Cesium carbonate → 2-[2-(4-Fluoro-2,3-dihydroindol-1-yl)-2-oxoethyl]-6-(2-fluoropyridin-4-yl)-3H-pyrimidin-4-one

Participants

Reaction Conditions

Reaction Steps

130 mg of 6-chloro-2-[2-(4-fluoro-2,3-dihydroindol-1-yl)-2-oxoethyl]-3H-pyrimidin-4-one, 3 ml of 1,4-dioxane, 104 mg of 2-fluoropyridine-4-boronic acid pinacol ester, 50 mg of tetrakis(triphenylphosphine)palladium(0), and 0.58 ml of an aqueous 1.5 M cesium carbonate solution are successively placed in a three-necked round-bottomed flask under argon and with stirring. The mixture is heated at a temperature of 100° C. for 20 hours, and then filtered while hot. After cooling to ambient temperature, the filtrate is concentrated to dryness under reduced pressure. The residue is taken up in a mixture of 20 ml of dichloromethane and 30 ml of water. After settling out, the organic phase is separated and the aqueous phase is extracted with dichloromethane. The aqueous phase is concentrated to dryness under reduced pressure. The residue is taken up in a mixture of 30 ml of ethyl acetate and a few drops of ethanol, and then washed with 5 ml of water. After settling out, the organic phase is separated and the aqueous phase is extracted with 2×20 ml of ethyl acetate. The organic extracts are combined, dried over magnesium sulfate, filtered, and then concentrated to dryness under reduced pressure. The residue is taken up in 1 ml of dioxane and the mixture is refluxed, and then filtered through sintered glass. After drying of the isolated solid, 44 mg of 2-[2-(4-fluoro-2,3-dihydroindol-1-yl)-2-oxoethyl]-6-(2-fluoropyridin-4-yl)-3H-pyrimidin-4-one are obtained in the form of a beige solid, the characteristics of which are the following:

Provenance & Evidence