Benzyl Bromide → HCID 23152883, compound

HRID 1012268Notes

Reaction equation

HRID 1012268 reaction equation
[CH:1]1([C:7]2[C:8]3[CH:26]=[CH:25][C:24]([C:27]([O:29][CH2:30][CH3:31])=[O:28])=[N:23][C:9]=3[N:10]3[C:16]=2[C:15]2[CH:17]=[CH:18][C:19]([OH:21])=[CH:20][C:14]=2[C:13](=[O:22])[CH2:12][CH2:11]3)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].[CH2:38](Br)[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1.C(=O)([O-])O.[Na+]>CN(C)C=O>[CH2:38]([O:21][C:19]1[CH:18]=[CH:17][C:15]2[C:16]3[N:10]([CH2:11][CH2:12][C:13](=[O:22])[C:14]=2[CH:20]=1)[C:9]1[N:23]=[C:24]([C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH:25]=[CH:26][C:8]=1[C:7]=3[CH:1]1[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1)[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1

Participants

6

Reactant 4

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 23152396HCID 23152396, compound

Product 1

HCID 23152883HCID 23152883, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of ethyl 12-cyclohexyl-3-hydroxy-6,7-dihydro-5-oxo-7a,8-diazadibenzo[a,e]azulene-9-carboxylate (50 mg, 0.12 mmol) in N,N-dimethylformamide (1 ml) were added potassium carbonate (20 mg, 0.15 mmol) and benzyl bromide (0.02 ml, 0.14 mmol), and the mixture was stirred at 80° C. for 3 hr. The reaction mixture was allowed to cool to room temperature. To the reaction mixture was added saturated aqueous sodium hydrogen carbonate solution and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. After filtration, the solvent was evaporated under reduced pressure and the obtained residue was purified by silica gel chromatography (hexane:ethyl acetate=3:1) to give ethyl 3-benzyloxy-12-cyclohexyl-6,7-dihydro-5-oxo-7a,8-diazadibenzo[a,e]azulene-9-carboxylate (50 mg, yield 82%).

Workup

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

Sources & evidence

ORD record
ord-2cfa42a2eb284f028c0adcebf36a1197
Source dataset
uspto-grants-2011_07
Patent number
US07977331B1

Reaction notes

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