3-Chloro-4-hydroxyphenylboronic Acid → HCID 66716406, compound

HRID 2271759Notes

Reaction equation

HRID 2271759 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]([N:23]2[CH2:28][CH2:27][N:26]([CH3:29])[CH2:25][CH2:24]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[CH2:22][CH2:21][CH:20]([N:23]3[CH2:28][CH2:27][N:26]([CH3:29])[CH2:25][CH2:24]3)[CH2:19][CH2:18]2)[CH:34]=[CH:35][C:36]=1[OH:37]

Participants

3

Reactant 2

HCID 221253733-Chloro-4-hydroxyphenylboronic AcidHCID 66715275HCID 66715275, compound

Product 1

HCID 66716406HCID 66716406, compoundYield 57.9%

Procedure

Following general procedure D, {6-bromo-4-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]quinolin-3-yl}(cyclopropyl)methanone (30 mg, 0.065 mmol) was reacted with 3-chloro-4-hydroxyphenylboronic acid (26 mg, 0.150 mmol) to afford the desired product (19 mg, 57%) as a yellow solid: 1H NMR (500 MHz, CD3OD) δ 8.76 (s, 1H), 8.28 (s, 1H), 8.06-7.98 (m, 2H), 7.71 (d, J=2.3 Hz, 1H), 7.54 (dd, J=8.4, 2.3 Hz, 1H), 7.09-7.03 (m, 1H), 3.55 (d, J=12.8 Hz, 2H), 3.34 (s, 3H), 3.23-3.15 (m, 2H), 2.81-2.50 (m, 8H), 2.35 (s, 3H), 2.12 (d, J=10.6 Hz, 2H), 1.92-1.81 (m, 2H), 1.34-1.28 (m, 2H), 1.27-1.20 (m, 2H); ESI MS m/z 505 [C29H33ClN4O4+H]+; HPLC>99% (AUC), tR=10.01 min.

Sources & evidence

ORD record
ord-d505b8794a634965a226763bbe6a6996
Source dataset
uspto-grants-2015_09
Patent number
US09120749B2

Reaction notes

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