Reacción #44913

Ecuación de reacción

sodium hydride

2-methyl-1H-indole-3-carboxylic acid ethyl ester

Benzyl bromide

→

1-benzyl-2-methyl-1H-indole-3-carboxylic acid, ethyl ester

Rendimiento 67.0%

ethyl 1-benzyl-2-methyl-1H-indole-3-carboxylate

Rendimiento 67.0%

Disolventes

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturato warm to room temperature
2. 2
   workup.STIRRINGstirred for 24 h
3. 3
   TemperaturaThe reaction was cooled to 0° C.
4. 4
   Otroquenched with water
5. 5
   Extracciónextracted with EtOAc
6. 6
   Lavadowashed with brine
7. 7
   Secadodried over Na2SO4
8. 8
   Concentraciónconcentrated under reduced pressure
9. 9
   OtroThe residue was purified by flash column chromatography on silica gel (40% EtOAc-hexanes)

Procedimiento

General Procedure 11.-To a mixture of sodium hydride (0.28 g, 60% in mineral oil, 0.17g, 7.0 mmol) in 10 ml of tetrahydrofuran stirring at 0° C. under argon, was added 2-methyl-1H-indole-3-carboxylic acid ethyl ester (1.17 g, 5.8 mmol) and the solution was stirred at 0° C. for 15 min. Benzyl bromide (0.80 ml, 1.15 g, 6.7 mmol) was then added and the reaction allowed to warm to room temperature and stirred for 24 h. The reaction was cooled to 0° C., quenched with water, extracted with EtOAc, washed with brine, dried over Na2SO4, and concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel (40% EtOAc-hexanes) to yield 1-benzyl-2-methyl-1H-indole-3-carboxylic acid, ethyl ester (Compound 57) as a tan solid (1.13 g, 67%).

Fuente