Sodium hydride → HCID 11778364, compound

Participants

Reaction Steps

NaH (39 mg, 0.95 mmol) was added to a solution of the above ester (210 mg, 0.95 mmol) in THF (15 mL) at room temperature. After stirring for 5 min, α-bromoacetamide (134 mg, 0.97 mmol) and n-Bu4NI (10 mg) were added. The mixture was stirred at room temperature for 1 h, then NaH (39 mg, 0.95 mmol) was added, and the mixture was stirred for an additional 0.5 h. The reaction was quenched by addition of saturated aqueous NH4Cl, diluted with EtOAc, washed with brine, dried over Na2SO4, and concentrated giving an orange solid. The crude residue was recrystallized from MeOH giving 3-amino-2-carbamoyl-6-methyl-thieno[2,3-b]pyridine-4-carboxylic acid ethyl ester (160 mg, 60%), m.p. 205-208° C.

Provenance & Evidence