4-Cyanophenylboronic acid → 4-(4-Cyanophenyl)-2-(3-fluoro-4-hydroxyphenyl)quinolin-6-ol
Reaction equation
Br[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([OH:12])[CH:10]=2)[N:5]=[C:4]([C:13]2[CH:18]=[CH:17][C:16]([OH:19])=[C:15]([F:20])[CH:14]=2)[CH:3]=1.[C:21]([C:23]1[CH:28]=[CH:27][C:26](B(O)O)=[CH:25][CH:24]=1)#[N:22]>>[C:21]([C:23]1[CH:28]=[CH:27][C:26]([C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[C:9]([OH:12])[CH:10]=3)[N:5]=[C:4]([C:13]3[CH:18]=[CH:17][C:16]([OH:19])=[C:15]([F:20])[CH:14]=3)[CH:3]=2)=[CH:25][CH:24]=1)#[N:22]Participants
3
Procedure
This compound was prepared from 6b using 4-cyanophenylboronic acid according to method P. Yellow powder; Yield: 52%; mp 266-267° C.; 1H-NMR (400 MHz, DMSO-d6) δ 6.97 (d, J=2.7 Hz, 1H), 7.07 (t, J=8.8 Hz, 1H), 7.34 (dd, J=9.0, 2.6 Hz, 1H), 7.82 (d, J=8.5 Hz, 2H), 7.92 (s, 1H), 7.95-8.00 (m, 2H), 8.07-8.10 (m, 3H), 10.00 (s, 1H), 10.21 (s, 1H); MS (ESI) m/z 355 ([M−H]−), 357 ([M+H]+); Anal. Calcd for C22H13FN2O2: C, 74.15; H, 3.68; N, 7.86. Found: C, 73.69; H, 3.53; N, 7.86.
Sources & evidence
- ORD record
- ord-92dc4e67d045456d8fb5219c00c0e78f
- Source dataset
- uspto-grants-2009_12
- Patent number
- US07632845B2
Reaction notes
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