2-Chlorophenylboronic acid → 4-(2-Chloro-phenyl)-2-(5,6-dimethoxy-benzoimidazol-1-yl)-thiazole-5-carboxylic acid
Reaction equation
C[O:2][C:3]([C:5]1[S:9][C:8]([N:10]2[C:14]3[CH:15]=[C:16]([O:21][CH3:22])[C:17]([O:19][CH3:20])=[CH:18][C:13]=3[N:12]=[CH:11]2)=[N:7][C:6]=1Br)=[O:4].[Cl:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1B(O)O>>[Cl:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[C:6]1[N:7]=[C:8]([N:10]2[C:14]3[CH:15]=[C:16]([O:21][CH3:22])[C:17]([O:19][CH3:20])=[CH:18][C:13]=3[N:12]=[CH:11]2)[S:9][C:5]=1[C:3]([OH:2])=[O:4]Participants
3
Procedure
In a similar manner as described for Example 26, 4-bromo-2-(5,6-dimethoxy-benzoimidazol-1-yl)-thiazole-5-carboxylic acid methyl ester (40 mg, 0.1 mmol) and 2-chlorophenylboronic acid (23.5 mg, 0.15 mmol) gave 4-(2-Chloro-phenyl)-2-(5,6-dimethoxy-benzoimidazol-1-yl)-thiazole-5-carboxylic acid (19.2 mg, 46%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 13.63 (br.s., 1 H); 8.82 (s, 1 H); 7.73 (s, 1 H); 7.59-7.65 (m, 2 H); 7.51 (td, 1 H); 7.46 (d, 1H); 7.39 (s, 1 H); 3.85 (s, 3 H); 3.81 (s, 3 H). MS m/z 416 (M+1).
Sources & evidence
- ORD record
- ord-0c432ad6e03a4d1ea75e44ac91761844
- Source dataset
- uspto-grants-2009_03
- Patent number
- US07504513B2
Reaction notes
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