Reaktion #219788

Reaktionsgleichung

5-Amino-6-(2-tert-butylphenoxy)nicotinonitrile

copper (1) cyanide

dioxane

→

solid

1-(2-(2-tert-Butylphenoxy)-5-cyanopyridin-3-yl)-3-(4-tert-butylphenyl)urea

Lösungsmittel

ether

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe mixture was cooled to rt
2. 2
   Filtrationfiltered through Celite® and silica (3 g)
3. 3
   Einengenconcentrated

Vorschrift

5-Amino-6-(2-tert-butylphenoxy)nicotinonitrile: A mixture of 63c (676 mg, 2.1 mmol), copper (1) cyanide (755 mg, 8.4 mmol), tris(dibenzilideneacetone)dipalladium(0) (77 mg, 0.08 mmol), bis(diphenylphosphino)ferrocene (187 mg, 0.34 mmol) and tetraethylammonium cyanide (330 mg, 2.1 mmol) in dioxane (11 mL) was heated at 105° C. overnight. The mixture was cooled to rt, diluted with ether (50 mL), filtered through Celite® and silica (3 g) and concentrated to give a brown solid (883 mg). The solid was purified by SiO2 chromatography (40 g) to afford 63d (472 mg. 84% yield) as a yellow solid; HPLC purity 95%, 3.37 min (Method A); [M+H]+=268.15; 1H NMR (CDCl3) δ ppm: 1.35 (s, 9 H) 4.26 (s, 2 H) 6.95 (d, J=7.70 Hz, 1 H) 7.15 (s, 1 H) 7.20 (t, J=7.70 Hz, 1 H) 7.25 (t, J=7.42 Hz, 1 H) 7.47 (d, J=7.70 Hz, 1 H) 7.82 (s, 1 H); 13C NMR (CDCl3) δ ppm: 154.22, 151.27, 141.40, 139.75, 131.98, 127.57, 127.03, 125.53, 123.53, 121.69, 117.38, 104.08, 34.60, 30.47.

Quelle