Potassium Bromide → HCID 72187942, compound

Participants

Reaction Steps

A solution of trifluoro-methanesulfonic acid [2-[(4-fluorophenyl)-methyl-carbamoyl]-3-methyl-5-morpholin-4-yl-phenyl]ester (synthesized according to the methods described in sections a) to d) of example 17) (0.16 g, 0.34 mmol), potassium fluoride (0.08 g, 1.41 mmol), potassium bromide (0.05 g, 0.40 mmol) and cyclopropylboronic acid (0.06 g, 0.67 mmol) in dry toluene (3 ml) is degassed and flushed with argon for 20 min. To the reaction mixture is added tetrakis(triphenylphosphin)palladium(0) (0.039 g, 0.033 mmol) and subjected to microwave irradiation at 120° C. for 1 h. The reaction mixture is poured onto ice and extracted with ethyl acetate (3×30 ml). The combined organic layers are washed with water (20 ml), brine (20 ml) and dried over sodium sulfate. The solvent is evaporated to get the crude product. The reaction is repeated once and the combined fractions are purified by column chromatography (silica gel, 20% ethyl acetate/hexane) followed by preparative HPLC to afford N-[(4-fluorophenyl)-methyl]-2-cyclopropyl-6-methyl-4-morpholin-4-yl-benzamide (example 18) (0.12 g, 0.32 mmol, 28%). [M+H]+ 369.2.

Provenance & Evidence