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

HRID 1399479Notes

Reaction equation

HRID 1399479 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][CH:9]=[C:8]2[C:14]([C:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=[CH:18][CH:17]=1)=[O:15].Br[CH2:27][CH2:28][CH2:29][CH2:30][CH3:31]>CN(C=O)C>[CH3:3][O:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[N:10]([CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[CH:9]=[C:8]2[C:14]([C:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=[CH:18][CH:17]=1)=[O:15]

Participants

5

Reactant 3

HCID 80571-BromopentaneHCID 24758Sodium hydrideHCID 681592875-methoxy-3-(1-naphthoyl)-1H-indole

Product 1

HCID 681592935-methoxy-3-(1-naphthoyl)-N-pentyl-1H-indole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Conditions

Temperature
40 °C

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%).

Workup

  1. temperatureThe solution was then cooled to room temperature and to this mixture
  2. stirringThe mixture was stirred at 60° C. for 1 h
  3. customThe solvent was removed under high vacuum
  4. extractionextracted by ethyl acetate (2×200 ml)
  5. washThe combined ethyl acetate phases were washed by water (1×100 ml), brine (1×100 ml)
  6. dry with materialdried over sodium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated to dryness
  9. customThe crude product obtained
  10. customwas purified by chromatography on silica gel

Sources & evidence

ORD record
ord-fddd5e28b9b6410d99f92c9fbff5f6b4
Source dataset
uspto-grants-2014_12
Patent number
US08906633B2

Reaction notes

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