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1,2-Dibromoethane → tert-Butyl 2-(6-(10-chloro-1-oxo-3,4-dihydropyrazino[1,2-a]indol-2(1H)-yl)-1H-indol-1-yl)acetate

HRID 453872
Notes
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Reaction equation

HRID 453872 reaction equation
[Cl:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4][C:3]=1[C:11]([NH:13][C:14]1[CH:22]=[C:21]2[C:17]([CH:18]=[CH:19][N:20]2[CH2:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])=[CH:16][CH:15]=1)=[O:12].Br[CH2:32][CH2:33]Br>CCCC[N+](CCCC)(CCCC)CCCC.[Br-].[OH-].[Na+].O>[Cl:1][C:2]1[C:10]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[N:4]2[CH2:32][CH2:33][N:13]([C:14]3[CH:22]=[C:21]4[C:17]([CH:18]=[CH:19][N:20]4[CH2:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])=[CH:16][CH:15]=3)[C:11](=[O:12])[C:3]=12
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 2

HCID 78391,2-DibromoethaneHCID 59473712tert-Butyl 2-(6-(3-chloro-1H-indole-2-carboxamido)-1H-indol-1-yl)acetate

Product 1

HCID 59473664tert-Butyl 2-(6-(10-chloro-1-oxo-3,4-dihydropyrazino[1,2-a]indol-2(1H)-yl)-1H-indol-1-yl)acetateYield 78%

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalyst
HCID 962
Water
Solvent
HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
25 °C

Procedure

tert-Butyl 2-(6-(3-chloro-1H-indole-2-carboxamido)-1H-indol-1-yl)acetate (1.41 mmol, 1.0 equiv.) and TBAB (1.41 mmol, 1.0 equiv.) were dissolved in 1 N NaOH (12 ml); 1,2-dibromoethane (14.18 mmol, 10.0 equiv.) was added, and the mixture was stirred for 12 h at 25° C. The reaction mixture was diluted with water (50 ml) and extracted with ethyl acetate (100 ml). The organic phase was washed with sat. NaCl solution (50 ml), dried over Na2SO4 and concentrated under reduced pressure, and the desired product was obtained by purification by column chromatography. Yield: 78%

Workup

  1. extractionextracted with ethyl acetate (100 ml)
  2. washThe organic phase was washed with sat. NaCl solution (50 ml)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e3de5654c4e847958138c57a53c09c3d
Source dataset
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08492559B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes