Propargyl bromide → 1-[4-amino-2-ethoxymethyl-7-(prop-2-ynyloxy)-1H-imidazo[4,5-c]quinolin-1-yl]-2-methylpropan-2-ol

Participants

Reaction Steps

4-Amino-2-ethoxymethyl-1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c]quinolin-7-ol (2.35 g, 7.1 mmol), cesium carbonate (4.6 g, 14.2 mmol), and DMF (50 mL) were combined. Propargyl bromide (80% in toluene, 3.2 g, 21.3 mmol) was added and the reaction was stirred overnight. The reaction was poured into 500 mL of water and solid potassium carbonate was added to keep the mixture basic. A precipitate formed. Filtration of the reaction followed by air drying of the recovered solid provided 1.8 g of 1-[4-amino-2-ethoxymethyl-7-(prop-2-ynyloxy)-1H-imidazo[4,5-c]quinolin-1-yl]-2-methylpropan-2-ol as an off white powder.

Provenance & Evidence