3-Chloro-4-hydroxyphenylboronic Acid → HCID 66715921, compound

HRID 2271753Notes

Reaction equation

HRID 2271753 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[CH2:29][CH2:28][O:27][CH2:26][CH2:25]2)[CH2:19][CH2:18]1.[Cl:30][C:31]1[CH:32]=[C:33](B(O)O)[CH:34]=[CH:35][C:36]=1[OH:37]>>[Cl:30][C:31]1[CH:32]=[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[CH2:15][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][O:27][CH2:28][CH2:29]3)[CH2:21][CH2:22]2)[CH:34]=[CH:35][C:36]=1[OH:37]

Participants

3

Reactant 2

HCID 221253733-Chloro-4-hydroxyphenylboronic AcidHCID 66715423HCID 66715423, compound

Product 1

HCID 66715921HCID 66715921, compoundYield 62%

Procedure

Following general procedure D, {6-bromo-4-[4-(morpholinomethyl)piperidin-1-yl]quinolin-3-yl}(cyclopropyl)methanone (30 mg, 0.065 mmol) was reacted with 3-chloro-4-hydroxyphenylboronic acid (34 mg, 0.200 mmol) to afford the desired product (20.3 mg, 62%) as an off-white solid: 1H NMR (500 MHz, CD3OD) δ 8.73 (s, 1H), 8.29 (s, 1H), 8.04-7.98 (m, 2H), 7.71 (d, J=2.3 Hz, 1H), 7.54 (dd, J=8.4, 2.3 Hz, 1H), 7.07 (d, J=8.4 Hz, 1H), 3.74-3.71 (m, 3H), 3.53 (d, J=12.7 Hz, 2H), 3.34 (s, 3H), 3.26-3.15 (m, 2H), 2.59-2.46 (m, 4H), 2.38 (d, J=6.7 Hz, 2H), 1.98 (d, J=12.9 Hz, 3H), 1.66-1.52 (m, 2H), 1.36-1.27 (m, 2H), 1.27-1.20 (m, 2H); ESI MS m/z 506 [C29H32ClN3O3+H]+; HPLC 98.0% (AUC), tR=10.44 min.

Sources & evidence

ORD record
ord-79cc127d89d04947b3718005f122cfde
Source dataset
uspto-grants-2015_09
Patent number
US09120749B2

Reaction notes

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