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

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Reaction Conditions

Reaction Steps

To a cold (−78° C.), stirred solution of 922 mg of 3-[(allyloxy)methyl]-N-(4-chlorobenzyl)-4-methyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide in 30 mL of dry THF, under argon, is added via cannula a THF solution of LDA, prepared in the usual manner from 1.3 mL of diisopropylamine and 2.7 mL of 2.5 M (hexanes) butyllithium in 20 mL of THF. The solution is stirred at −78° C. for 10 min, then 0.89 mL of dry DMF is added, and the mixture is allowed to warm to 0° C. After 10 min, aqueous workup (CHCl3/dil. HCl) is performed and is followed by flash chromatography on silica using 1.5% MeOH in CH2Cl2 to provide 620 mg of the title compound as a yellow-orange solid. Recrystallization from EtOAc gives yellow crystals.

Provenance & Evidence