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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 453872Generated: October 30, 2026

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

https://huagongshe.com/reaction/453872

Reaction equation

Participants

RoleNameHCIDCharge
Reactant1,2-DibromoethaneHCID 7839—
Reactanttert-Butyl 2-(6-(3-chloro-1H-indole-2-carboxamido)-1H-indol-1-yl)acetateHCID 59473712—
CatalystTetrabutylammonium BromideHCID 74236—
SolventWaterHCID 962—
SolventSodium HydroxideHCID 14798—
Producttert-Butyl 2-(6-(10-chloro-1-oxo-3,4-dihydropyrazino[1,2-a]indol-2(1H)-yl)-1H-indol-1-yl)acetateHCID 5947366478%

Reaction Conditions

Temperature25 °C

Reaction Steps

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%

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08492559B2
Source datasetuspto-grants-2013_07
ORD IDord-e3de5654c4e847958138c57a53c09c3d
Source noteuspto-grants-2013_07