3-Chloro-4-hydroxyphenylboronic Acid → [6-(3-Chloro-4-hydroxyphenyl)-4-{4-[(dimethylamino)methyl]piperidin-1-yl}quinolin-3-yl](cyclopropyl)methanone

HRID 2271725Notes

Reaction equation

HRID 2271725 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.[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]([CH:14]2[CH2:16][CH2:15]2)=[O:13])=[C:5]3[N:17]2[CH2:18][CH2:19][CH:20]([CH2:23][N:24]([CH3:26])[CH3:25])[CH2:21][CH2:22]2)[CH:31]=[CH:32][C:33]=1[OH:34]

Participants

3

Reactant 2

HCID 221253733-Chloro-4-hydroxyphenylboronic AcidHCID 66715711(6-Bromo-4-{4-[(dimethylamino)methyl]piperidin-1-yl}quinolin-3-yl)(cyclopropyl)methanone

Product 1

HCID 86692920[6-(3-Chloro-4-hydroxyphenyl)-4-{4-[(dimethylamino)methyl]piperidin-1-yl}quinolin-3-yl](cyclopropyl)methanoneYield 59%

Procedure

Following general procedure D, (6-bromo-4-{4-[(dimethylamino)methyl]piperidin-1-yl}quinolin-3-yl)(cyclopropyl)methanone (25 mg, 0.060 mmol) was reacted with 3-chloro-4-hydroxyphenylboronic acid (21 mg, 0.120 mmol) to afford the desired product (16.3 mg, 59%) as an off-white solid: 1H NMR (500 MHz, CD3OD) δ 8.74 (s, 1H), 8.28 (s, 1H), 8.05-7.98 (m, 2H), 7.70 (d, J=2.3 Hz, 1H), 7.53 (dd, J=8.4, 2.3 Hz, 1H), 7.06 (d, J=8.4 Hz, 1H), 3.53 (d, J=12.7 Hz, 2H), 3.21 (t, J=11.5 Hz, 2H), 2.60-2.51 (m, 1H), 2.43 (d, J=6.8 Hz, 2H), 2.35 (s, 6H), 2.00-1.84 (m, 3H), 1.65-1.53 (m, 2H), 1.34-1.28 (m, 2H), 1.28-1.17 (m, 2H); ESI MS m/z 464 [C27H30ClN3O2+H]+; HPLC>99% (AUC), tR=10.38 min.

Sources & evidence

ORD record
ord-eb8aca17bf344c64abf67ff08bdf26b0
Source dataset
uspto-grants-2015_09
Patent number
US09120749B2

Reaction notes

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