Réaction #81467

ord-ec36e245e4bc42cbbd4e9cfcb89b3272

Équation de réaction

CCB(CC)c1cccnc1
Diethyl(3-pyridyl)borane
C[C@]12CC[C@H](O)CC1=CC[C@@H]1[C@@H]2CC[C@]2(C)C(I)=CC[C@@H]12
17-iodo-androsta-5,16-dien-3β-ol
O=C([O-])[O-].[Na+].[Na+]
sodium carbonate
→
C[C@]12CC[C@H](O)CC1=CC[C@@H]1[C@@H]2CC[C@]2(C)C(c3cccnc3)=CC[C@@H]12
17-(3-Pyridyl)androsta-5,16-dien-3β-ol

Réactifs

CCB(CC)c1cccnc1
Diethyl(3-pyridyl)borane
C[C@]12CC[C@H](O)CC1=CC[C@@H]1[C@@H]2CC[C@]2(C)C(I)=CC[C@@H]12
17-iodo-androsta-5,16-dien-3β-ol
O=C([O-])[O-].[Na+].[Na+]
sodium carbonate

Réactifs

[Cl][Pd][Cl].c1ccc(P(c2ccccc2)c2ccccc2)cc1.c1ccc(P(c2ccccc2)c2ccccc2)cc1
bis(triphenylphosphine)palladium (II) chloride

Solvants

C1CCOC1
THF

Conditions de réaction

Température
80°CELSIUS
Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    Températurethe mixture heated
  2. 2
    Températureto cool

Mode opératoire

Diethyl(3-pyridyl)borane (3.23 g, 22 mmol) from Aldrich Chemical Co. Ltd. was added to a stirred solution of 17-iodo-androsta-5,16-dien-3β-ol (7.96 g, 20 mmol) in THF (120 ml) containing bis(triphenylphosphine)palladium (II) chloride (140 mg, 0.2 mmol). An aqueous solution of sodium carbonate (2M, 50 ml) was then added and the mixture heated, with stirring, by an oil bath at 80° C. for 48 h, and allowed to cool.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US05618807uspto-grants-1997_04