Reaktion #5987

Reaktionsgleichung

water

4-Chloropyridine hydrochloride

5-amino-1-methylindole

sodium carbonate

4-chloropyridine hydrochloride

→

solid

Ausbeute 53.3%

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

Ausbeute 53.3%

Lösungsmittel

1-methyl-2-pyrrolidinone

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigepreheated to 100° C
2. 2
   Sonstigeno further reaction
3. 3
   TemperaturAfter two hours the reaction mixture was cooled
4. 4
   Extraktionextracted with ethyl acetate
5. 5
   TrocknenThe dried (anhydrous magnesium sulfate) organic layer
6. 6
   Filtrationwas filtered
7. 7
   Sonstigeevaporated to 12.7 g of an oil
8. 8
   WaschenThe oil was eluted through silica with 10% methanol in dichloromethane via flash column chromatography
9. 9
   Sonstigeto give the product which
10. 10
    Sonstigewas triturated with ether

Vorschrift

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.

Quelle