Potassium Carbonate → HCID 66690711, compound

Participants

Reaction Conditions

Reaction Steps

A degassed solution of n-propanol (40 mL) and water (10 mL) was added to a mixture of ethyl 8-bromoimidazo[1,2-a]pyridine-6-carboxylate (1.0 g, 3.72 mmol), (4-methylphenyl)boronic acid (0.66 g, 4.83 mmol), (tetrakistriphenylphosphine) palladium(0) (0.22 g, 0.19 mmol) and potassium carbonate (1.54 g, 11.2 mmol). The mixture was heated to 90° C. After 18 h, sodium hydroxide (3N in water; 3 mL) and methanol (20 mL) was added. The mixture was stirred at 90° C. for another 48 h. The mixture was cooled to ambient temperature and filtered with Celite. The filtrate was concentrated. The water was azeotropically removed with repeated concentration from acetonitrile. The crude mixture was taken up in methanol and small amount of water and loaded onto a 25 g pre-equilibrated SCX column. The column was washed with 5× column volumes of methanol to remove impurities. The column was then washed with 3× column volumes of 2 M ammonia/methanol to elude the titled product (0.90 g): LC-MS [M+1]=253.2.

Provenance & Evidence