Triethylamine → HCID 21984387, compound

Participants

Reaction Steps

8-Bromo-1-isobutyl-1H-imidazo[4,5-c]quinolin-4-amine (22.0 g, 68.9 mmol), triethylamine (19.20 mL, 137.8 mmol), dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium (II) dichloromethane (1.00 g, 1.37 mmol), and potassium vinyltrifluoroborate (10.15 g, 75.81 mmol) were dissolved in n-propanol (20 mL/g). The amber colored solution was heated at reflux temperature for 18 hours and then cooled to ambient temperature. The reaction was concentrated under reduced pressure. The resulting solid was slurried in 1% aqueous sodium carbonate and a fine powder was collected by filtration. The powder was sequentially washed with acetonitrile (5 mL/g) and 10% sodium hydroxide (500 mL). A final purification using a HORIZON HPFC system (silica cartridge, eluting with 4% methanol/dichloromethane) provided 10 g of 1-isobutyl-8-vinyl-1H-imidazo[4,5-c]quinolin-4-amine as an off-white solid, MS (APCI) m/z 267 (M+H)+.

Provenance & Evidence