反应 #5987

反应方程式

water

4-Chloropyridine hydrochloride

5-amino-1-methylindole

sodium carbonate

4-chloropyridine hydrochloride

→

solid

收率 53.3%

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

收率 53.3%

溶剂

1-methyl-2-pyrrolidinone

反应条件

后处理

1. 1
   其他preheated to 100° C
2. 2
   其他no further reaction
3. 3
   温度After two hours the reaction mixture was cooled
4. 4
   萃取extracted with ethyl acetate
5. 5
   干燥The dried (anhydrous magnesium sulfate) organic layer
6. 6
   过滤was filtered
7. 7
   其他evaporated to 12.7 g of an oil
8. 8
   洗涤The oil was eluted through silica with 10% methanol in dichloromethane via flash column chromatography
9. 9
   其他to give the product which
10. 10
    其他was triturated with ether

实验过程

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.

来源