1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 54325121, compound

HRID 847513Notes

Reaction equation

HRID 847513 reaction equation
C(O[CH:5]([C:22]1[N:23]=[CH:24][N:25]([C:28]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:26]=1[CH3:27])[CH:6]1[C:20](=[O:21])[N:10]2[C:11]3[C:16]([C:17]([CH3:18])=[C:9]2[CH2:8][CH2:7]1)=[CH:15][C:14]([Cl:19])=[CH:13][CH:12]=3)(=O)C.N12CCCN=C1CCCCC2>C1(C)C=CC=CC=1>[Cl:19][C:14]1[CH:15]=[C:16]2[C:11](=[CH:12][CH:13]=1)[N:10]1[C:20](=[O:21])[C:6](=[CH:5][C:22]3[N:23]=[CH:24][N:25]([C:28]([C:41]4[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=4)([C:35]4[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=4)[C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)[C:26]=3[CH3:27])[CH2:7][CH2:8][C:9]1=[C:17]2[CH3:18]

Participants

4

Reactant 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 10349022HCID 10349022, compound

Product 1

HCID 54325121HCID 54325121, compoundYield 87.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 7-[(acetoxy)(5-methyl-1-trityl-1H-imidazol-4-yl)methyl]-2-chloro-8,9-dihydro-10-methylpyrido[1,2-a]indol-6(7H)-one (1.40 g) in toluene (15 ml) was added 1.8-diazabicyclo[5.4.0]undec-7-ene (0.37 ml), and the mixture was refluxed for 2 hours. After being cooled, the solution was washed with water and brine, dried over sodium sulfate, evaporated, and triturated in diisopropyl ether, to give 2-chloro-8,9-dihydro-10-methyl-7-[(5-methyl-1-trityl-1H-imidazol-4-yl)methylene]pyrido[1,2-a]indol-6(7H)-one (1.11 g).

Workup

  1. temperaturethe mixture was refluxed for 2 hours
  2. temperatureAfter being cooled
  3. washthe solution was washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated
  6. customtriturated in diisopropyl ether

Sources & evidence

ORD record
ord-c9c5d6c5a1434fccb0c148dc5b729076
Source dataset
uspto-grants-1992_08
Patent number
US05141945

Reaction notes

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