3-Chloro-4-fluorophenylboronic Acid (contains varying amounts of Anhydride) → 4-(3-Chloro-4-fluoro-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:26]=[C:27](B(O)O)[CH:28]=[CH:29][C:30]=1[F:31]>>[Cl:24][C:25]1[CH:26]=[C:27]([C:6]2[N:7]=[C:8]([N:10]3[C:14]4[CH:15]=[C:16]([O:21][CH3:22])[C:17]([O:19][CH3:20])=[CH:18][C:13]=4[N:12]=[CH:11]3)[S:9][C:5]=2[C:3]([OH:2])=[O:4])[CH:28]=[CH:29][C:30]=1[F:31]Participants
3
Reactant 2
Product 1
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-chloro-4-fluorophenylboronic acid (26.2 mg, 0.15 mmol) gave 4-(3-Chloro-4-fluoro-phenyl)-2-(5,6-dimethoxy-benzoimidazol-1-yl)-thiazole-5-carboxylic acid (8.2 mg, 19%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 13.79 (br.s., 1H); 8.84 (s, 1 H,); 8.22 (dd, 1 H); 8.01 (ddd, 1 H); 7.81 (s, 1 H); 7.57 (t, 1H); 7.39 (s, 1 H); 3.87 (s, 3 H); 3.85 (s, 3 H). MS m/z 434 (M+1).
Sources & evidence
- ORD record
- ord-a43f73ea71054f398ab5c17438a8a78b
- Source dataset
- uspto-grants-2009_03
- Patent number
- US07504513B2
Reaction notes
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