2,3-Dihydroxybutanedioic Acid → 5-Formyl-2-methylthiazolo[5,4-b]pyridine

Participants

Reaction Conditions

Reaction Steps

To a suspension of the product of Step 4 (4.42 g, 25 mmol) in 100 mL of anhyd. THF at -78° C. was added dropwise 1.5M diisobutylaluminum hydride in toluene (40 mL) and the mixture was stirred at -78° C. for 2 hr. A solution of tartaric acid 10% was then added and the mixture was stirred at room temperature for 2 hr, neutralized with 10N NaOH and extracted with EtOAc. The title product was dried over Na2SO4 and purified by flash chromatography on silica with EtOAc:hexane 20:80 to yield 3.733 g (83%) as a white solid.

Provenance & Evidence