4-Fluorophenylboronic acid → 7-Chloro-3-(4-chloro-benzenesulfonyl)-4-(4-fluoro-phenyl)-quinoline

HRID 561046Notes

Reaction equation

Br[C:2]1[C:11]2[C:6](=[CH:7][C:8]([Cl:12])=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[S:13]([C:16]1[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=1)(=[O:15])=[O:14].[F:23][C:24]1[CH:29]=[CH:28][C:27](B(O)O)=[CH:26][CH:25]=1>COCCOC.C(=O)([O-])[O-].[Na+].[Na+]>[Cl:12][C:8]1[CH:7]=[C:6]2[C:11]([C:2]([C:27]3[CH:28]=[CH:29][C:24]([F:23])=[CH:25][CH:26]=3)=[C:3]([S:13]([C:16]3[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=3)(=[O:15])=[O:14])[CH:4]=[N:5]2)=[CH:10][CH:9]=1

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of 4-bromo-7-chloro-3-(4-chloro-benzenesulfonyl)-quinoline (0.42 g, 1 mmol), 4-fluorophenylboronic acid (0.21 g, 1.5 mmol) and tetrakis-(triphenylphosphin)palladium(0) (0.08 g, 0.07 mmol) in 30 ml 1,2-dimethoxyethane and 8 ml of 2M aqueous sodium carbonate solution was stirred for 2 hours at 70° C. After cooling the mixture was concentrated in vacuo. The crude residue was purified by column chromatography on silica gel (Kieselgel 60, eluent: chloroform) and crystallized from methanol to obtain 0.29 g of the title compound in 67% yield.

Workup

temperatureAfter cooling the mixture
concentrationwas concentrated in vacuo
customThe crude residue was purified by column chromatography on silica gel (Kieselgel 60, eluent: chloroform)
customcrystallized from methanol

Sources & evidence

ORD record: ord-0a25ebb70ce944ccb556e2193e04c014
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08063220B2

Reaction notes

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