Reacción #84207

Ecuación de reacción

1-bromopentane

Indole 3-carboxylic acid

sodium hydride

→

title compound

Rendimiento 49.0%

3-carboxy-1-pentyl-1H-indole

Rendimiento 49.0%

Disolventes

DMF

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGThe mixture was stirred at room temperature overnight
2. 2
   OtroThe solvents were removed in vacuo and to the residue
3. 3
   workup.ADDITIONwas added water (30 ml) and ethyl acetate (30 ml)
4. 4
   OtroThe ethyl acetate portion was separated
5. 5
   Secadodried over sodium sulphate
6. 6
   Filtraciónfiltered
7. 7
   Otroevaporated to dryness
8. 8
   OtroThe crude residue was purified by column chromatography (silica gel: 20% ethyl acetate in hexane)

Procedimiento

Indole 3-carboxylic acid (3 g, 18.62 mmol) was added to a suspension of sodium hydride (60% in oil) (1.11 g, 1.5 eq) in dry DMF (30 ml) under a nitrogen atmosphere. The mixture was stirred at room temperature for 45 min (H2 evolving has ceased) and to this was added 1-bromopentane (4.62 ml, 2 eq) in dry DMF (10 ml) dropwise. The mixture was stirred at room temperature overnight. The solvents were removed in vacuo and to the residue was added water (30 ml) and ethyl acetate (30 ml). The ethyl acetate portion was separated, dried over sodium sulphate, filtered and evaporated to dryness. The crude residue was purified by column chromatography (silica gel: 20% ethyl acetate in hexane) to give the title compound (2.12 g, 49%) as a cream solid.

Fuente