3,5-Dichloropyridine → HCID 19072377, compound

Participants

Reaction Steps

Potassium tert-butoxide (12.7) was added to a 0° C. solution of N-aminoindole (6.0 g) in 1-methyl-2-pyrrolidinone (150 ml). After stirring for thirty minutes, 3,5-dichloropyridine (7.5 g) was added and the resulting mixture was stirred at room temperature for five hours. The reaction mixture was quenched with water, diluted with ethyl acetate (500 ml) and washed with brine (3×500 ml). The organic layer was dried over anhydrous sodium sulfate and concentrated in vacuo to give an oil. Purification of the oil by flash chromatography (silica, 0-2% methanol/dichloromethane) afforded the title compound (11.1 g), m.p. 154°-156° C.

Provenance & Evidence