4-Fluorophenylboronic acid → 3-Chloro-4-(4-fluorophenyl)-2-(4-hydroxyphenyl)quinolin-6-ol

HRID 1867494Notes

Reaction equation

HRID 1867494 reaction equation
Br[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([OH:12])[CH:10]=2)[N:5]=[C:4]([C:13]2[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=2)[C:3]=1[Cl:20].[F:21][C:22]1[CH:27]=[CH:26][C:25](B(O)O)=[CH:24][CH:23]=1>>[Cl:20][C:3]1[C:4]([C:13]2[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=2)=[N:5][C:6]2[C:11]([C:2]=1[C:25]1[CH:26]=[CH:27][C:22]([F:21])=[CH:23][CH:24]=1)=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=2

Participants

3

Reactant 2

HCID 2856454-Fluorophenylboronic acidHCID 1355026744-Bromo-3-chloro-2-(4-hydroxyphenyl)quinolin-6-ol

Product 1

HCID 1354426553-Chloro-4-(4-fluorophenyl)-2-(4-hydroxyphenyl)quinolin-6-olYield 95%

Procedure

This compound was prepared from 35a and 4-fluorophenylboronic acid according to method P. White solid; Yield: 95%; mp 295-296° C.; 1H-NMR (300 MHz, DMSO-d6) δ 6.55 (d, J=2.6 Hz, 1H), 6.87 (d, J=8.6 Hz, 2H), 7.31 (dd, J=9.1, 2.6 Hz, 1H), 7.45 (m, 4H), 7.57 (d, J=8.6 Hz, 2H), 7.92 (d, J=9.1 Hz, 1H), 9.73 (s, 1H), 10.07 (s, 1H); MS (ESI) m/z 364/366 ([M−H]−), 366/368 ([M+H]+); Anal. Calcd for C21H13ClFNO2: C, 68.96; H, 3.58; N, 3.83. Found: C, 68.19; H, 3.56; N, 3.74.

Sources & evidence

ORD record
ord-ffaba2dca67c4b0da3c07e42ba473e2d
Source dataset
uspto-grants-2009_12
Patent number
US07632845B2

Reaction notes

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