Reaction #81459

ord-4a2ce9feb87d4d10bdd8e66b84826df9

Reaction equation

CCB(CC)c1cccnc1
diethyl(3-pyridyl)borane
C[C@]12CCC=CC1=CC[C@@H]1[C@@H]2CC[C@]2(C)C(OS(=O)(=O)C(F)(F)F)=CC[C@@H]12
androsta-3,5,16-trien-17-yl trifluoromethanesulphonate
O=C([O-])[O-].[Na+].[Na+]
sodium carbonate
→
C[C@]12CCC=CC1=CC[C@@H]1[C@@H]2CC[C@]2(C)C(c3cccnc3)=CC[C@@H]12
title compound
Yield 84.0%
C[C@]12CCC=CC1=CC[C@@H]1[C@@H]2CC[C@]2(C)C(c3cccnc3)=CC[C@@H]12
17-(3-Pyridyl)androsta-3,5,16-triene
Yield 84.0%

Reactants

CCB(CC)c1cccnc1
diethyl(3-pyridyl)borane
C[C@]12CCC=CC1=CC[C@@H]1[C@@H]2CC[C@]2(C)C(OS(=O)(=O)C(F)(F)F)=CC[C@@H]12
androsta-3,5,16-trien-17-yl trifluoromethanesulphonate
O=C([O-])[O-].[Na+].[Na+]
sodium carbonate

Reagents

[Cl][Pd]([Cl])([P](c1ccccc1)(c1ccccc1)c1ccccc1)[P](c1ccccc1)(c1ccccc1)c1ccccc1
bis(triphenylphosphine)palladium(II) chloride

Solvents

C1CCOC1
THF

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    WashChromatography, on elution with dichloromethane

Procedure

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+).

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05618807uspto-grants-1997_04