Sodium hydride → N-(5-Ethoxycarbonylpentyl)-3-(1-naphthoyl)-1H-indole

HRID 55922

Reaction equation

HRID 55922 reaction equation
[H-].[Na+].[C:3]1([C:13]([C:15]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[NH:17][CH:16]=2)=[O:14])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=1.Br[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31]>CN(C=O)C>[CH2:33]([O:32][C:30]([CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][N:17]1[C:18]2[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:15]([C:13]([C:3]2[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[CH:6]=[CH:5][CH:4]=2)=[O:14])=[CH:16]1)=[O:31])[CH3:34]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 117544Ethyl 6-bromohexanoateHCID 103558253-Naphthoylindole

Product 1

HCID 68159362N-(5-Ethoxycarbonylpentyl)-3-(1-naphthoyl)-1H-indole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of sodium hydride (1.1 g, 30 mmol, 60% in mineral oil) in DMF (100 ml) under nitrogen was added solid 3-(1-naphthoyl)-1H-indole 1 (5.43 g, 20 mmol). After stirring at room temperature for 1 h, a solution of ethyl 6-bromohexanoate (6.6 g, 30 mmol) in DMF (10 ml) was added slowly with stirring over a period of 15 min and the mixture was then heated at 60° C. for 3 h. The solvent was removed under high vacuum and the crude product was suspended in water (150 ml) and extracted by ethyl acetate (2×150 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 (8/2) to give the title compound 2 as an oil which became solid in the cold (7.1 g, 86%).

Workup

  1. stirringwith stirring over a period of 15 min
  2. temperaturethe mixture was then heated at 60° C. for 3 h
  3. customThe solvent was removed under high vacuum
  4. extractionextracted by ethyl acetate (2×150 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-f58b4648f40e4319b79e4983a18f7599
Source dataset
uspto-grants-2016_09
Patent number
US09434687B2

Linked notes

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