Sodium Carbonate → HCID 58923880, compound

Participants

Reaction Conditions

Reaction Steps

Sodium carbonate (0.140 g, 1.32 mmol), triphenylphosphine (74.7 mg, 0.33 mmol), 3-pyridine boronic acid (0.149 g, 1.21 mmol), and palladium (II) acetate (25 mg, 0.11 mmol) were sequentially added to a solution of 3-bromo-9-(methylsulfonyl)-9,10,11,12-tetrahydro-8H-[1,4]diazepino[1′,2′:1,2]imidazo[4,5-c]quinolin-6-amine (0.450 g, 1.1 mmol) in n-propanol (15 mL), methanol (10 mL), and water (5 mL). The reaction was heated at 80° C. overnight and then concentrated under reduced pressure. The residue was mixed with dichloromethane, and the resulting solid was isolated by filtration. The solid was purified by column chromatography on silica gel (eluting with 2 N ammonia in methanol/chloroform in a gradient from 0% to 25%. The resulting solid was mixed with material from another run and purified again by column chromatography on silica gel under the same conditions to provide 76.8 mg of 9-(methylsulfonyl)-3-pyridin-3-yl-9,10,11,12-tetrahydro-8H-[1,4]diazepino[1′,2′:1,2]imidazo[4,5-c]quinolin-6-amine, as a beige solid, mp 302° C.

Provenance & Evidence