1,8-Diazabicyclo(5.4.0)undec-7-ene → 10-ethyl-8,9-dihydro-7-[(5-methyl-1-trityl-1H-imidazol-4-yl)methylene]pyrido[1,2-a]indol-6(7H)-one

HRID 486212Notes

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

Participants

Conditions

Temperature: 75 °C

Procedure

To a solution of 7-[(acetoxy)(5-methyl-1-trityl-1H-imidazol-4-yl)methyl]-10-ethyl-8,9-dihydropyrido[1,2-a]indol-6(7H)-one (2.06 g) in toluene (30 ml) at room temperature was added 1,8-diazabicyclo[5.4.0]undec-7-ene (1.2 ml). After being stirred at 75° C. for 3 hours, the solution was diluted with chilled water. The organic layer separated was washed with aqueous oxalic acid solution, water, and brine, dried over anhydrous sodium sulfate, and evaporated in vacuo. The residue was triturated with methanol and filtered to give 10-ethyl-8,9-dihydro-7-[(5-methyl-1-trityl-1H-imidazol-4-yl)methylene]pyrido[1,2-a]indol-6(7H)-one (1.41 g).

Workup

customThe organic layer separated
washwas washed with aqueous oxalic acid solution, water, and brine
dry with materialdried over anhydrous sodium sulfate
customevaporated in vacuo
customThe residue was triturated with methanol
filtrationfiltered

Sources & evidence

ORD record: ord-a35bfa5c55e54d56abdb019daa24f3ba
Source dataset: uspto-grants-1994_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05290785

Reaction notes

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