Reacción #81459

Ecuación de reacción

diethyl(3-pyridyl)borane

androsta-3,5,16-trien-17-yl trifluoromethanesulphonate

sodium carbonate

→

title compound

Rendimiento 84.0%

17-(3-Pyridyl)androsta-3,5,16-triene

Rendimiento 84.0%

Disolventes

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   LavadoChromatography, on elution with dichloromethane

Procedimiento

The method followed that described in Example 1, using in step (b) diethyl(3-pyridyl)borane (0.88g, 6.0 mmol), androsta-3,5,16-trien-17-yl trifluoromethanesulphonate (2.01g, 5.0 mmol), prepared in step (a), THF (25 ml), bis(triphenylphosphine)palladium(II) chloride (35 mg, 0.05 mmol), and aqueous sodium carbonate (2M, 10 ml). Chromatography, on elution with dichloromethane, afforded the title compound (1.39 g, 84%) which crystallised from hexane, m.p. 110°-112° C. 1H-NMR (CDCl3) inter alia δ 1.02(3H,s,19-CH3), 1.07(3H,s,18-CH3), 5.44(1H,m,6-H), 5.61(1H,m,3-H), 5.95(1H,dm, J 9.8 Hz, 4-H), 6.01(1H,m, 16-H), 7.23(1H,m,Py 5-H), 7.66(1H,m,Py 4-H), 8.46(1H,m,Py 6-hr), 8.63(1H,m,Py 2-H); MS m/z 331 (M+).

Fuente