Dimethylformamide → 3-{1-[(Diphenylmethyl)azetidin-3-yl]-2-fluoro-2-methylpropyl}-5-fluorobenzonitrile

Participants

Reaction Conditions

Reaction Steps

A solution of 16.19 g (34.42 mmol) of 3-[1-(3-bromo-5-fluorophenyl)-2-fluoro-2-methylpropyl]-1-(diphenylmethyl)azetidine, 3.23 g (27.53 mmol) of zinc cyanide, 1.10 g (1.2 mmol) of tris(dibenzylideneacetone)dipalladium, and 1.53 g (2.75 mmol) of DPPF in 99 mL of DMF and 1 mL of water was degassed for 1 h at rt. Then it was stirred at 140° C. After 17 h, it was concentrated to remove solvents. Then the mixture was poured into 300 mL of ether/ethyl acetate (1:1) and 100 mL aq NaHCO3. The organic layer was dried over Na2SO4 and concentrated. The residue was purified by silica gel chromatography with hexanes/ethyl acetate to afford the title compound as a white solid; 1H-NMR(CDCl3) δ 1.22(d, 3H, J=21 Hz), 1.30(d, 6H, J=21 Hz), 2.30 (t, 1H, J=7.8 Hz), 2.86-2.96 (m, 2H), 3.08-3.18 (m, 2H), 3.65 (t, 1H, J=7 Hz), 4.25 (s, 1H), 7.13-7.43 (m, 13H); Mass Spectrum: m/e=417 (M+1).

Provenance & Evidence