4-Methoxy-2-(trifluoromethyl)phenylboronic acid → HCID 71535529, compound
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[CH:32]=[CH:31][C:30](B(O)O)=[C:29]([C:36]([F:39])([F:38])[F:37])[CH:28]=1>>[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:30]4[CH:31]=[CH:32][C:27]([O:26][CH3:25])=[CH:28][C:29]=4[C:36]([F:37])([F:38])[F:39])=[CH:6][CH:7]=3)[S:11][CH:12]=2)[CH:20]=[CH:19][C:18]=1[Cl:21]Participants
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 4-methoxy-2-(trifluoromethyl)phenylboronic acid (available from Combi-Blocks Inc.; 110 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]-4′-methoxy-2′-trifluoromethyl-biphenyl-2-carboxylic acid (8 mg, 6%). 1H NMR (300 MHz, DMSO-d6) δ 12.97 (br s, 1H), 8.54 (s, 1H), 8.48 (s, 1H), 8.34 (s, 1H), 8.23 (d, J=7.5 Hz, 1H), 8.09 (d, J=8.7 Hz, 1H), 7.77 (d, J=8.5 Hz, 1H), 7.41 (d, J=7.9 Hz, 1H), 7.26 (s, 3H), 3.88 (s, 3H).
Workup
- customthe acid was purified
Sources & evidence
- ORD record
- ord-2c0abfd9781a410abf0c6599d554d295
- Source dataset
- uspto-grants-2015_07
- Patent number
- US09073881B2
Reaction notes
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