Carbon Disulfide → HCID 68663131, compound

Participants

Reaction Steps

A solution of 2-(2-phenylethyl)-1H-pyrrolo[2,3-b]pyridine-4-carbohydrazide (126 mg, 0.449 mmol), triethylamine (0.156 mL, 1.122 mmol) and carbon disulfide (0.136 mL, 2.246 mmol) in ethanol (10 mL) was stirred at 90° C. for 20 hr. The reaction mixture was concentrated under reduced pressure, and the residue was dissolved in N,N-dimethylformamide (5 mL). To this solution were added potassium carbonate (93 mg, 0.674 mmol) and 3-fluorobenzyl chloride (0.065 mL, 0.539 mmol), and the resulting mixture was stirred at room temperature for 3 hr. The reaction mixture was diluted with ethyl acetate, washed with water and saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=9/1-0/1) and basic silica gel column chromatography (hexane/ethyl acetate=9/1-0/1) and recrystallized from hexane/ethyl acetate to give the title compound (44 mg, yield 23%) as pale-yellow crystals.

Provenance & Evidence