Sodium Carbonate → 3-(4-Fluorophenyl)imidazo[1,2-a]pyridine-8-carboxylic acid

Participants

Reaction Steps

To a degassed (with Argon gas) solution of 3-iodo-imidazo[1,2-a]pyridine-8-carboxylic acid methyl ester (2.2 g, 7.3 mmol) and 4-fluorophenyl boronic acid (1.48 g, 9.44 mmol) in a 1:1 mixture of ethanol-benzene (100 mL) is added an aqueous solution of 2 M sodium carbonate (9 mL, 18 mmol) and tetrakis(triphenylphosphine) palladium (0) (0.42 g, 0.36 mmol) and the reaction mixture is warmed at reflux. After 16 hours, the reaction mixture is filtered through filter agent washing with EtOAc. The filtrate is diluted with water and the organic layer is separated. The pH of the aqueous layer is adjusted to 4-5 with 6 N aqueous HCl. The solid is collected by filtration and triturated with Et2O to afford the title compound. Mp: >400° C.

Provenance & Evidence