Trimethyl orthoformate → HCID 67778750, compound

Participants

Reaction Steps

6-fluoropyridin-3-amine (1.12 g, 10 mmol), sodium azide (0.98 g, 15 mmol) and trimethylorthoformate (1.7 g, 16 mmol) were added to acetic acid (20 mL), and stirred at room temperature over night. The reaction was heated to 120° C. reflux for 7 hours. The reaction was cooled down to room temperature, poured into ice water (50 mL), extracted with ethyl acetate (50 mL), second wash with sodium hydroxide (1N, 20 mL). The organic phase was dried by magnesium sulfate, filtered, concentrated and purified by column chromatography through a 80 gram Analogix™ silica gel cartridge eluting with 50% ethyl acetate/hexanes to give the title compound as a white solid.

Provenance & Evidence