Hydrochloric Acid → HCID 66653630, compound

Participants

Reaction Conditions

Reaction Steps

0.248 g (1.38 mmol) of [4-(methoxycarbonyl)phenyl]boronic acid, 0.57 g (2.30 mmol) of potassium carbonate in 2 ml of water, and 0.027 g (0.02 mmol) of tetrakis(triphenylphosphine)palladium are added to a solution of 0.43 g (1.15 mmol) of methyl 2-amino-5-[(1-bromoimidazo[1,5-a]pyridin-3-yl)carbonyl]benzoate in 10 ml of DME, under an inert argon atmosphere. The reaction medium is heated at 90° C. for 2 hours. The reaction medium is acidified with a 1N aqueous solution of hydrochloric acid, and extracted with dichloromethane. The organic phase is washed with water, dried over sodium sulphate, filtered, and concentrated under reduced pressure. The solid obtained is dissolved in 5 ml of DMF. 30 μl (0.5 mmol) of methyl iodide and 0.052 g (0.16 mmol) of caesium carbonate are added. After stirring for 24 hours at ambient temperature, the reaction medium is hydrolysed with water and then extracted with ethyl acetate. The organic phase is dried over sodium sulphate, filtered, and then concentrated under reduced pressure. The solid obtained is taken up in methanol. After filtration and drying overnight at 50° C. under reduced pressure, 0.379 g of a yellow powder is obtained.

Provenance & Evidence