Water → methyl 13-cyclohexyl-6,7-dihydro-5H-pyrrolo[2',1':3,4][1,4]diazepino[1,2-a]indole-10-carboxylate

HRID 1012261Notes

Reaction equation

HRID 1012261 reaction equation
Cl[CH2:2][CH2:3][CH2:4][N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([C:14]([O:16][CH3:17])=O)[CH:12]=2)[C:7]([CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)=[C:6]1[C:24]1[NH:25][CH:26]=[CH:27][CH:28]=1.[H-].[Na+].[OH2:31]>CN(C)C=O>[CH:18]1([C:7]2[C:8]3[CH:9]=[CH:10][C:11]([C:14]([O:16][CH3:17])=[O:31])=[CH:12][C:13]=3[N:5]3[CH2:4][CH2:3][CH2:2][N:25]4[CH:26]=[CH:27][CH:28]=[C:24]4[C:6]=23)[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1

Participants

5

Reactant 3

HCID 962WaterHCID 24758Sodium hydrideHCID 23152428HCID 23152428, compound

Product 1

HCID 23152770methyl 13-cyclohexyl-6,7-dihydro-5H-pyrrolo[2',1':3,4][1,4]diazepino[1,2-a]indole-10-carboxylateYield 77%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of methyl 1-(3-chloropropyl)-3-cyclohexyl-2-(1H-pyrrol-2-yl)-1H-indole-6-carboxylate (130 mg, 0.326 mmol) in N,N-dimethylformamide (4 ml) was added sodium hydride (17 mg, 0.424 mmol) under ice-cooling, and the mixture was stirred for 1 hr. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. After filtration, the solvent was evaporated under reduced pressure and the residue was purified by silica gel chromatography (hexane:ethyl acetate=4:1) to give methyl 13-cyclohexyl-6,7-dihydro-5H-pyrrolo[2′,1′:3,4][1,4]diazepino[1,2-a]indole-10-carboxylate (91 mg, yield 77%).

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed successively with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationAfter filtration
  6. customthe solvent was evaporated under reduced pressure
  7. customthe residue was purified by silica gel chromatography (hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-c95bb01e44b24ea19a2ff5bf81d71ad8
Source dataset
uspto-grants-2011_07
Patent number
US07977331B1

Reaction notes

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