Ethyl orthoformate → 1-(7-bromo-1H-imidazo[4,5-c]quinolin-1-yl)-2-methylpropan-2-ol

Participants

Reaction Steps

A 2-L round bottom flask was charged with 1-[(3-amino-7-bromoquinolin-4-yl)amino]-2-methylpropan-2-ol (25.5 g, 82.2 mmol), toluene (1 L), pyridine-HCl (0.1 g, 0.82 mmol, 0.01 eq) and triethylorthoformate (13.4 g, 90.4 mmol, 1.1 eq), and the reaction was heated at reflux for 2 hours. The reaction mixture was concentrated to dryness. The resulting pale yellow solid was slurried in 1% aqueous sodium carbonate solution (250 mL), collected by vacuum filtration, and air-dried on the funnel overnight to provide 25 g of 1-(7-bromo-1H-imidazo[4,5-c]quinolin-1-yl)-2-methylpropan-2-ol.

Provenance & Evidence