Reacción #5987

Ecuación de reacción

water

4-Chloropyridine hydrochloride

5-amino-1-methylindole

sodium carbonate

4-chloropyridine hydrochloride

→

solid

Rendimiento 53.3%

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

Rendimiento 53.3%

Disolventes

1-methyl-2-pyrrolidinone

Condiciones de reacción

Tratamiento posterior

1. 1
   Otropreheated to 100° C
2. 2
   Otrono further reaction
3. 3
   TemperaturaAfter two hours the reaction mixture was cooled
4. 4
   Extracciónextracted with ethyl acetate
5. 5
   SecadoThe dried (anhydrous magnesium sulfate) organic layer
6. 6
   Filtraciónwas filtered
7. 7
   Otroevaporated to 12.7 g of an oil
8. 8
   LavadoThe oil was eluted through silica with 10% methanol in dichloromethane via flash column chromatography
9. 9
   Otroto give the product which
10. 10
    Otrowas triturated with ether

Procedimiento

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.

Fuente