Triethylamine → HCID 21949250, compound

Participants

Reaction Steps

N1-Propyl-5-(2-amino-4-pyridyl)oxy-1H-1-indolecarboxamide (477 mg, 1.54 mmol) was suspended in tetrahydrofuran (5 ml) at room temperature; triethylamine (0.536 mg, 3.08 mmol) and phenyl chloroformate (0.389 ml, 3.85 mmol) was added thereto while stirring; and the reaction mixture was stirred at room temperature for 2 hours. Water was added to the reaction mixture; this was subjected to extraction with ethyl acetate, washed with brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. N,N-dimethylformamide (3 ml) and pyrrolidine (0.27 ml, 3.23 mmol) was added to the residue; and the reaction mixture was stirred at room temperature overnight. The reaction mixture was partitioned between ethyl acetate and water; and the organic layer was dried over anhydrous sodium sulfate. The solution was concentrated under reduced pressure; the residue was purified by silica gel column chromatography (Fuji Silysia NH, ethyl acetate-methanol). The resultant was washed with a solvent mixture of ether:hexane=1:1; and the solid was filtered off to yield crystals (40 mg) of the title compound.

Provenance & Evidence