRID 2202464 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]([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>>[Cl: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 900950726-bromo-1-(4-chloro-phenyl)-1H-benzo[d]imidazole2×HCID 900952401-(4-trifluoromethyl-phenyl)-1H-pyrazol-5-ylboronic acid2×

Product 1

HCID 736735601-(4-Chloro-phenyl)-6-[2-(4-trifluoromethyl-phenyl)-2H-pyrazol-3-yl]-1H-benzoimidazole

Procedure

The title compound, light brown solid (56 mg, 39%), MS (ISP) m/z=439.4 [(M+H)+], mp 198° 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-trifluoromethyl-phenyl)-1H-pyrazol-5-ylboronic acid (intermediate C) (91.6 mg, 358 μmol).

Sources & evidence

ORD record
ord-26795d3fc32542c695c39daf29ee2f0f
Source dataset
uspto-grants-2016_06
Patent number
US09365550B2

Reaction notes

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