3-Chloro-4-hydroxyphenylboronic Acid → {6-(3-Chloro-4-hydroxyphenyl)-4-[4-(diethylamino)cyclohexylamino]quinolin-3-yl}(cyclopropyl)methanone

HRID 2271738Notes

Reaction equation

HRID 2271738 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[NH:17][CH:18]1[CH2:23][CH2:22][CH:21]([N:24]([CH2:27][CH3:28])[CH2:25][CH3:26])[CH2:20][CH2:19]1.[Cl:29][C:30]1[CH:31]=[C:32](B(O)O)[CH:33]=[CH:34][C:35]=1[OH:36]>>[Cl:29][C:30]1[CH:31]=[C:32]([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[NH:17][CH:18]2[CH2:19][CH2:20][CH:21]([N:24]([CH2:25][CH3:26])[CH2:27][CH3:28])[CH2:22][CH2:23]2)[CH:33]=[CH:34][C:35]=1[OH:36]

Participants

3

Reactant 2

HCID 221253733-Chloro-4-hydroxyphenylboronic AcidHCID 66716442{6-Bromo-4-[4-(diethylamino)cyclohexylamino]quinolin-3-yl}(cyclopropyl)methanone

Product 1

HCID 68091924{6-(3-Chloro-4-hydroxyphenyl)-4-[4-(diethylamino)cyclohexylamino]quinolin-3-yl}(cyclopropyl)methanoneYield 33.4%

Procedure

Following general procedure F, {6-bromo-4-[4-(diethylamino)cyclohexylamino]quinolin-3-yl}(cyclopropyl)methanone (65 mg, 0.146 mmol) was reacted with 3-chloro-4-hydroxyphenyl boronic acid (38 mg, 0.219 mmol) to afford the desired product (24 mg, 33%) as a light yellow-brown solid: 1H NMR (500 MHz, CD3OD) δ 9.29 (s, 0.5H), 9.20 (s, 0.5H), 8.38 (s, 1H), 8.12-8.04 (m, 1H), 7.98-7.91 (m, 1H), 7.74 (d, J=2.3 Hz, 0.5H), 7.68 (d, J=2.3 Hz, 0.5H), 7.58-7.48 (m, 1H), 7.06 (dd, J=9.5, 8.5 Hz, 1H), 3.59-3.49 (m, 1H), 3.45-3.15 (m, 4H), 2.98-2.83 (m, 1H), 2.45 (d, J=11.9 Hz, 1H), 2.30-2.19 (m, 2H), 2.11-1.88 (m, 4H), 1.86-1.70 (m, 2H), 1.38 (q, J=7.4 Hz, 6H), 1.27-1.20 (m, 2H), 1.19-1.10 (m, 2H); ESI MS m/z 492 [C29H34ClN3O2+H]+; HPLC 97.5% (AUC), tR=4.53 min.

Sources & evidence

ORD record
ord-3063b5319bfc4a6abe3ee7ccae4dd711
Source dataset
uspto-grants-2015_09
Patent number
US09120749B2

Reaction notes

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