2-Chloro-6-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol → [6-(3-Chloro-4-hydroxy-5-methoxyphenyl)-4-{4-[1-(dimethylamino)ethyl]piperidin-1-yl}quinolin-3-yl](cyclopropyl)methanone
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]([CH:14]1[CH2:16][CH2:15]1)=[O:13])=[C:5]2[N:17]1[CH2:22][CH2:21][CH:20]([CH:23]([N:25]([CH3:27])[CH3:26])[CH3:24])[CH2:19][CH2:18]1.[Cl:28][C:29]1[CH:34]=[C:33](B2OC(C)(C)C(C)(C)O2)[CH:32]=[C:31]([O:44][CH3:45])[C:30]=1[OH:46]>>[Cl:28][C:29]1[CH:34]=[C:33]([C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[N:8]=[CH:7][C:6]([C:12]([CH:14]2[CH2:16][CH2:15]2)=[O:13])=[C:5]3[N:17]2[CH2:22][CH2:21][CH:20]([CH:23]([N:25]([CH3:27])[CH3:26])[CH3:24])[CH2:19][CH2:18]2)[CH:32]=[C:31]([O:44][CH3:45])[C:30]=1[OH:46]Participants
Reactant 2
Product 1
Procedure
Following general procedure F, (6-bromo-4-{4-[1-(dimethylamino)ethyl]piperidin-1-yl}quinolin-3-yl)(cyclopropyl)methanone (50 mg, 0.116 mmol) was reacted with 2-chloro-6-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (49 mg, 0.173 mmol) to afford the desired product (33 mg, 56%) as a yellow-green solid: 1H NMR (500 MHz, CD3OD) δ 8.74 (s, 1H), 8.30 (d, J=1.6 Hz, 1H), 8.07-7.97 (m, 2H), 7.32 (d, J=2.1 Hz, 1H), 7.25 (d, J=2.1 Hz, 1H), 4.00 (s, 3H), 3.55 (d, J=12.2 Hz, 2H), 3.19 (dd, J=19.9, 7.2 Hz, 2H), 2.64-2.58 (m, 1H), 2.58-2.50 (m, 1H), 2.40 (s, 6H), 2.03 (d, J=12.7 Hz, 1H), 1.95-1.78 (m, 3H), 1.73-1.61 (m, 2H), 1.33-1.28 (m, 2H), 1.26-1.20 (m, 2H), 1.11 (d, J=6.6 Hz, 3H); ESI MS m/z 508 [C29H34ClN3O3+H]+; HPLC 97.0% (AUC), tR=10.04 min.
Sources & evidence
- ORD record
- ord-67689336eaff4b5e83d0a9204fd2a1bf
- Source dataset
- uspto-grants-2015_09
- Patent number
- US09120749B2
Reaction notes
Loading…