2-Methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol → Cyclopropyl[4-{4-[(dimethylamino)methyl]piperidin-1-yl}-6-(4-hydroxy-3-methoxyphenyl)quinolin-3-yl]methanone

HRID 2271723Notes

Reaction equation

HRID 2271723 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]([CH3:26])[CH3:25])[CH2:19][CH2:18]1.[CH3:27][O:28][C:29]1[CH:34]=[C:33](B2OC(C)(C)C(C)(C)O2)[CH:32]=[CH:31][C:30]=1[OH:44]>>[CH:14]1([C:12]([C:6]2[CH:7]=[N:8][C:9]3[C:4]([C:5]=2[N:17]2[CH2:22][CH2:21][CH:20]([CH2:23][N:24]([CH3:25])[CH3:26])[CH2:19][CH2:18]2)=[CH:3][C:2]([C:33]2[CH:32]=[CH:31][C:30]([OH:44])=[C:29]([O:28][CH3:27])[CH:34]=2)=[CH:11][CH:10]=3)=[O:13])[CH2:15][CH2:16]1

Participants

3

Reactant 2

HCID 27346502-Methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenolHCID 66715711(6-Bromo-4-{4-[(dimethylamino)methyl]piperidin-1-yl}quinolin-3-yl)(cyclopropyl)methanone

Product 1

HCID 66715179Cyclopropyl[4-{4-[(dimethylamino)methyl]piperidin-1-yl}-6-(4-hydroxy-3-methoxyphenyl)quinolin-3-yl]methanoneYield 45.3%

Procedure

Following general procedure D, (6-bromo-4-{4-[(dimethylamino)methyl]piperidin-1-yl}quinolin-3-yl)(cyclopropyl)methanone (47 mg, 0.113 mmol) was reacted with 2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (55 mg, 0.220 mmol) to afford the desired product (23.5 mg, 45%) as a yellow solid: 1H NMR (500 MHz, CD3OD) δ 8.81 (s, 1H), 8.29 (d, J=1.6 Hz, 1H), 8.10-8.00 (m, 2H), 7.30 (d, J=2.0 Hz, 1H), 7.22 (dd, J=8.2, 2.1 Hz, 1H), 6.94 (d, J=8.2 Hz, 1H), 3.97 (s, 3H), 3.56 (d, J=12.6 Hz, 2H), 3.27-3.15 (m, 4H), 2.95 (s, 6H), 2.65-2.55 (m, 1H), 2.15-2.25 (m, 1H), 1.95 (d, J=12.6 Hz, 2H), 1.78-1.67 (m, 2H), 1.38-1.28 (m, 2H), 1.28-1.19 (m, 2H); ESI MS m/z 460 [C28H33N3O3+H]+; HPLC 95.9% (AUC), tR=9.74 min.

Sources & evidence

ORD record
ord-a821a6ecaf48492ca3b879b0eb7b10cd
Source dataset
uspto-grants-2015_09
Patent number
US09120749B2

Reaction notes

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