Ethyl Acetate → 6-Cyano-2-(2-tertbutylphenoxy)pyridin-3-amine

Participants

Reaction Conditions

Reaction Steps

A mixture of 123a (1000 mg, 3.1 mmol), copper cyanide (1120 mg, 12.5 mmol), tris(dibenzylideneacetone)dipalladium(0) (114 mg, 0.12 mmol), 1,1′-Bis (diphenylphosphino) ferrocene (276 mg, 0.5 mmol) and tetraethylammonium cyanide (486 mg, 3.1 mmol) in dioxane (16 ml) was heated at 105° C. for 4.5 h. The reaction was completed as determined by TLC (30% ethyl acetate in heptane). The mixture was cooled to rt, diluted with ether (50 ml) filtered over Celite® and concentrated to give 1.3476 g of yellow foam. The foam was recrystallized from 30% ethyl acetate in heptane to give 123b (753.6 mg, 91% yield) as a brown powder. [M+H]+=268.13. 1H NMR (500 MHz, CDCl3) δ ppm 1.36 (s, 9H), 4.53 (s, 2H), 6.96 (dd, J=7.97, 4.12 Hz, 2H), 7.17 (t, J=7.42 Hz, 1H), 7.24 (m, 2H),7.44 (d, J=7.70 Hz, 1H).

Provenance & Evidence