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

HRID 41028Notes

Reaction equation

HRID 41028 reaction equation
CO[C:3]([C:5]1([CH3:27])[CH2:17][C:16]2[C:15]3[C:10](=[CH:11][CH:12]=[C:13]([O:18][CH3:19])[CH:14]=3)[NH:9][C:8]=2[CH:7]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([OH:26])[CH:21]=2)[NH:6]1)=[O:4].[Br:28][CH2:29][CH2:30][N:31]=[C:32]=[O:33]>CC(=O)CC>[Br:28][CH2:29][CH2:30][N:31]1[C:32](=[O:33])[N:6]2[CH:7]([C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([OH:26])[CH:21]=3)[C:8]3[NH:9][C:10]4[C:15]([C:16]=3[CH2:17][C:5]2([CH3:27])[C:3]1=[O:4])=[CH:14][C:13]([O:18][CH3:19])=[CH:12][CH:11]=4

Participants

4

Reactant 2

HCID 42559572-Bromoethyl isocyanateHCID 68851536(1RS,3RS)-1-(3-hydroxy-phenyl)-6-methoxy-3-methyl-2,3,4,9-tetrahydro-1H-beta-carboline-3-carboxylic acid methyl ester

Product 1

HCID 68939448(+)-2-(2-Bromo-ethyl)-10-(3-hydroxy-phenyl)-6-methoxy-3a-methyl-3a,4,9,10-tetrahydro-2,9,10a-triaza-cyclopenta[b]fluorene-1,3-dioneYield 74%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

To a solution of 3.17 g (1RS,3SR)-1-(3-Hydroxy-phenyl)-6-methoxy-3-methyl-2,3,4,9-tetrahydro-1H-beta-carboline-3-carboxylic acid methyl ester in 35 ml 2-butanon are added 860 μl bromoethyl isocyanate. The mixture is heated to reflux for 7 h and is stirred at room temperature over night. The precipitated compound is filtered and washed with 2-butanon. 3.09 g (74%) of the title compound are obtained. m.p.: 299-302° C., MS: m/z (MH+)=484.0/486.0

Workup

  1. temperatureThe mixture is heated
  2. temperatureto reflux for 7 h
  3. filtrationThe precipitated compound is filtered
  4. washwashed with 2-butanon

Sources & evidence

ORD record
ord-dcdaf9d0806047769f4203c19cf4bf47
Source dataset
uspto-grants-2013_09
Patent number
US08530493B2

Reaction notes

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