Ethanol → HCID 178472613, compound

HRID 599499Notes

Reaction equation

HRID 599499 reaction equation
[Br:1][CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].N1([CH:13]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[NH:15][C:14]2=C)CCCC1.[CH3:23][CH2:24]O>>[Br-:1].[CH2:6]([O:5][C:3]([CH2:2][N+:15]1[C:16]2[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:13](=[CH:16][N:15]2[CH2:24][CH2:23][CH2:13][CH2:14]2)[CH:14]=1)=[O:4])[CH3:7]

Participants

4

Reactant 3

HCID 702EthanolHCID 7748Ethyl bromoacetateHCID 67273798HCID 67273798, compound

Product 1

HCID 178472613HCID 178472613, compoundYield 93%

Procedure

Ethyl bromoacetate (6.1 ml, 55.4 mmol) was added dropwise to a stirred solution of 3-pyrrolidin-1-yl-methylene-3H-indole (10 g, 50.4 mmol) in EtOH (40 ml) and the reaction mixture was kept stirring at rt overnight. The solid was filtered off, washed with small portions of EtOH and then dried in vacuo, affording title compound (17 g) as a beige solid in 93% yield. tR (LC-1): 1.45 min; ESI-MS(+): m/z 285.31 [M]+ (calcd 285.36 for C17H21BrN2O2+).

Workup

  1. filtrationThe solid was filtered off
  2. washwashed with small portions of EtOH
  3. customdried in vacuo

Sources & evidence

ORD record
ord-4bcdf381a6d541c8a8624bece6de8ba3
Source dataset
uspto-grants-2011_03
Patent number
US07897788B2

Reaction notes

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