Reacción #5988

Ecuación de reacción

methyl chloroformate

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

→

solid

Rendimiento 98.4%

N-(1-Methyl-1H-indol-5-yl)-N-(4-pyridinyl) carbamic acid methyl ester

Rendimiento 98.4%

Disolventes

DCM

DCM

triethylamine

Condiciones de reacción

Tratamiento posterior

1. 1
   Lavadowas washed with water and saturated sodium chloride
2. 2
   Secadodried (anhydrous magnesium sulfate)
3. 3
   Filtraciónfiltered
4. 4
   Otroevaporated to 4 g of a solid
5. 5
   LavadoElution through silica with 50% ethyl acetate in dichloromethane via flash column chromatography

Procedimiento

A solution of methyl chloroformate (1.3 g) in 5 ml DCM was added to a solution of 1-methyl-5-(4-pyridinylamino)-1H-indole (2.5 g) in 120 ml DCM and 6 ml triethylamine (4.4 g). After stirring one hour at ambient temperature the reaction mixture was washed with water and saturated sodium chloride, dried (anhydrous magnesium sulfate), filtered and evaporated to 4 g of a solid. Elution through silica with 50% ethyl acetate in dichloromethane via flash column chromatography yielded 3.1 g of a solid. Recrystallization from methanol yielded 2.4 g of crystals, mp 157°-159° C.

Fuente