Diethyl (ethoxymethylene)malonate → 10-bromo-5-ethoxycarbonyl-2-methoxy-4H-pyrido [3,2,1-jk]carbazole-4-one

HRID 1530981Notes

Reaction equation

HRID 1530981 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:6][C:7]3[C:12]([C:13]=2[CH:14]=1)=[CH:11][C:10]([O:15][CH3:16])=[CH:9][CH:8]=3.C([O:19][CH:20]=[C:21]([C:27](OCC)=O)[C:22]([O:24][CH2:25][CH3:26])=[O:23])C>C1(C)C(C)=CC=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]3[CH:27]=[C:21]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[C:20](=[O:19])[C:8]4[CH:9]=[C:10]([O:15][CH3:16])[CH:11]=[C:12]([C:13]=2[CH:14]=1)[C:7]3=4

Participants

4

Reactant 2

HCID 6871Diethyl (ethoxymethylene)malonateHCID 15886922HCID 15886922, compound

Product 1

HCID 2125285710-bromo-5-ethoxycarbonyl-2-methoxy-4H-pyrido [3,2,1-jk]carbazole-4-oneYield 50%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

3-bromo-6-methoxycarbazole (2.5 g) produced in Example 1, step 1 and diethyl ethoxymethylenemalonate (9.16 ml) were dissolved in xylene, and the solution was heated under reflux in an argon atmosphere for 120 hours, and allowed to cool. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (eluent: chloroform) to obtain the title compound (2 g, 50%).

Workup

  1. temperaturethe solution was heated
  2. temperatureunder reflux in an argon atmosphere for 120 hours
  3. temperatureto cool
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (eluent: chloroform)

Sources & evidence

ORD record
ord-789a2fc874384b20a9791083ef833f30
Source dataset
uspto-grants-2001_03
Patent number
US06197768B1

Reaction notes

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