2-(Phenylsulfonyl)ethanethiol → 2-[2-(benzenesulfonyl)ethylthio]-6-fluoro-N-(2-thienylmethyl)-nicotinamide

HRID 660062

Reaktionsgleichung

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

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

258 mg (2.3 mmol) of potassium tert-butoxide were added at 0° C. to a solution of 465 mg (2.3 mmol) of 2-(phenylsulfonyl)ethanethiol in DMF (7 ml). After stirring for 10 min at 0° C., 381 mg (1.5 mmol) of 2,6-difluoro-N-(thiophen-2-ylmethyl)nicotinamide were added and the mixture was then heated for 16 hours at 50° C. Dilution with EA and washing with brine were then carried out. The organic phase was dried over Na2SO4, filtered and concentrated in vacuo. CC (hexane/EA 7:3) of the residue yielded 298 mg (0.68 mmol, 45%) of 2-[2-(benzenesulfonyl)ethylthio]-6-fluoro-N-(2-thienylmethyl)-nicotinamide. MS: m/z 437.0 [M+H]+

Aufarbeitung

temperaturethe mixture was then heated for 16 hours at 50° C
washDilution with EA and washing with brine
dry with materialThe organic phase was dried over Na2SO4
filtrationfiltered
concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag: ord-f9f850e0595945c9bcd595132ffacc8e
Quelldatensatz: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08084470B2

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