2-Chloro-5-(trifluoromethyl)phenylboronic acid → 4-[4-(3,4-Dichloro-phenyl)-thiazol-2-yl]-2'-nitro-5'-trifluoromethyl-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.ClC1C=CC(C(F)(F)F)=CC=1B(O)O.[N+:39]([C:42]1[CH:47]=[CH:46][C:45]([C:48]([F:51])([F:50])[F:49])=[CH:44][C:43]=1B(O)O)([O-:41])=[O:40]>>[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:43]4[CH:44]=[C:45]([C:48]([F:51])([F:50])[F:49])[CH:46]=[CH:47][C:42]=4[N+:39]([O-:41])=[O:40])=[CH:6][CH:7]=3)[S:11][CH:12]=2)[CH:20]=[CH:19][C:18]=1[Cl:21]Participants
Reactant 3
Product 1
Procedure
Using the conditions of General Procedure A 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; 111 mg, 0.25 mmol) was reacted with 2-chloro-5-(trifluoromethyl)phenylboronic acid (2-nitro-5-trifluoromethylphenylboronic acid, pinacol ester (available from Combi-Blocks Inc.; 117 mg, 0.5 mmol). The resulting ester was hydrolyzed and the acid was purified to give 4-[4-(3,4-dichloro-phenyl)-thiazol-2-yl]-2′-nitro-5′-trifluoromethyl-biphenyl-2-carboxylic acid (31 mg, 23%). 1H NMR (300 MHz, DMSO-d6) δ 13.48 (s, 1H), 8.55 (d, J=1.7 Hz, 1H), 8.51 (s, 1H), 8.29-8.37 (m, 2H), 8.24 (d, J=8.3 Hz, 1H), 8.10 (dd, J=8.4, 2.0 Hz, 1H), 8.03 (s, 1H), 7.97 (d, J=8.5 Hz, 1H), 7.77 (d, J=8.5 Hz, 1H), 7.67 (d, J=8.1 Hz, 1H).
Workup
- customthe acid was purified
Sources & evidence
- ORD record
- ord-c329e7b0151e4da688887a608d3b0287
- Source dataset
- uspto-grants-2015_07
- Patent number
- US09073881B2
Reaction notes
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