Ethyl Acetate → PF-514273

Participants

Reaction Steps

To a stirred solution of 1-(2-chloro-phenyl)-5-(4-chloro-phenyl)4-hydroxy-1H-pyrazole-3-carboxylic acid (2,2-difluoro-propyl)-(2-hydroxy-ethyl)-amide I-3d (10 g, 21 mmol), triphenyl phosphine (8.4 g, 31.5 mmol) in toluene (210 ml) was added 1,1′-(azodicarbonyl)dipiperidine (8.0 g, 31.5 mmol). After 18 hours, 20% ethyl acetate:hexanes (210 ml) was added, the mixture was stirred at ambient temperature for 1 hour and filtered. The filtrate was concentrated in vacuo and the resulting oil was chromatographed on silica gel (20–70% ethyl acetate:hexanes) to afford the title compound (2A-1) as a solid, 7.8 g. 1H NMR in CDCl3 (ppm) δ 7.53–7.50 (m, 1H), 7.38–7.33 (m, 3H), 7.24–7.21 (m, 2H), 7.16–7.13 (m, 2H), 4.45 (br s, 2H), 4.02 (t, 2H), 3.90 (br s, 2H), 1.69 (t, 3H); ms (LCMS) m/z=452.2 (M+1). Combustion analysis calculated for: C: 55.77%; H: 3.79%; N: 9.29%. Found: C: 55.69%; H: 3.52%; N: 9.13%.

Provenance & Evidence