3-Fluorophenylboronic acid → 7-(1-tert-Butylpiperidin-4-yl)-1-(2,6-dichlorophenyl)-5-(4-fluorophenyl)quinolin-2(1H)-one
Reaction equation
Br[C:2]1[CH:11]=[C:10]([C:12]2[CH2:13][CH2:14][N:15]([C:18]([CH3:21])([CH3:20])[CH3:19])[CH2:16][CH:17]=2)[CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6](=[O:30])[N:7]2[C:22]1[C:27]([Cl:28])=[CH:26][CH:25]=[CH:24][C:23]=1[Cl:29].[F:31][C:32]1[CH:33]=[C:34](B(O)O)[CH:35]=[CH:36][CH:37]=1>>[C:18]([N:15]1[CH2:14][CH2:13][CH:12]([C:10]2[CH:9]=[C:8]3[C:3]([CH:4]=[CH:5][C:6](=[O:30])[N:7]3[C:22]3[C:27]([Cl:28])=[CH:26][CH:25]=[CH:24][C:23]=3[Cl:29])=[C:2]([C:35]3[CH:34]=[CH:33][C:32]([F:31])=[CH:37][CH:36]=3)[CH:11]=2)[CH2:17][CH2:16]1)([CH3:19])([CH3:21])[CH3:20]Participants
3
Procedure
The title compound was prepared from 5-bromo-7-(1-tert-butyl-1,2,3,6-tetrahydropyridin-4-yl)-1-(2,6-dichlorophenyl)quinolin-2(1H)-one (INTERMEDIATE ABA5) and using 3-fluorophenylboronic acid as described in EXAMPLE ABA11. 1H NMR (CD3OD, 500 MHz): δ 1.272 (s, 9H), 1.700 (bs, 2H), 1.742 (bs, 2H), 2.520-2.818 (bs, 3H), 3.379 (bs, 2H), 6.478 (s, 1H), 6.710 (d, J=10.0 Hz, 1H), 7.228 (s, 1H), 7.264 (m, 1H), 7.420 (m, 2H), 7.618 (t, J=7.6 Hz, 1H), 7.722 (m, 2H), 7.975 (d, J=10.0 Hz, 1H). Mass spectrum (ESI): 541.5 (M+1).
Sources & evidence
- ORD record
- ord-10f08b1e515549acb3679b2b4ada50ae
- Source dataset
- uspto-grants-2004_10
- Patent number
- US06809199B2
Reaction notes
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