Chlorotrimethylsilane → HCID 71279105, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 2-(3-phenyl-1-(pyridin-2-yl)-1H-1,2,4-triazol-5-yl)acetonitrile (28 mg, 96.4 μmol) in THF (1.5 mL) was, under argon atmosphere, cooled to 0-5° C. Trimethylchlorosilane (83.8 mg, 98.6 μL, 772 μmol) and lithium borohydride (2M solution in THF, 193 μL, 386 μmol) were consecutively added very slowly. The ice bath was removed after 10 min and the mixture was stirred at 60° C. for 1.5 h. The reaction mixture was cooled to 0-5° C. and MeOH (1 mL) was added slowly (bubbling!). After the temperature adjusted to RT, the mixture was poured into NaOH (1M aqueous solution, 15 mL) and was extracted with dichloromethane (2×25 mL) and ethyl acetate (1×25 mL). The combined organic phase was dried over MgSO4, filtered and evaporated to give the product as yellow waxy solid (18 mg, 67.8 μmol, 70%) which was used without further purification for the next step.

Provenance & Evidence