3-Nitrophenylboronic Acid → 4-[4-(3,4-Dichloro-phenyl)-thiazol-2-yl]-3'-nitro-biphenyl-2-carboxylic 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.[N+:25]([C:28]1[CH:29]=[C:30](B(O)O)[CH:31]=[CH:32][CH:33]=1)([O-:27])=[O:26]>>[Cl:22][C:17]1[CH:16]=[C:15]([C:13]2[N:14]=[C:10]([C:8]3[CH:9]=[C:4]([C:3]([OH:2])=[O:24])[C:5]([C:32]4[CH:31]=[CH:30][CH:29]=[C:28]([N+:25]([O-:27])=[O:26])[CH:33]=4)=[CH:6][CH:7]=3)[S:11][CH:12]=2)[CH:20]=[CH:19][C:18]=1[Cl:21]Participants
3
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 3-nitrophenylboronic acid (available from Aldrich Chemical Company, Inc.; 67 mg, 0.4 mmol). The resulting ester was hydrolyzed and the acid was purified to give 4-[4-(3,4-dichloro-phenyl)-thiazol-2-yl]-3′-nitro-biphenyl-2-carboxylic acid (36 mg, 38%). 1H NMR (400 MHz, DMSO-d6) δ 8.46-8.51 (m, 2H), 8.18-8.39 (m, 4H), 8.06-8.15 (m, 1H), 7.87 (d, J=7.0 Hz, 1H), 7.73-7.79 (m, 2H), 7.63-7.68 (m, 1H).
Workup
- customthe acid was purified
Sources & evidence
- ORD record
- ord-b68dd252449945a8bf916fa708556642
- Source dataset
- uspto-grants-2015_07
- Patent number
- US09073881B2
Reaction notes
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