Реакция #50922

Уравнение реакции

N-(4-iodo-6-thiomorpholin-4-yl-pyridin-3-yl)-2,2-dimethyl-propionamide

sodium carbonate

o-tolylboronic acid

→

title compound

2,2-Dimethyl-N-(6-thiomorpholin-4-yl-4-o-tolyl-pyridin-3-yl)-propionamide

Растворители

toluene

Условия реакции

Обработка

1. 1
   ТемператураAfter cooling to room temperature
2. 2
   Другоеthe aqueous phase was separated
3. 3
   Промывкаwashed twice with ethyl acetate
4. 4
   ПромывкаThe combined organic layers were washed with 50 ml brine
5. 5
   Сушкаdried (sodium sulfate)
6. 6
   Другоеevaporated
7. 7
   ДругоеPurification by flash-chromatography

Методика

A mixture of 4.05 g (10.0 mmol) N-(4-iodo-6-thiomorpholin-4-yl-pyridin-3-yl)-2,2-dimethyl-propionamide, 54 ml toluene, 16 ml 2 N sodium carbonate solution, 347 mg (0.3 mmol) tetrakis(triphenylphosphine)palladium(0), 67 mg (0.3 mmol) palladium(II) acetate and 1.50 g (11.0 mmol) o-tolylboronic acid was heated under argon at 80° C. for 18 h. After cooling to room temperature, the aqueous phase was separated and washed twice with ethyl acetate. The combined organic layers were washed with 50 ml brine, dried (sodium sulfate) and evaporated. Purification by flash-chromatography gave 3.57 g (quantitative) of the title compound as a light brown solid.

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