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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 41026Generated: November 1, 2026

2-Bromoethyl isocyanate → (3aSR,10RS)-2-(2-Bromo-ethyl)-6-ethoxy-10-(3-hydroxy-phenyl)-3a-methyl-3a,4,9,10-tetrahydro-2,9,10a-triaza-cyclopenta[b]fluorene-1,3-dione

https://huagongshe.com/reaction/41026

Reaction equation

Participants

RoleNameHCIDCharge
Reactant2-Bromoethyl isocyanateHCID 4255957—
Reactant(1RS,3SR)-1-(3-hydroxy-phenyl)-6-ethoxy-3-methyl-2,3,4,9-tetrahydro-1H-beta-carboline-3-carboxylic acid methyl esterHCID 68886227—
SolventMethyl Ethyl KetoneHCID 6569—
Product(3aSR,10RS)-2-(2-Bromo-ethyl)-6-ethoxy-10-(3-hydroxy-phenyl)-3a-methyl-3a,4,9,10-tetrahydro-2,9,10a-triaza-cyclopenta[b]fluorene-1,3-dioneHCID 6893759040%

Reaction Steps

To a solution of 500 mg (1.31 mmol) (1RS,3SR)-6-Ethoxy-1-(3-hydroxy-phenyl)-3-methyl-2,3,4,9-tetrahydro-1H-beta-carboline-3-carboxylic acid methyl ester in 25 ml 2-butanon are added 120 μl (1.31 mmol) bromoethyl isocyanate. The mixture is heated to reflux for 24 h. The solvent is removed under reduced pressure. The crude product is purified by column chromatography (silica gel; toluene, ethyl acetate 6:1). 260 mg (40%) of the title compound are obtained as a colorless solid. m.p.: 250-252° C., MS: m/z (MH+)=498.1/500.0

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08530493B2
Source datasetuspto-grants-2013_09
ORD IDord-90fd3c185f8b4a22bad918afbe59d1b6
Source noteuspto-grants-2013_09