Diisopropylamine → Thieno[3,2-c]pyridin-2-amine

Participants

Reaction Conditions

Reaction Steps

To a cold (-70° C.) stirred solution of lithium diisopropylamide in THF, prepared in situ by reaction of 3.63 g of freshly distilled diisopropylamine and 22 ml of 1.6M n-butyl lithium in 50 ml of hexane, were added dropwise over twenty minutes 4.05 g (30 mMoles) of thieno[3,2-c]pyridine in 20 ml of THF. The reaction mixture was stirred for twenty minutes following the addition, and then was diluted by the dropwise addition of 5.22 g (36 mMoles) of α-azido styrene in 20 ml of THF. The reaction mixture was stirred for two hours while maintaining the temperature at -70° to -50° C.; and then for an additional hour while allowing the temperature to warm to -15° C. The reaction was then quenched by the addition of 50 ml of 5% aqueous hydrochloric acid. Removal of the reaction solvent by evaporation under reduced pressure afforded 3.0 g of crude product. Purification by chromatography over silica gel, eluting with ethyl acetate, afforded 1.2 g of 2-aminothieno[3,2-c]pyridine. Mass Spec. M+ theory: 150, found: 150.

Provenance & Evidence