3-Chloro-4-hydroxyphenylboronic Acid → 2-Chloro-4-[4-{4-[1-(dimethylamino)ethyl]piperidin-1-yl}-3-(methylsulfonyl)quinolin-6-yl]phenol
Reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([S:12]([CH3:15])(=[O:14])=[O:13])=[C:5]2[N:16]1[CH2:21][CH2:20][CH:19]([CH:22]([N:24]([CH3:26])[CH3:25])[CH3:23])[CH2:18][CH2:17]1.[Cl:27][C:28]1[CH:29]=[C:30](B(O)O)[CH:31]=[CH:32][C:33]=1[OH:34]>>[Cl:27][C:28]1[CH:29]=[C:30]([C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[N:8]=[CH:7][C:6]([S:12]([CH3:15])(=[O:14])=[O:13])=[C:5]3[N:16]2[CH2:17][CH2:18][CH:19]([CH:22]([N:24]([CH3:26])[CH3:25])[CH3:23])[CH2:20][CH2:21]2)[CH:31]=[CH:32][C:33]=1[OH:34]Participants
3
Procedure
Following general procedure D, 1-{1-[6-bromo-3-(methylsulfonyl)quinolin-4-yl]piperidin-4-yl}-N,N-dimethylethanamine (35 mg, 0.079 mmol) was reacted with 3-chloro-4-hydroxyphenylboronic acid (26 mg, 0.150 mmol) to afford the desired product (9.4 mg, 24%) as an off-white solid: 1H NMR (500 MHz, CD3OD) δ 9.23 (s, 1H), 8.39 (d, J=1.5 Hz, 1H), 8.24-8.13 (m, 2H), 7.74 (d, J=2.2 Hz, 1H), 7.58 (dd, J=8.4, 2.3 Hz, 1H), 7.09 (d, J=8.4 Hz, 1H), 3.81-3.70 (m, 2H), 3.55 (s, 2H), 3.45 (s, 3H), 3.28-3.22 (m, 1H), 2.84 (s, 6H), 2.14 (d, J=7.9 Hz, 1H), 1.95 (d, J=11.0 Hz, 2H), 1.87-1.68 (m, 2H), 1.38 (d, J=6.7 Hz, 3H); ESI MS m/z 488 [C25H30ClN3O3S+H]+; HPLC>99% (AUC), tR=10.84 min.
Sources & evidence
- ORD record
- ord-0c81bb9e9ffc4ea29d662fa69ce2e794
- Source dataset
- uspto-grants-2015_09
- Patent number
- US09120749B2
Reaction notes
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