تفاعل #81459

معادلة التفاعل

diethyl(3-pyridyl)borane

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

sodium carbonate

→

title compound

المردود 84.0%

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

المردود 84.0%

المذيبات

THF

ظروف التفاعل

المعالجة

1. 1
   غسيلChromatography, on elution with dichloromethane

الإجراء التجريبي

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+).

المصدر