Triethylsilane → HCID 117843806, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (4-(benzyloxy)-6-chloropyrazolo[1,5-a]pyridin-3-yl)methanol (274 mg, 0.946 mmol) in TFA (3.0 mL) was added triethylsilane (0.604 mL, 3.78 mmol). The reaction was stirred at 60° C. overnight. Incomplete removal of the benzyl group was observed. The reaction was concentrated, dissolved in HBr (48%, 3.5 ml) and the reaction was heated at 100° C. overnight. The reaction was cooled and neutralized by the addition of 2N NaOH. The aqueous layer was extracted with EtOAc (3×) and the combined organics were washed with saturated NaHCO3 (aq), brine, dried (MgSO4), filtered and concentrated to provide 6-chloro-3-methylpyrazolo[1,5-a]pyridin-4-ol. LCMS-ES I+(m/z): [M+H]+ calcd for C8H7ClN2O: 183.0; found 183.0.

Provenance & Evidence