Acetonitrile → HCID 118071531, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 3-{2-[(difluoroacetyl)amino]ethyl}-5-hydroxy-N-methyl-1H-indole-2-carboxamide (103 mg), chloroacetonitrile (0.0313 mL), and acetonitrile (3.00 mL) were added cesium carbonate (377 mg) and tetrabutylammonium iodide (24.4 mg), followed by stirring at 60° C. for 3 hours. To the mixture was added chloroacetonitrile (0.0209 mL), followed by stirring at 60° C. for 1 hour. To this mixture was added water, followed by extraction with ethyl acetate, the organic layer was washed with saturated brine and subsequently dried over anhydrous sodium sulfate. The insoluble materials were separated by filtration, the filtrate was concentrated under reduced pressure, and then the obtained residue was purified by silica gel column chromatography (chloroform:methanol=100:0 to 94:6) to obtain a pale yellow solid. The obtained solid was washed with hexane:ethyl acetate=2:1 to obtain 5-(cyanomethoxy)-3-{2-[(difluoroacetyl)amino]ethyl}-N-methyl-1H-indole-2-carboxamide (5.00 mg) as a pale yellow solid.

Provenance & Evidence