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 486194Notes

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-569bcac996cd4ecfb9320ac7f57bd83e
Source dataset: uspto-grants-1994_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05290785

Reaction notes

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