Ethyl orthoformate → 6-Iodo-[1,2,4]triazolo[4,3-a]pyridine

Participants

Reaction Steps

A mixture of the product (2.0 g, 8.51 mmol) from Step A above in triethyl orthoformate (100 mL) was warmed at reflux for 18 h. After cooling to room temperature, the reaction mixture was concentrated under reduced pressure. The residue was dissolved in 250 mL of dichloromethane and was filtered through a pad of silica gel. The pad was washed with 20% methanol/dichloromethane to elute the compound from the silica gel, and this filtrate was concentrated to dryness and then redissolved in dichloromethane. Addition of hexanes afforded a precipitate, which was collected. The filtrate was concentrated to half volume, and was then diluted with additional hexanes to yield a second crop of product. The combined solids were dried in vacuo to afford the title compound as a pale yellow solid. LC/MS 246.0 (M+1)

Provenance & Evidence