Реакция #5987

Уравнение реакции

water

4-Chloropyridine hydrochloride

5-amino-1-methylindole

sodium carbonate

4-chloropyridine hydrochloride

→

solid

Выход 53.3%

1-Methyl-5-(4-pyridinylamino)-1H-indole

Выход 53.3%

Растворители

1-methyl-2-pyrrolidinone

Условия реакции

Обработка

1. 1
   Другоеpreheated to 100° C
2. 2
   Другоеno further reaction
3. 3
   ТемператураAfter two hours the reaction mixture was cooled
4. 4
   Экстракцияextracted with ethyl acetate
5. 5
   СушкаThe dried (anhydrous magnesium sulfate) organic layer
6. 6
   Фильтрацияwas filtered
7. 7
   Другоеevaporated to 12.7 g of an oil
8. 8
   ПромывкаThe oil was eluted through silica with 10% methanol in dichloromethane via flash column chromatography
9. 9
   Другоеto give the product which
10. 10
    Другоеwas triturated with ether

Методика

4-Chloropyridine hydrochloride (8 g) was added to a solution of 5-amino-1-methylindole (7 g) in 75 ml 1-methyl-2-pyrrolidinone preheated to 100° C. The addition of 4-chloropyridine hydrochloride (4 g) after one hour caused no further reaction as determined by TLC. After two hours the reaction mixture was cooled, stirred with water, basified with sodium carbonate and extracted with ethyl acetate. The dried (anhydrous magnesium sulfate) organic layer was filtered and evaporated to 12.7 g of an oil. The oil was eluted through silica with 10% methanol in dichloromethane via flash column chromatography to give the product which was triturated with ether to yield 5.7 g of a solid, m.p. 202°-203° C. Recrystallization from acetonitrile yielded 5 g of product as crystals, mp 209°-211° C.

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