4-Chlorophenylboronic acid → 4-(4-Chlorophenyl)-2-(3-fluoro-4-hydroxyphenyl)quinolin-6-ol

HRID 1867488Notes

Reaction equation

HRID 1867488 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])=[C:15]([F:20])[CH:14]=2)[CH:3]=1.[Cl:21][C:22]1[CH:27]=[CH:26][C:25](B(O)O)=[CH:24][CH:23]=1>>[Cl:21][C:22]1[CH:27]=[CH:26][C:25]([C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[C:9]([OH:12])[CH:10]=3)[N:5]=[C:4]([C:13]3[CH:18]=[CH:17][C:16]([OH:19])=[C:15]([F:20])[CH:14]=3)[CH:3]=2)=[CH:24][CH:23]=1

Participants

3

Reactant 2

HCID 742994-Chlorophenylboronic acidHCID 1354779434-Bromo-2-(3-fluoro-4-hydroxyphenyl)quinolin-6-ol

Product 1

HCID 1354403434-(4-Chlorophenyl)-2-(3-fluoro-4-hydroxyphenyl)quinolin-6-olYield 87%

Procedure

This compound was prepared from 6b using 4-chlorophenylboronic acid according to method P. Orange powder; Yield: 87%; mp 140-147° C.; 1H-NMR (400 MHz, DMSO-d6) δ 7.03 (d, J=2.7 Hz, 1H), 7.06 (t, J=8.8 Hz, 1H), 7.32 (dd, J=9.1, 2.7 Hz, 1H), 7.63 (d, J=8.8 Hz, 2H), 7.67 (d, J=8.7 Hz, 2H), 7.87 (s, 1H), 7.93-7.98 (m, 2H), 8.07 (dd, J=13.0, 2.1 Hz, 1H), 9.94 (s, 1H), 10.20 (s, 1H); MS (ESI) m/z 364/366 ([M−H]−), 366/368 ([M+H]+); Anal. Calcd for C21H13ClFNO2: C, 68.95; H, 3.58; N, 3.83. Found: C, 68.23; H, 3.54; N, 3.78.

Sources & evidence

ORD record
ord-6b46e0b3550d47d8afd2767e9077baf2
Source dataset
uspto-grants-2009_12
Patent number
US07632845B2

Reaction notes

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