Diisopropylamine → N-(4-Chlorobenzyl)-2-formyl-3-[(2-methoxyethoxy)methyl]-4-methyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide

Participants

Reaction Conditions

Reaction Steps

A mixture of 210 mg of N-(4-chlorobenzyl)-3-[(2-methoxyethoxy)methyl]-4-methyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide and 5.0 mL of dry THF is heated to boiling under argon to dissolve the solid, then is cooled to −78° C. Into this mixture is cannulated a solution of LDA in THF, prepared in the usual manner from 0.35 mL of diisopropylamine and 0.80 mL of 2.5 M (in hexane) butyllithium in 4.0 mL of THF. The resulting deep blue mixture is stirred at −78° C. for 15 min, then 0.25 mL of dry DMF is added and the mixture allowed to warm to ambient temperature. The mixture is then partitioned between CH2Cl2 and dil HCl, and the organic phase dried (Na2SO4) and concentrated under reduced pressure. Flash chromatography on silica gel using 2% MeOH in CH2Cl2 provides 146 mg of the title compound as an orange solid. Recrystallization of a sample from EtOAc provides an analytical sample as a white solid.

Provenance & Evidence