1,8-Diazabicyclo(5.4.0)undec-7-ene → 8,9-dihydro-7-[(5-methyl-1-trityl-1H-imidazol-4-yl)methylene]pyrido[1,2-a]indol-6(7H)-one

HRID 847501Notes

Reaction equation

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

Participants

Conditions

Temperature: 55 °C

Procedure

To a solution of 7-[(acetoxy)(5-methyl-1-trityl-1H-imidazol-4-yl)methyl]-8,9-dihydropyrido[1,2-a]indol-6(7H)-one in toluene (30 ml) at room temperature was added 1,8-diazabicyclo[5.4.0]undec-7-ene (762 mg). After being stirred at 55° C. for 2 hours, the solution was evaporated in vacuo. The residue was diluted with chloroform, washed with water, and dried over anhydrous magnesium sulfate. After evaporation of the solvent, the residue obtained was purified with silica gel column chromatography (eluent:chloroform) to give 8,9-dihydro-7-[(5-methyl-1-trityl-1H-imidazol-4-yl)methylene]pyrido[1,2-a]indol-6(7H)-one (1.3 g).

Workup

customthe solution was evaporated in vacuo
additionThe residue was diluted with chloroform
washwashed with water
dry with materialdried over anhydrous magnesium sulfate
customAfter evaporation of the solvent
customthe residue obtained
customwas purified with silica gel column chromatography (eluent:chloroform)

Sources & evidence

ORD record: ord-b2dabf4fc3b54e5685ba91c18476151b
Source dataset: uspto-grants-1992_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05141945

Reaction notes

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