6-Methoxypyridine-2-boronic acid → 5-[4-(3,4-Dichloro-phenyl)-thiazol-2-yl]-2-(6-methoxy-pyridin-2-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.[CH3:25][O:26][C:27]1[N:32]=[C:31](B(O)O)[CH:30]=[CH:29][CH:28]=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:31]4[CH:30]=[CH:29][CH:28]=[C:27]([O:26][CH3:25])[N:32]=4)=[C:4]([CH:9]=3)[C:3]([OH:24])=[O:2])[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 6-methoxypyridine-2-boronic acid (available from Combi-Blocks Inc.; 61 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-(6-methoxy-pyridin-2-yl)-benzoic acid (23 mg, 25%). 1H NMR (400 MHz, DMSO-d6) δ 12.95 (br s, 3H), 8.48 (s, 1H), 8.34 (d, J=2.0 Hz, 1H), 8.21 (dd, J=4.3, 2.3 Hz, 2H), 8.10 (dd, J=8.3, 2.0 Hz, 1H), 7.73-7.94 (m, 3H), 7.39 (d, J=7.3 Hz, 1H), 6.83 (d, J=8.0 Hz, 1H), 3.88 (s, 3H), 2.54 (s, 9H).
Workup
- customthe acid was purified
Sources & evidence
- ORD record
- ord-f18aef1f60e546e0899f1386f05b9b96
- Source dataset
- uspto-grants-2015_07
- Patent number
- US09073881B2
Reaction notes
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