Dimethylformamide → HCID 68849508, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 729 mg (1.97 mmol) of tert-butyl 3-(5-trifluoromethylsulfonyloxy-6-methylpyridin-2-yl)propanoate (from Step E) and 464 mg (3.95 mmol) of zinc cyanide in 10 mL of DMF was added 137 mg (0.12 mmol) of tetrakis(triphenylphosphine)palladium(0). After stirring at 85° C. for 4 h, the reaction mixture was diluted with 10 mL of EtOAc and filtered through a cake of Celite. Solid was washed with EtOAc (3×10 mL) and the filtrate was concentrated. Chromatography on a Biotage 40M cartridge using 3:17 v/v EtOAc/hexanes as the eluant afforded 487 mg of the title compound: 1H NMR (500 MHz, CDCl3) δ 1.42 (s, 9H), 2.71 (d, J=7.4, 2H), 2.73 (s, 3H), 3.09 (d, J=7.3, 2H), 7.12 (d, J=8.0, 1H), 7.77 (d, J=8.0, 1H).

Provenance & Evidence