Tetrahydrofuran → HCID 18406865, compound

Participants

Reaction Conditions

Reaction Steps

Under argon atmosphere, ethyl[1,2,4]triazolo[1,5-a]pyridine-2-carboxylate (1 g, 5.23 mmol) was combined with THF (10 mL) at RT to give a brown suspension. Sodium borohydride (1.19 g, 31.4 mmol) was added in four portions. The mixture was heated to 65° C. for 15 min. After cooling down to RT, ethanol (10 mL) was added dropwise over a period of 15 min. The mixture was stirred at 65° C. for 4 h. The mixture was cooled down to 0-5° C. and NH4Cl (saturated aqueous solution, 20 mL) was added dropwise over a period of 10 min (foam!). Water (20 mL) was added and the yellow suspension was poured into dichloromethane (100 mL) and extracted with dichloromethane (4×75 mL). The combined organic layer was dried over MgSO4 and concentrated in vacuo to give the product as light yellow solid (720 mg, 4.76 mmol, 91%) which was used without further purification for the next step.

Provenance & Evidence