Hydrochloric Acid → 3-(Azidomethyl)-N-(4-chlorobenzyl)-2-formyl-4-methyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide

Participants

Reaction Conditions

Reaction Steps

Into a cold (−78° C.), stirred mixture of 2.54 g of 3-(azidomethyl)-N-(4-chlorobenzyl)-4-methyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide in 100 mL of dry THF is added via cannula a solution of LDA in THF, prepared from 3.7 mL of diisopropylamine and 8.0 mL of 2.5 M (hexanes) butyllithium in 50 mL of THF. The mixture is stirred at −78° C. for 90 min, then 2.5 mL of dry DMF is added and the mixture is allowed to warm to 0° C. Aqueous workup (CHCl3/dil. HCl) followed by flash chromatography on silica using 2% MeOH in CH2Cl2 affords 1.61 g of the title compound as an amber foam.

Provenance & Evidence