Dibah → HCID 57527233, compound

Participants

Reaction Steps

To a solution of ethyl 2-(isopropylamino)thiazolo[4,5-b]pyridine-6-carboxylate (0.278 g, 1.05 mmol) in toluene (10 mL) and THF (5 mL) was introduced Dibal-H (5.8 mL, 5.8 mmol) at −78° C. over 10 min. The resulting mixture was allowed to warm to rt and stirred for 4 hr. Additional Dibal-H (1.2 mL, 1.2 mmol) was added at rt, and the mixture was stirred for additional 1.5 hr before it was poured into ice-cold water (100 mL). The mixture was stirred at rt for 30 min, and then filtered through Celite® 545. The organic layer of filtrate was separated. The aqueous layer was basified with saturated NaHCO3 solution and extracted with AcOEt. The combined organic phase was washed with brine and dried over anhydrous MgSO4. Evaporation of solvent under vacuum gave the title compound as a viscous oil.

Provenance & Evidence