Aniline → HCID 57833590, compound

Participants

Reaction Conditions

Reaction Steps

A solution of trifluoromethanesulfonic acid 9-[8-(2,2,2-trifluoroacetyl)-8-aza-bicyclo[3.2.1]oct-3-ylidene]-9H-xanthen-4-yl ester in toluene (0.1 to 2 M solution) may be treated with a catalytic amount of a palladium catalyst such as Pd2(dba)3 (0.01 to 0.1 equiv), DPPF (0.1 to 0.3 equiv), aniline (2 to 5 equiv), sodium tert-butoxide (1.2 to 2 equiv) under an argon atmosphere. The mixture may be heated to 80° C. for a period of 1 to 10 hr. After filtration and removal of the solvent via evaporation, the residue may be taken up in a halogenated solvent such as methylene chloride, and the solution may be washed with water, dried over a suitable drying agent such as magnesium sulfate, filtered, and concentrated. The residue may be purified via column chromatography to yield Compound 1d.

Provenance & Evidence