(2-Chloro-5-methoxyphenyl)boronic acid → 2'-Chloro-4-[4-(3,4-dichloro-phenyl)-thiazol-2-yl]-5'-methoxy-biphenyl-2-carboxylic acid
Reaktionsgleichung
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.[Cl:25][C:26]1[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][C:27]=1B(O)O>>[Cl:25][C:26]1[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][C:27]=1[C:5]1[C:4]([C:3]([OH:2])=[O:24])=[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]=1Komponenten
3
Versuchsvorschrift
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-chloro-5-methoxyphenylboronic acid (available from Combi-Blocks Inc.; 75 mg, 0.4 mmol). The resulting ester was hydrolyzed and the acid was purified to give 2′-chloro-4-[4-(3,4-dichloro-phenyl)-thiazol-2-yl]-5′-methoxy-biphenyl-2-carboxylic acid (29 mg, 29%). 1H NMR (400 MHz, DMSO-d6) δ 13.04 (br s, 1H), 8.45-8.58 (m, 2H), 8.34 (d, J=2.0 Hz, 1H), 8.26 (dd, J=7.9, 1.9 Hz, 1H), 8.09 (dd, J=8.4, 1.9 Hz, 1H), 7.77 (d, J=8.5 Hz, 1H), 7.46 (d, J=8.0 Hz, 1H), 7.40 (d, J=8.8 Hz, 1H), 6.98 (dd, J=8.8, 3.0 Hz, 1H), 6.92 (d, J=3.0 Hz, 1H), 3.79 (m, 3H).