Chloroform → 6-Fluoro-2-(7-(2-methoxyethoxy)imidazo[1,2-a]pyridin-3-yl)quinolin-8-ol

Participants

Reaction Conditions

Reaction Steps

6-Fluoro-2-(2-methoxyvinyl)-8-(triisopropylsilyloxy)quinoline (2.5 g, 6.6 mmol) was dissolved in THF (10.3 mL) and water (2.6 mL) and cooled to 0° C. The solution was treated dropwise with a solution of freshly recrystallized N-bromosuccinimide (1.24 g, 6.99 mmol) dissolved in THF (7 mL) and water (1.75 mL). The reaction was stirred at 0° C. for 20 minutes then warmed and stirred at ambient temperature for 2.5 hours. The reaction was treated with 4-(2-methoxyethoxy)pyridin-2-amine (1.12 g, 6.65 mmol) and the mixture was heated to reflux overnight. The mixture was cooled and solids formed in the flask. Chloroform (50 mL), ethyl acetate (300 mL), and water (50 mL) were added to disperse the solids and the undissolved solids were collected by filtration and washed with ethyl acetate and water, then air-dried, (1.2 g). MS APCI (+) m/z 354.1 (M+1) detected.

Provenance & Evidence