4-(Dimethylamino)phenylboronic acid → (4-{2-[(2R)-4-(3-Chloro-pyridin-2-yl)-2-methyl-piperazin-1-yl]-6-trifluoromethyl-3H-benzoimidazol-4-yl}-phenyl)-dimethyl-amine

HRID 912979Notes

Reaction equation

HRID 912979 reaction equation
Br[C:2]1[C:7]2[NH:8][C:9]([N:11]3[CH2:16][CH2:15][N:14]([C:17]4[C:22]([Cl:23])=[CH:21][CH:20]=[CH:19][N:18]=4)[CH2:13][C@H:12]3[CH3:24])=[N:10][C:6]=2[CH:5]=[C:4]([C:25]([F:28])([F:27])[F:26])[CH:3]=1.[CH3:29][N:30]([C:32]1[CH:37]=[CH:36][C:35](B(O)O)=[CH:34][CH:33]=1)[CH3:31]>>[Cl:23][C:22]1[C:17]([N:14]2[CH2:15][CH2:16][N:11]([C:9]3[NH:8][C:7]4[C:2]([C:35]5[CH:36]=[CH:37][C:32]([N:30]([CH3:31])[CH3:29])=[CH:33][CH:34]=5)=[CH:3][C:4]([C:25]([F:28])([F:27])[F:26])=[CH:5][C:6]=4[N:10]=3)[C@H:12]([CH3:24])[CH2:13]2)=[N:18][CH:19]=[CH:20][CH:21]=1

Participants

3

Reactant 2

HCID 27343444-(Dimethylamino)phenylboronic acidHCID 178461521HCID 178461521, compound

Product 1

HCID 178461525(4-{2-[(2R)-4-(3-Chloro-pyridin-2-yl)-2-methyl-piperazin-1-yl]-6-trifluoromethyl-3H-benzoimidazol-4-yl}-phenyl)-dimethyl-amine

Procedure

7-Bromo-2-[(2R)-4-(3-chloropyridin-2-yl)-2-methylpiperazin-1-yl]-5-(trifluoromethyl)-1H-benzoimidazole (95 mg, 0.2 mmol, Example 77) and 4-(N,N-dimethylamino)phenylboronic acid (41 mg, 0.25 mmol, Aldrich) reacted under the conditions of Example 51a to give the title compound as a white amorphous solid. MS (ESI, pos. ion) m/z: 515 (M+1).

Sources & evidence

ORD record
ord-d03edc4908704e008d06033c94bbd7fa
Source dataset
uspto-grants-2011_09
Patent number
US08026241B2

Reaction notes

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