Water → 2,2-Dimethyl-N-[4-methyl-2-[6-(trifluoromethyl)-2-pyrazinyl]phenyl]propanamide

Participants

Reaction Steps

The product obtained from Step B (0.8 g, 2.3 mmol) was dissolved in N-methylpyrrolidinone (16 mL). Cuprous iodide (1.7 g, 9.2 mmol) and sodium trifluoroacetate (2.5 g, 18.4 mmol) were then added and the resultant mixture heated at 180° C. for 6 h. After cooling to room temperature, diethyl ether (200 mL) and water (100 mL) were added. The two-phase mixture was filtered through a pad of Celite and the filter cake subsequently washed with three 50 mL-portions of ether. The layers of the filtrate were separated and the ether layer dried (MgSO4). The ethereal solution was evaporated and the residue chromatographed on silica gel eluting with 15% ethyl acetate/hexane. In this manner, 0.14 g (18%) of the title compound was obtained as a yellow semisolid. 1H NMR (300 MHz,CDCl3) δ 10.25 (br s,1H), 9.18 (s,1H), 8.93 (s,1H), 8.33-8.35 (m,1H), 7.41 (s, 1H), 7.33-7.35 (m,1H), 2.41 (s,3H), 1.25 (s,9H). 19F NMR (282 MHz, CDCl3) δ 67.2.

Provenance & Evidence