(4-Cyano-2-methyl-phenyl)boronic acid → 4'-Cyano-4-[4-(3,4-dichloro-phenyl)-thiazol-2-yl]-2'-methyl-biphenyl-2-carboxylic acid
반응식
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][C:26]1[CH:31]=[C:30]([C:32]#[N:33])[CH:29]=[CH:28][C:27]=1B(O)O>>[C:32]([C:30]1[CH:29]=[CH:28][C:27]([C:5]2[C:4]([C:3]([OH:2])=[O:24])=[CH:9][C:8]([C:10]3[S:11][CH:12]=[C:13]([C:15]4[CH:20]=[CH:19][C:18]([Cl:21])=[C:17]([Cl:22])[CH:16]=4)[N:14]=3)=[CH:7][CH:6]=2)=[C:26]([CH3:25])[CH:31]=1)#[N:33]참가 물질
실험 절차
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-methyl-4-cyanophenylboronic acid (available from Aldrich Chemical Company, Inc.; 64 mg, 0.4 mmol). The resulting ester was hydrolyzed and the acid was purified to give 4′-cyano-4-[4-(3,4-dichloro-phenyl)-thiazol-2-yl]-2′-methyl-biphenyl-2-carboxylic acid (13 mg, 14%). 1H NMR (400 MHz, DMSO-d6) δ 13.14 (br s, 1H), 8.54 (d, J=2.0 Hz, 1H), 8.49 (s, 1H), 8.34 (d, J=2.0 Hz, 1H), 8.28 (dd, J=8.0, 2.0 Hz, 1H), 8.09 (dd, J=8.5, 2.0 Hz, 1H), 7.75-7.83 (m, 2H), 7.71 (d, J=7.8 Hz, 1H), 7.41 (d, J=8.0 Hz, 1H), 7.31 (d, J=8.0 Hz, 1H).
후처리
- customthe acid was purified
출처 및 근거
- ORD 기록
- ord-1a1d264416124f9980032084f7a5ded6
- 출처 데이터셋
- uspto-grants-2015_07
- 특허 번호
- US09073881B2
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