Stannane, tributyl(1-ethoxyethenyl)- → HCID 60142164, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of Example 41i.e. (E)-2-(4-bromophenyl)-N,N-diisopentyl-3-(3-(piperidin-1-yl)prop-1-en-1-yl)pyrazolo[1,5-a]pyridine-5-carboxamide (553 mg, 0.954 mmol) in toluene (14 mL) was added tributyl(1-ethoxy-vinyl)tin (1.03 g, 2.86 mmol) and tetrakis(triphenylphosphine) palladium (O) (55 mg, 0.05 mmol). The mixture was degassed by bubbling nitrogen into it for 10 minutes and was then heated to 120° C. for 4 h. The mixture was allowed to cool to room temperature and concentrated to a residue and dissolved in THF (12 mL). 1N HCl (3 mL) was added and the mixture was stirred at room temperature for 1 h. Sodium bicarbonate was slowly added until pH was reached 8-9 and the mixture was extracted with ethyl acetate (2×30 mL). The combined organics were washed with brine, filtered and concentrated under reduced pressure.

Provenance & Evidence