(3,4,5-Trifluorophenyl)boronic Acid (contains varying amounts of Anhydride) → 6-(trifluoromethyl)-2-(4-(3-(trifluoromethyl)pyridin-2-yl)-piperazin-1-yl)-4-(3,4,5-trifluorophenyl)-1H-benzo[d]imidazole

HRID 730830Notes

Reaction equation

HRID 730830 reaction equation
Br[C:2]1[C:10]2[N:9]=[C:8]([N:11]3[CH2:16][CH2:15][N:14]([C:17]4[C:22]([C:23]([F:26])([F:25])[F:24])=[CH:21][CH:20]=[CH:19][N:18]=4)[CH2:13][CH2:12]3)[NH:7][C:6]=2[CH:5]=[C:4]([C:27]([F:30])([F:29])[F:28])[CH:3]=1.[F:31][C:32]1[CH:33]=[C:34](B(O)O)[CH:35]=[C:36]([F:39])[C:37]=1[F:38]>>[F:29][C:27]([F:30])([F:28])[C:4]1[CH:3]=[C:2]([C:34]2[CH:33]=[C:32]([F:31])[C:37]([F:38])=[C:36]([F:39])[CH:35]=2)[C:10]2[N:9]=[C:8]([N:11]3[CH2:16][CH2:15][N:14]([C:17]4[C:22]([C:23]([F:26])([F:25])[F:24])=[CH:21][CH:20]=[CH:19][N:18]=4)[CH2:13][CH2:12]3)[NH:7][C:6]=2[CH:5]=1

Participants

3

Reactant 2

HCID 2734671(3,4,5-Trifluorophenyl)boronic Acid (contains varying amounts of Anhydride)HCID 116704454-Bromo-6-trifluoromethyl-2-[4-(3-trifluoromethylpyridin-2-yl)piperazin-1-yl]-1H-benzoimidazole

Product 1

HCID 115847496-(trifluoromethyl)-2-(4-(3-(trifluoromethyl)pyridin-2-yl)-piperazin-1-yl)-4-(3,4,5-trifluorophenyl)-1H-benzo[d]imidazole

Procedure

4-Bromo-6-trifluoromethyl-2-[4-(3-trifluoromethylpyridin-2-yl)piperazin-1-yl]-1H-benzoimidazole (1.99 g, 4 mmol, Example 7) reacted with 3,4,5-trifluorophenylboronic acid (1.1 g, 6 mmol, Lancaster) under the conditions of Example 51a to give the title compound as a white amorphous solid. MS (ESI, pos. ion) m/z: 546 (M+1).

Sources & evidence

ORD record
ord-b606c648424040dd87d7fd81436f687c
Source dataset
uspto-grants-2009_09
Patent number
US07582761B2

Reaction notes

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