Реакция #81467

ord-ec36e245e4bc42cbbd4e9cfcb89b3272

Уравнение реакции

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

Реактанты

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

Реагенты

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

Растворители

C1CCOC1
THF

Условия реакции

Температура
80°CELSIUS
Подробные условия
See reaction.notes.procedure_details.

Обработка

  1. 1
    Температураthe mixture heated
  2. 2
    Температураto cool

Методика

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.

Источник

DOI: 10.6084/m9.figshare.5104873.v1Патент: US05618807uspto-grants-1997_04