Morpholine → 5-(2-morpholin-4-yl-2-oxo-ethoxy)-1H-indole-2-carboxylic acid ethyl ester

HRID 49049Notes

Reaction equation

HRID 49049 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([O:15][CH2:16][C:17]([OH:19])=O)=[CH:10][CH:9]=2)=[O:5])[CH3:2].[NH:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1>CN(C)C=O>[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([O:15][CH2:16][C:17]([N:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1)=[O:19])=[CH:10][CH:9]=2)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 8083MorpholineHCID 695866655-carboxymethoxy-1H-indole-2-carboxylic acid ethyl ester

Product 1

HCID 695873915-(2-morpholin-4-yl-2-oxo-ethoxy)-1H-indole-2-carboxylic acid ethyl esterYield 85%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 5-carboxymethoxy-1H-indole-2-carboxylic acid ethyl ester (1.5 g, 5.7 mmol) and 1-1′-carbonyldiimidazole (1.11 g, 6.85 mmol) in dimethylformamide (15 mL) was stirred at room temperature for 30 mins. To the mixture was then added morpholine (1 mL) and the stirring was continued for overnight. The reaction was concentrated and the residue was dissolved in dichloromethane (200 mL), washed with 1N hydrochloric acid, saturated sodium bicarbonate and brine, dried and concentrated to give 1.6 g (85%) of 5-(2-morpholin-4-yl-2-oxo-ethoxy)-1H-indole-2-carboxylic acid ethyl ester.

Workup

  1. concentrationThe reaction was concentrated
  2. dissolutionthe residue was dissolved in dichloromethane (200 mL)
  3. washwashed with 1N hydrochloric acid, saturated sodium bicarbonate and brine
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-4ee306c7d3e14477a1a4513cc76254b0
Source dataset
uspto-grants-2004_03
Patent number
US06706709B2

Reaction notes

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