2-Methoxypyridine-3-boronic acid hydrate → 5-[4-(3,4-Dichloro-phenyl)-thiazol-2-yl]-2-(2-methoxy-pyridin-3-yl)-benzoic acid
Reaction equation
C[O:2][C:3](=[O:24])[C:4]1[CH:9]=[C:8]([C:10]2[S:11][CH:12]=[C:13]([C:15]3[CH:20]=[CH:19][C:18]([Cl:21])=[C:17]([Cl:22])[CH:16]=3)[N:14]=2)[CH:7]=[CH:6][C:5]=1Br.O.[CH3:26][O:27][C:28]1[C:33](B(O)O)=[CH:32][CH:31]=[CH:30][N:29]=1>>[Cl:22][C:17]1[CH:16]=[C:15]([C:13]2[N:14]=[C:10]([C:8]3[CH:7]=[CH:6][C:5]([C:33]4[C:28]([O:27][CH3:26])=[N:29][CH:30]=[CH:31][CH:32]=4)=[C:4]([CH:9]=3)[C:3]([OH:2])=[O:24])[S:11][CH:12]=2)[CH:20]=[CH:19][C:18]=1[Cl:21]Participants
Procedure
Using the conditions of General Procedure B for Suzuki Coupling and Hydrolysis in Parallel Mode, 2-bromo-5-[4-(3,4-dichloro-phenyl)-thiazol-2-yl]-benzoic acid methyl ester (which may be prepared as described for Intermediate 6; 89 mg, 0.2 mmol) was reacted with and 2-methoxypyridine-3-boronic acid hydrate (available from Combi-Blocks Inc.; 68 mg, 0.4 mmol). The resulting ester was hydrolyzed and the acid was purified to give 5-[4-(3,4-dichloro-phenyl)-thiazol-2-yl]-2-(2-methoxy-pyridin-3-yl)-benzoic acid (11 mg, 12%). 1H NMR (300 MHz, DMSO-d6) δ 12.94 (br s, 1H), 8.47 (s, 1H), 8.41 (d, J=1.9 Hz, 1H), 8.33 (d, J=2.1 Hz, 1H), 8.25 (dd, J=8.0, 2.0 Hz, 1H), 8.18 (dd, J=5.0, 1.8 Hz, 1H), 8.09 (dd, J=8.5, 2.1 Hz, 1H), 7.77 (d, J=8.3 Hz, 1H), 7.70 (dd, J=7.3, 1.8 Hz, 1H), 7.52 (d, J=7.9 Hz, 1H), 7.10 (dd, J=7.2, 5.1 Hz, 1H), 3.78 (s, 3H).
Workup
- customthe acid was purified
Sources & evidence
- ORD record
- ord-a5eec305551f41bca59e50a2766b724b
- Source dataset
- uspto-grants-2015_07
- Patent number
- US09073881B2
Reaction notes
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