Hexane → 2-[2-(phenylsulfonyl)ethylthio]-N-(2-thienyl-methyl)-3-quinoline carboxamide

Participants

Reaction Conditions

Reaction Steps

112 mg (1.0 mmol) potassium tert-butylate were added to a solution of 202 mg (1.0 mmol) 2-(phenylsulfonyl)ethanethiol in DMF (6 ml) at 0° C. and the mixture was stirred for 10 min at 0° C. Then 303 mg (1.0 mmol) 2-chloro-N-(thiophen-2-ylmethyl)quinoline-3-carboxamide (precursor VVV01) were added at 0° C. and the reaction solution was heated slowly to 50° C. and stirred for 16 h at this temperature. After cooling to RT it was diluted with EE and washed with a saturated aqueous NH4Cl solution. The aqueous phase was extracted with EE. The combined organic phases were washed with water and brine, dried over Na2SO4, filtered and concentrated to small volume under vacuum. Column chromatography (hexane/EE 4:1) with the residue yielded 326 mg (0.7 mmol, 70%) 2-[2-(phenylsulfonyl)ethylthio]-N-(2-thienyl-methyl)-3-quinoline carboxamide. MS: m/z 469.1 [M+H]+.

Provenance & Evidence