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-(pyrrolidin-1-ylmethyl)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]([CH2:23][N:24]2[CH2:28][CH2:27][CH2:26][CH2:25]2)[CH2:19][CH2:18]1.[Cl:29][C:30]1[CH:35]=[C:34](B2OC(C)(C)C(C)(C)O2)[CH:33]=[C:32]([O:45][CH3:46])[C:31]=1[OH:47]>>[Cl:29][C:30]1[CH:35]=[C:34]([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[CH2:15][CH2:16]2)=[O:13])=[C:5]3[N:17]2[CH2:18][CH2:19][CH:20]([CH2:23][N:24]3[CH2:25][CH2:26][CH2:27][CH2:28]3)[CH2:21][CH2:22]2)[CH:33]=[C:32]([O:45][CH3:46])[C:31]=1[OH:47]Participants
3
Reactant 2
Product 1
Procedure
Following general procedure D, {6-bromo-4-[4-(pyrrolidin-1-ylmethyl)piperidin-1-yl]quinolin-3-yl}(cyclopropyl)methanone (30 mg, 0.068 mmol) was reacted with 2-chloro-6-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (30 mg, 0.106 mmol) to afford the desired product (21.5 mg, 61%) as a yellow solid: 1H NMR (500 MHz, CD3OD) δ 8.76 (s, 1H), 8.29 (s, 1H), 8.07-7.99 (m, 2H), 7.31 (d, J=2.0 Hz, 1H), 7.24 (d, J=2.0 Hz, 1H), 3.99 (s, 3H), 3.54 (d, J=12.4 Hz, 2H), 3.22 (t, J=11.7 Hz, 2H), 2.82 (s, 4H), 2.71 (d, J=6.5 Hz, 2H), 2.60-2.51 (m, 1H), 2.06-1.81 (m, 7H), 1.71-1.59 (m, 2H), 1.36-1.27 (m, 2H), 1.27-1.19 (m, 2H); ESI MS m/z 520 [C30H34ClN3O3+H]+; HPLC 98.6% (AUC), tR=10.70 min.
Sources & evidence
- ORD record
- ord-aa7bc77179104952b4a4a4a7924e9210
- Source dataset
- uspto-grants-2015_09
- Patent number
- US09120749B2
Reaction notes
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