Potassium Carbonate → 2-(2-(Phenylsulfonyl)ethylthio)-6-(trifluoromethyl)quinoline-3-carboxylic acid

HRID 1949153Notes

Reaction equation

C([O-])([O-])=O.[K+].[K+].[C:7]1([S:13]([CH2:16][CH2:17][SH:18])(=[O:15])=[O:14])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.Cl[C:20]1[C:29]([C:30]([OH:32])=[O:31])=[CH:28][C:27]2[C:22](=[CH:23][CH:24]=[C:25]([C:33]([F:36])([F:35])[F:34])[CH:26]=2)[N:21]=1>CC(C)=O>[C:7]1([S:13]([CH2:16][CH2:17][S:18][C:20]2[C:29]([C:30]([OH:32])=[O:31])=[CH:28][C:27]3[C:22](=[CH:23][CH:24]=[C:25]([C:33]([F:34])([F:36])[F:35])[CH:26]=3)[N:21]=2)(=[O:15])=[O:14])[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

Conditions

Temperature: 70 °C

Procedure

206 mg (1.5 mmol) K2CO3 and 303 mg (1.5 mmol) 2-(phenylsulfonyl)ethanethiol were added to a solution of 827 mg (1.0 mmol) 2-chloro-6-(trifluoromethyl)quinoline-3-carboxylic acid (precursor VVV03) in acetone (3 ml) and the mixture was heated for 5 h at 70° C. Then it was filtered and the filtrate was concentrated to small volume under vacuum. The residue was dissolved in water and acidified with a 1N hydrochloric acid. It was then extracted with EE and the organic phase was dried over Na2SO4, filtered and concentrated to small volume under vacuum. Crystallisation (DCM/hexane) of the residue yielded 316 mg (0.7 mmol, 72%) 2-(2-(phenylsulfonyl)ethylthio)-6-(trifluoromethyl)quinoline-3-carboxylic acid.

Workup

filtrationThen it was filtered
concentrationthe filtrate was concentrated to small volume under vacuum
dissolutionThe residue was dissolved in water
extractionIt was then extracted with EE
dry with materialthe organic phase was dried over Na2SO4
filtrationfiltered
concentrationconcentrated to small volume under vacuum
customCrystallisation (DCM/hexane) of the residue

Sources & evidence

ORD record: ord-88758ace43f74dcdb759344c5a002fd1
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08399673B2

Reaction notes

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