Water → 5-(3-methoxyphenyl)-2-(3-pyridylmethyl)-1H-isoindole-1,3 (2H)-dione

Participants

Reaction Steps

To a solution of 1.80 g of zinc chloride in 8.8 ml of tetrahydrofuran was added 8.8 ml of tetrahydrofuran solution (1.0M) of 3-methoxyphenylmagnesium bromide, and the resultant mixture was stirred at room temperature for 20 minutes. This solution was added to a mixture of 2.27 g of 2-(3-pyridylmethyl)-5-(trifluoromethanesulfonyloxy)-1H-isoindole-1,3 (2H)-dione, 27 mg of palladium acetate, 131 mg of 1,1'-bis(diphenylphosphino)ferrocene and 18 ml of tetrahydrofuran and stirred at room temperature for 17 hours. After finishing the reaction, the mixture was mixed with water under ice cooling and shaken with ethyl acetate. The organic layer was washed with water and saturated brine in order, dried over anhydrous magnesium sulfate and concentrated in vacuo. The resultant residue was chromatographed on a column of silica gel, eluting with ethyl acetate and hexane (1:3) to (1:1) to give 1.71 g of the titled compound.

Provenance & Evidence