Reacción #1483076

Ecuación de reacción

3-(4-amino-phenylmethyl)-1-methyl-1H-indole-5-carboxylic acid methyl ester

DIPEA

benzoyl chloride

THF

→

3-(4-benzoylamino-phenylmethyl)-1-methyl-1H-indole-5-carboxylic acid methyl ester

Rendimiento 83.0%

Disolventes

ether

ethyl acetate

Condiciones de reacción

Tratamiento posterior

1. 1
   Lavadowashed with aq. NaHCO3 (50 mL)
2. 2
   SecadoThe organic layer was dried over MgSO4
3. 3
   Filtraciónfiltered
4. 4
   Concentraciónconcentrated

Procedimiento

A solution of 3-(4-amino-phenylmethyl)-1-methyl-1H-indole-5-carboxylic acid methyl ester (62 mg, 0.21 mmol), DIPEA (0.06 mL, 0.32 mmol), benzoyl chloride (0.03 mL, 0.23 mmol) and THF (5 mL) was stirred for 10 hr at room temperature. The solution was then diluted with ether (20 mL) and ethyl acetate (20 mL) and washed with aq. NaHCO3 (50 mL). The organic layer was dried over MgSO4, filtered and concentrated. The remaining residue was subjected to flash chromatography (ethyl acetate/hexane, 2:3) to provide 3-(4-benzoylamino-phenylmethyl)-1-methyl-1H-indole-5-carboxylic acid methyl ester (69 mg, 83% yield).

Fuente