3,4-Dimethoxyphenylboronic acid → 2-(5,6-Dimethoxy-benzoimidazol-1-yl)-4-(3,4-dimethoxy-phenyl)-thiazole-5-carboxylic acid

HRID 1785491Notes

Reaction equation

HRID 1785491 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].[CH3:24][O:25][C:26]1[CH:27]=[C:28](B(O)O)[CH:29]=[CH:30][C:31]=1[O:32][CH3:33]>>[CH3:20][O:19][C:17]1[C:16]([O:21][CH3:22])=[CH:15][C:14]2[N:10]([C:8]3[S:9][C:5]([C:3]([OH:2])=[O:4])=[C:6]([C:29]4[CH:28]=[CH:27][C:26]([O:25][CH3:24])=[C:31]([O:32][CH3:33])[CH:30]=4)[N:7]=3)[CH:11]=[N:12][C:13]=2[CH:18]=1

Participants

3

Reactant 2

HCID 27347023,4-Dimethoxyphenylboronic acidHCID 575958514-Bromo-2-(5,6-dimethoxy-benzoimidazol-1-yl)-thiazole-5-carboxylic acid methyl ester

Product 1

HCID 236538202-(5,6-Dimethoxy-benzoimidazol-1-yl)-4-(3,4-dimethoxy-phenyl)-thiazole-5-carboxylic acidYield 60%

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 3,4-dimethoxyphenylboronic acid (27.3 mg, 0.15 mmol) gave 2-(5,6-Dimethoxy-benzoimidazol-1-yl)-4-(3,4-dimethoxy-phenyl)-thiazole-5-carboxylic acid (26.4 mg, 60%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 13.45 (br.s., 1 H); 8.83 (s, 1 H); 7.86 (s, 1 H); 7.66 (d, 1 H); 7.60 (dd, 1 H); 7.40 (s, 1 H); 7.08 (d, 1H); 3.87 (s, 3 H); 3.85 (s, 3 H); 3.84 (s, 3 H); 3.82 (s, 3 H). MS m/z 442 (M+1).

Sources & evidence

ORD record
ord-950ff29ccb2f4da8b36cb7e8427e747f
Source dataset
uspto-grants-2009_03
Patent number
US07504513B2

Reaction notes

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