3-Vinylphenylboronic Acid (contains varying amounts of Anhydride) → 2-(5,6-Dimethoxy-benzoimidazol-1-yl)-4-(3-vinyl-phenyl)-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].[CH:24]([C:26]1[CH:27]=[C:28](B(O)O)[CH:29]=[CH:30][CH:31]=1)=[CH2:25]>>[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:30]4[CH:29]=[CH:28][CH:27]=[C:26]([CH:24]=[CH2:25])[CH:31]=4)[N:7]=3)[CH:11]=[N:12][C:13]=2[CH:18]=1Participants
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 3-vinylphenylboronic acid (22 mg, 0.15 mmol) gave 2-(5,6-Dimethoxy-benzoimidazol-1-yl)-4-(3-vinyl-phenyl)-thiazole-5-carboxylic acid (26 mg, 64%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.84 (s, 1 H); 8.04 (t, 1 H); 7.85 (s, 1 H); 7.83 (dt, 1 H); 7.59 (dt, 1 H); 7.48 (t, 1 H); 7.40 (s, 1 H); 6.83 (dd, 1 H); 5.92 (dd, 1 H); 5.33 (dd, 1H); 3.86 (s, 3 H); 3.85 (s, 3 H). MS 408 m/z (M+1).
Sources & evidence
- ORD record
- ord-c131f239de98446eb4a934f1e3e146c9
- Source dataset
- uspto-grants-2009_03
- Patent number
- US07504513B2
Reaction notes
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