Chloromethyl methyl sulfide → HCID 23442452, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of sodium hydride (60-72% in mineral oil, 225 mg, 5.6 mmol), which was washed with hexane and dried in vacuo, in N,N-dimethylformamide (40 ml) was added a solution of 1,7-dimethyl-1,4-dihydro-9H-pyrazolo[4,3-b]quinolin-9-one (EXAMPLE 47, step 2, 0.80 g, 3.75 mmol) in N,N-dimethylformamide at 0° C. The mixture was stirred at 0° C. for 10 min and at room temperature for 2 h. Chloromethyl methyl sulfide (0.87 ml, 7.5 mmol) was added at 0° C. and the mixture was stirred at room temperature for 10.5 h. Further more, sodium hydride (60-72% in mineral oil, 68 mg, 2.8 mmol) and chloromethyl methyl sulfide (0.87 ml, 7.5 mmol) were added. After 2 h, the mixture was heated at 50° C. for 15.5 h. The mixture was poured into brine (50 ml) and extracted with ethyl acetate (50 ml×2). The organic extracts were dried over magnesium sulfate and concentrated. Purification by column chromatography on silica gel eluting with ethyl acetate/hexane (1:1) gave 0.46 g (43%) of the title compound as a pale yellow solid.

Provenance & Evidence