反応 #5987

反応方程式

water

4-Chloropyridine hydrochloride

5-amino-1-methylindole

sodium carbonate

4-chloropyridine hydrochloride

→

solid

収率 53.3%

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

収率 53.3%

溶媒

1-methyl-2-pyrrolidinone

反応条件

後処理

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

実験手順

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.

出典