반응 #49836

반응 방정식

water

4-Chloropyridine hydrochloride

5-amino-1-methylindole

sodium carbonate

4-chloropyridine hydrochloride

→

solid

수율 53.3%

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

수율 53.3%

용매

1-methyl-2-pyrrolidinone

반응 조건

후처리

1. 1
   기타preheated to 100° C
2. 2
   기타no further reaction
3. 3
   온도After two hours the reaction mixture was cooled
4. 4
   추출extracted with ethyl acetate
5. 5
   건조The dried (anhydrous magnesium sulfate) organic layer
6. 6
   여과was filtered
7. 7
   기타evaporated to 12.7 g of an oil
8. 8
   세척The oil was eluted through silica with 10% methanol in dichloromethane via flash column chromatography
9. 9
   기타to give the product which
10. 10
    기타was triturated with ether

실험 절차

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.

출처