Triethylamine → HCID 58404692, compound

Participants

Reaction Conditions

Reaction Steps

6-bromo-3-iodo-4-methoxypyrazolo[1,5-a]pyridine (50.0 mg, 0.142 mmol), cyclopropyl acetylene (0.018 ml, 0.212 mmol), tetrakis(triphenylphosphine)palladium (0) (16.4 mg, 0.014 mmol), and copper(I) iodide (4.1 mg, 0.02 mmol) were suspended in DMF (2 ml). Triethylamine (0.039 ml, 0.283 mmol) was added, the mixture was sparged with argon for 10 minutes, then heated to 60° C. overnight. LCMS analysis indicated incomplete reaction conversion. Cyclopropyl acetylene (0.018 ml, 0.212 mmol) was added and the mixture was stirred for 6 h, at which time, LCMS analysis indicated the reaction has proceeded further, but still conversion was still incomplete. Cyclopropyl acetylene (0.036 ml, 0.426 mmol) was added and the mixture was stirred overnight. The reaction mixture was diluted in ethyl acetate, washed with saturated aqueous sodium hydrogen carbonate and brine then dried over sodium sulfate, filtered and concentrated. The residue was purified by column chromatography on silica gel (ethyl acetate/isohexane gradient) to afford recovered 6-bromo-3-iodo-4-methoxypyrazolo[1,5-a]pyridine (faster eluting) along with 6-bromo-3-(cyclopropylethynyl)-4-methoxypyrazolo[1,5-a]pyridine (slower eluting).

Provenance & Evidence