Triethylamine → HCID 69084207, compound

Participants

Reaction Conditions

Reaction Steps

A thick walled glass tube, equipped with a stir bar, was charged with palladium (II) acetate (50 mg, 0.22 mmol), acetonitrile (50 mL), triethylamine (1.80 mL, 13.0 mmol), tri-o-tolylphosphine (200 mg, 0.65 mmol), N,N-dimethylacrylamide (511 mg, 5.16 mmol) and 1-(7-bromo-2-ethyl-1H-imidazo[4,5-c]quinolin-1-yl)-2-methylpropan-2-ol (1.50 g, 4.30 mmol). The reaction mixture was purged with nitrogen and the tube was sealed and heated at 120° C. in an oil bath. The reaction was maintained at 120° C. for 18 hours and then cooled to ambient temperature. Upon cooling a precipitate formed that was dissolved by the addition of methanol and chloroform. The remaining insoluble material was removed by filtration through a 0.2 micron PTFE membrane filter. The filtrate was concentrated under reduced pressure and purified by chromatography using a HORIZON HPFC system (silica, eluting with a 0-25% gradient of CMA in chloroform). The resulting product was washed with 1% aqueous sodium carbonate and filtered to provide 1.37 g of 3-[2-ethyl-1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c]quinolin-7-yl]-N,N-dimethylprop-2-enamide as an off-white solid, mp 196-198° C.

Provenance & Evidence