Pyrrolidine → 5-(3-oxo-3-pyrrolidin-1-yl-propyl)-1H-indole-2-carboxylic acid ethyl ester

HRID 49058Notes

Reaction equation

HRID 49058 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]([CH2:15][CH2:16][C:17]([OH:19])=O)=[CH:10][CH:9]=2)=[O:5])[CH3:2].C(N1C=CN=C1)(N1C=CN=C1)=O.[NH:32]1[CH2:36][CH2:35][CH2:34][CH2:33]1>CN(C)C=O.ClCCl>[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([CH2:15][CH2:16][C:17](=[O:19])[N:32]1[CH2:36][CH2:35][CH2:34][CH2:33]1)=[CH:10][CH:9]=2)=[O:5])[CH3:2]

Participants

6

Reactant 3

HCID 31268PyrrolidineHCID 682631,1'-CarbonyldiimidazoleHCID 695870585-(2-carboxy-ethyl)-1H-indole-2-carboxylic acid ethyl ester

Product 1

HCID 695868775-(3-oxo-3-pyrrolidin-1-yl-propyl)-1H-indole-2-carboxylic acid ethyl esterYield 95.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-(2-carboxy-ethyl)-1H-indole-2-carboxylic acid ethyl ester (1.3 g, 5 mmol) in 10 mL of dimethylformamide, was added 1,1′-carbonyldiimidazole (973 mg, 6 mmol). The mixture was stirred under nitrogen at room temperature for 30 mins. To the reaction mixture was added pyrrolidine (1.3 mL, 15 mmol) dropwise. After stirring at room temperature for overnight, the reaction was diluted with dichloromethane (300 mL), washed with 1N hydrochloric acid, saturated sodium bicarbonate solution, brine, dried and concentrated to give 1.5 g (95%) of 5-(3-oxo-3-pyrrolidin-1-yl-propyl)-1H-indole-2-carboxylic acid ethyl ester.

Workup

  1. stirringAfter stirring at room temperature for overnight
  2. washwashed with 1N hydrochloric acid, saturated sodium bicarbonate solution, brine
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-0a54a77a82ee43f99027cffc5825b398
Source dataset
uspto-grants-2004_03
Patent number
US06706709B2

Reaction notes

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