Water → HCID 178491838, compound

Participants

Reaction Steps

183 mg (0.5 mmol) of [1-(2-Fluoro-5-methoxy-benzyl)-6,7-dimethoxy-isoquinolin-4-yl]-acetonitrile was dissolved in 15 mL toluene. The solution was warmed to 95 C. and 100 mg (1.53 mmol) of sodium azide and 210 mg (1.52 mmol) of triethyl amine hydrochloride was added and the mixture heated at 100 C for 60 minutes. Because ms and tlc suggest significant quantities of starting material is present an additional 100 mg of sodium azide and 210 mg of triethyl amine hydrochloride were added and heating at 100 C continued for 150 minutes at which time another 100 mg of sodium azide and 210 mg of triethyl amine hydrochloride and heating at 100 C continued for 120 minutes followed by room temperature stirring for 16 hours. The mixture was diluted with 15 mL of toluene and 20 mL of water. The stirring mixture was treated with 2 drops of conc. HCl in the fume hood and the resulting solid filtered giving ˜65 mg of the tetrazole as a white solid. The aqueous phase of the filtrate was separated and treated with stirring with another 2 drops of conc. HCl and solid filtered and washed with water to provide an additional 30 mg of the tetrazole. Thin layer chromatography show both crops to be homogeneous. Spectroscopy (nmr and ms) are compatible.

Provenance & Evidence