4-Fluoroaniline → N-(4-Fluorophenyl)-6-[3-(trifluoromethyl)phenoxy]pyrazine-2-carboxamide

Participants

Reaction Steps

Analogously to Example 3, 25 mmol of 2-chloro-6-[3-(trifluoromethyl)phenoxy]pyrazine (prepared according to U.S. Pat. No. 4,254,125, Example 21), 27.5 mmol of 4-fluoroaniline, 2.92 g (27.5 mmol) of sodium carbonate, 17.5 mg (25 μmol) of dichlorobis(triphenylphosphine)-palladium(II) and 0.31 g (0.75 mmol) of (±)-1-[2-(diphenylphosphino)-ferrocenyl]ethyl-di-tert-butylphosphine in 25 ml of xylene were reacted under a CO pressure of 17 bar at 120° C. for 21 hours. The composition of the dissolved products in the xylene phase was determined by GC. 65.3 percent of the title compound (amide) and 34.7 percent of by-product (secondary amine) were found. The amide was isolated by column chromatography and purified. Data concerning the title product was:

Provenance & Evidence