m-Chloroperbenzoic acid → HCID 131721929, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 2,3-dimethyl-8-{2-[(2-methylsulfanylethoxy)carbonylamino]-6-methylbenzylamino}imidazo-[1,2-a]pyridine (1.0 g) in anhydrous dichloromethane (25 ml) is cooled to 0° C. and treated in portions with m-chloroperoxybenzoic acid (800 mg) and then stirred at 0° C. for a further 15 min. Aqueous sodium bicarbonate solution (25 ml) is then added, the mixture is stirred for a further 10 min, the organic phase is separated off and the aqueous phase is extracted with dichloromethane (3×20 ml). The combined organic phases are washed with water (50 ml), dried over magnesium sulfate and concentrated. To separate off the sulfone, the residue is chromatographed on silica gel (eluent: ethyl acetate/methanol/ammonia=19:1:0.1). The fractions of Rf =0.15 are collected and concentrated. The residue is taken up in a hot solution of fumaric acid (150 mg) in acetone (20 ml) and then cooled to 4° C. After filtration and drying in a high vacuum, 0.54 g (46%) of the title compound is isolated as a pale beige crystallizate. M.p. 137-138° C.

Provenance & Evidence