3-Chloro-4-hydroxyphenylboronic Acid → 1-{6-(3-Chloro-4-hydroxyphenyl)-4-[4-(diethylamino)cyclohexylamino]quinolin-3-yl}ethanone
Reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([C:12](=[O:14])[CH3:13])=[C:5]2[NH:15][CH:16]1[CH2:21][CH2:20][CH:19]([N:22]([CH2:25][CH3:26])[CH2:23][CH3:24])[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]([C:12](=[O:14])[CH3:13])=[C:5]3[NH:15][CH:16]2[CH2:21][CH2:20][CH:19]([N:22]([CH2:25][CH3:26])[CH2:23][CH3:24])[CH2:18][CH2:17]2)[CH:31]=[CH:32][C:33]=1[OH:34]Participants
3
Procedure
Following general procedure D, 1-{6-bromo-4-[4-(diethylamino)cyclohexylamino]quinolin-3-yl}ethanone (30 mg, 0.072 mmol) was reacted with 3-chloro-4-hydroxyphenylboronic acid (34 mg, 0.200 mmol) to afford the desired product (19.7 mg, 59%) as a yellow-brown solid: 1H NMR (500 MHz, CD3OD) δ 8.95 (s, 1H), 8.34 (d, J=1.8 Hz, 1H), 8.02 (dd, J=8.7, 1.9 Hz, 1H), 7.91 (d, J=8.7 Hz, 1H), 7.71 (d, J=2.3 Hz, 1H), 7.53 (dd, J=8.4, 2.3 Hz, 1H), 7.06 (d, J=8.4 Hz, 1H), 4.31 (s, 1H), 3.52-3.43 (m, 1H), 3.22 (q, J=7.2 Hz, 4H), 2.70 (s, 3H), 2.46 (d, J=12.3 Hz, 2H), 2.20 (d, J=11.9 Hz, 2H), 1.88-1.65 (m, 4H), 1.41-1.30 (m, 6H); ESI MS m/z 466 [C27H32ClN3O2+H]+; HPLC 97.7% (AUC), tR=10.44 min.
Sources & evidence
- ORD record
- ord-bac39690e9b649c2bf928af755e0dba7
- Source dataset
- uspto-grants-2015_09
- Patent number
- US09120749B2
Reaction notes
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