1-(5-FLUORO-2-PYRIDINYL)-4-OXO-CYCLOHEXANECARBONITRILE synthesis

Yield:-

Reaction Conditions:

with sodium chloride in water;dimethyl sulfoxide at 160; for 1 h;Heating / reflux;

Steps:

24.b

(b) To a solution of ketoester prepared above (3.6 g, 13 mmol) in DMSO (45 mL) containing boiling chips, was added NaCl (0.25 g, 4.3 mmol) and H₂O (0.45 mL). The reaction was heated to 160° C. with a reflux condenser in place and stirred for 1 h. The reaction was diluted with H₂O (10×) and extracted with Et₂O (3×50 mL). The combined organic, were washed with brine, dried over MgSO₄, and removed in vacuo. Silica gel chromatography (gradient elution 15-85% EtOAc in hexanes) afforded the ketone. ¹H NMR (400 Hz, CDCl₃): δ 2.4-2.65 (m, 6H), 2.80-2.89 (m, 2H), 7.45-7.51 (m, 1H), 7.70 (dd, J==12, 4 Hz, 1H), 8.46 (d, J=2.7 Hz, 1H).

References:

US2007/299080,2007,A1 Location in patent:Page/Page column 67-68