Reaction #84203

Reaction equation

sodium hydride

1-bromopentane

5-methoxy-3-(1-naphthoyl)-1H-indole

→

title compound 5

5-methoxy-3-(1-naphthoyl)-N-pentyl-1H-indole

Solvents

DMF

DMF

DMF

Conditions

Workup

1. 1
   TemperatureThe solution was then cooled to room temperature and to this mixture
2. 2
   workup.STIRRINGThe mixture was stirred at 60° C. for 1 h
3. 3
   OtherThe solvent was removed under high vacuum
4. 4
   Extractionextracted by ethyl acetate (2×200 ml)
5. 5
   WashThe combined ethyl acetate phases were washed by water (1×100 ml), brine (1×100 ml)
6. 6
   Dryingdried over sodium sulphate
7. 7
   Filtrationfiltered
8. 8
   Concentrationconcentrated to dryness
9. 9
   OtherThe crude product obtained
10. 10
    Otherwas purified by chromatography on silica gel

Procedure

To a suspension of sodium hydride (1.54 g, 45 7 mmol, 60% in mineral oil) in DMF (100 ml) under nitrogen was added dropwise a solution of 5-methoxy-3-(1-naphthoyl)-1H-indole 4 (9.83 g, 32.6 mmol) in DMF (50 ml) and the mixture was stirred at 40° C. for 1 h. The solution was then cooled to room temperature and to this mixture was added a solution of 1-bromopentane (8.2 g, 54.3 mmol) in DMF (25 ml). The mixture was stirred at 60° C. for 1 h. The solvent was removed under high vacuum and the crude product was suspended in water (200 ml) and extracted by ethyl acetate (2×200 ml). The combined ethyl acetate phases were washed by water (1×100 ml), brine (1×100 ml), dried over sodium sulphate, filtered and concentrated to dryness. The crude product obtained was purified by chromatography on silica gel using hexane/ethyl acetate (7/3) to give the title compound 5 as an oil which solidified upon cooling (7.1 g, 59%).

Source