Ethyl 6-chloro-5-cyanonicotinate → Ethyl 5-cyano-6-isobutylnicotinate

Participants

Reaction Conditions

Reaction Steps

To a solution of 145 mg (0.69 mmol) of ethyl 6-chloro-5-cyanonicotinate (from Step B), 1.65 mL (0.83 mmol) of isobutylzinc bromide (0.5 M in THF), and 100 mL of 1-methyl-2-pyrrolidinone was added 18 mg (0.03 mmol) bis(tri-tert-butylphosphine)palladium(0). After stirring at 65° C. overnight, the reaction mixture was cooled to rt and filtered through a cake of Celite. The filtrate was concentrated. Chromatography on a Biotage 40S cartridge using 1:19 v/v EtOAc/hexanes as the eluant gave 75 mg of the title compound: 1H NMR (500 MHz, CDCl3) δ 0.99 (d, J=6.7, 6H), 1.43 (t, J=7.1, 3H), 2.27 (m, 1H), 2.99 (d, J=7.3, 2H), 4.45 (q, J=7.1, 2H), 8.50 (d, J=2.1, 1H), 9.28 (d, J=2.3, 1H).

Provenance & Evidence