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Oxalic Acid → 8,9-dihydro-7-[(hydroxy)(1-trityl-1H-imidazol-2-yl)methyl]-10-methylpyrido[1,2-a]indol-6(7H)-one

HRID 1681718
Notes
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Reaction equation

HRID 1681718 reaction equation
C(NC(C)C)(C)C.C([Li])CCC.[CH3:13][C:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:16]2[C:23](=[O:27])[CH2:24][CH2:25][CH2:26][C:15]=12.[C:28]([N:47]1[CH:51]=[CH:50][N:49]=[C:48]1[CH:52]=[O:53])([C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.C(O)(=O)C(O)=O>O1CCCC1.CCCCCC.O>[OH:53][CH:52]([C:48]1[N:47]([C:28]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)([C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)[C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[CH:51]=[CH:50][N:49]=1)[CH:24]1[C:23](=[O:27])[N:16]2[C:17]3[C:22]([C:14]([CH3:13])=[C:15]2[CH2:26][CH2:25]1)=[CH:21][CH:20]=[CH:19][CH:18]=3
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 5

HCID 971Oxalic AcidHCID 7912DiisopropylamineHCID 6182531-(triphenylmethyl)-1H-imidazole-2-carbaldehydeHCID 1107438710-methyl-8,9-dihydropyrido[1,2-a]indol-6(7H)-oneHCID 178418339Butyllithium

Product 1

HCID 15051930
8,9-dihydro-7-[(hydroxy)(1-trityl-1H-imidazol-2-yl)methyl]-10-methylpyrido[1,2-a]indol-6(7H)-one
Yield 68.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent3×HCID 8058HexaneSolvent

Procedure

To a solution of diisopropylamine (557 mg) in tetrahydrofuran (15 ml) at -70° C. under a nitrogen atmosphere was added 1.64M butyllithium in hexane (3.35 ml). After being stirred at the same temperature for 20 minutes, the mixture was treated with a solution of 8,9-dihydro-10-methylpyrido[1,2-a]indol-6(7H)-one (995 mg) in tetrahydrofuran (10 ml) over 15 minutes. The mixture was stirred at -70° C. for 30 minutes, and a solution of 1-trityl-1H-imidazole-2-carbaldehyde (1.69 g) in tetrahydrofuran (20 ml) was added dropwise over 10 minutes. After the mixture was stirred at -70° C. for further 70 minutes, it was diluted with chilled water, neutralized with an aqueous solution of oxalic acid, and extracted with chloroform. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, and evaporated in vacuo. Purification of the residue with silica gel column chromatography (20% ethyl acetate-chloroform) gave 8,9-dihydro-7-[(hydroxy)-(1-trityl-1H-imidazol-2-yl)methyl]-10-methylpyrido[1,2-a]indol-6(7H)-one (1.85 g)

Workup

  1. stirringThe mixture was stirred at -70° C. for 30 minutes
  2. stirringAfter the mixture was stirred at -70° C. for further 70 minutes
  3. extractionextracted with chloroform
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated in vacuo
  7. customPurification of the residue with silica gel column chromatography (20% ethyl acetate-chloroform)

Sources & evidence

ORD record
ord-b06b5f6eee0240e783af5ac20bdadcf4
Source dataset
uspto-grants-1992_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05173493

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes