Dimethylformamide → 5-[4-(Allyl-methyl-amino)-butoxy]-2,3-dihydro-indole-1-carboxylic acid 4-chloro-phenyl ester

HRID 49496Notes

Reaction equation

HRID 49496 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]([N:11]2[C:19]3[C:14](=[CH:15][C:16]([O:20][CH2:21][CH2:22][CH2:23][CH2:24]Br)=[CH:17][CH:18]=3)[CH2:13][CH2:12]2)=[O:10])=[CH:4][CH:3]=1.[CH2:26]([CH2:29][NH2:30])[CH:27]=C.[CH3:31]N(C=O)C>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]([N:11]2[C:19]3[C:14](=[CH:15][C:16]([O:20][CH2:21][CH2:22][CH2:23][CH2:24][N:30]([CH2:29][CH:26]=[CH2:27])[CH3:31])=[CH:17][CH:18]=3)[CH2:13][CH2:12]2)=[O:10])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 4437323-Buten-1-amineHCID 695153545-(4-Bromo-butoxy)-2,3-dihydro-indole-1-carboxylic acid 4-chloro-phenyl ester

Product 1

HCID 695149675-[4-(Allyl-methyl-amino)-butoxy]-2,3-dihydro-indole-1-carboxylic acid 4-chloro-phenyl esterYield 66%

Procedure

106 mg (0.25 mmol) 5-(4-Bromo-butoxy)-2,3-dihydro-indole-1-carboxylic acid 4-chloro-phenyl ester in 2 ml DMF were treated with 71 mg (1 mmol) N-allylmethylamine at 50° C. for 2 h. The mixture was concentrated and purified by column chromatography on silica gel with CH2Cl2/MeOH 19:1 to give 68 mg (66%) 5-[4-(Allyl-methyl-amino)-butoxy]-2,3-dihydro-indole-1-carboxylic acid 4-chloro-phenyl ester as colorless solid, MS: 415 (M+, 1Cl).

Workup

  1. concentrationThe mixture was concentrated
  2. custompurified by column chromatography on silica gel with CH2Cl2/MeOH 19:1

Sources & evidence

ORD record
ord-a5f8525a2c9d4664b06067adea614c79
Source dataset
uspto-grants-2004_03
Patent number
US06706751B2

Reaction notes

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