Sodium hydride → 5-(2-ethoxycarbonyl-5-benzyloxy-3-phenyl-1H-indole-1-yl)-valeric acid ethylester

HRID 66825

Reaction equation

HRID 66825 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:12][C:11]([O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[CH:10][CH:9]=2)=[O:5])[CH3:2].[H-].[Na+].[CH2:31]([O:33][C:34](=[O:40])[CH2:35][CH2:36][CH2:37][CH2:38]Br)[CH3:32]>CN(C)C=O>[CH2:31]([O:33][C:34](=[O:40])[CH2:35][CH2:36][CH2:37][CH2:38][N:7]1[C:8]2[C:13](=[CH:12][C:11]([O:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[CH:10][CH:9]=2)[C:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[C:6]1[C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH3:32]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 84580Ethyl 5-bromovalerateHCID 47778625-benzyloxy-3-phenyl-1H-2-indole-carboxylic acid ethylester

Product 1

HCID 542507335-(2-ethoxycarbonyl-5-benzyloxy-3-phenyl-1H-indole-1-yl)-valeric acid ethylester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

An amount of 23.5 g (63.3 m mole) of 5-benzyloxy-3-phenyl-1H-2-indole-carboxylic acid ethylester in absolute dimethylformamide was mixed with 3.0 g (63.3 m mole) of 50% sodium hydride. After 30 minutes, 13.2 g (63.3 m mole) of 5-bromo-valeric acid ethylester were added, and the mixture was stirred for three days. After evaporation, the residue obtained was chromatographed on silicagel (solvent: toluene/acetone (20.1)).

Workup

  1. customAfter evaporation
  2. customthe residue obtained
  3. customwas chromatographed on silicagel (solvent: toluene/acetone (20.1))

Sources & evidence

ORD record
ord-2380d4f359754994b05163591b874988
Source dataset
uspto-grants-1982_08
Patent number
US04343811

Linked notes

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