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

HRID 41026Notes

Reaction equation

HRID 41026 reaction equation
CO[C:3]([C:5]1([CH3:28])[CH2:17][C:16]2[C:15]3[C:10](=[CH:11][CH:12]=[C:13]([O:18][CH2:19][CH3:20])[CH:14]=3)[NH:9][C:8]=2[CH:7]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([OH:27])[CH:22]=2)[NH:6]1)=[O:4].[Br:29][CH2:30][CH2:31][N:32]=[C:33]=[O:34]>CC(=O)CC>[Br:29][CH2:30][CH2:31][N:32]1[C:33](=[O:34])[N:6]2[CH:7]([C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([OH:27])[CH:22]=3)[C:8]3[NH:9][C:10]4[C:15]([C:16]=3[CH2:17][C:5]2([CH3:28])[C:3]1=[O:4])=[CH:14][C:13]([O:18][CH2:19][CH3:20])=[CH:12][CH:11]=4

Participants

4

Reactant 2

HCID 42559572-Bromoethyl isocyanateHCID 68886227(1RS,3SR)-1-(3-hydroxy-phenyl)-6-ethoxy-3-methyl-2,3,4,9-tetrahydro-1H-beta-carboline-3-carboxylic acid methyl ester

Product 1

HCID 68937590(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-dioneYield 40%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

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

Workup

  1. temperatureThe mixture is heated
  2. temperatureto reflux for 24 h
  3. customThe solvent is removed under reduced pressure
  4. customThe crude product is purified by column chromatography (silica gel; toluene, ethyl acetate 6:1)

Sources & evidence

ORD record
ord-90fd3c185f8b4a22bad918afbe59d1b6
Source dataset
uspto-grants-2013_09
Patent number
US08530493B2

Reaction notes

Loading…