Potassium Carbonate → Tert-butyl 1-methyl-7-(4-methylphenyl)-2,3-dihydro-1-benzoazepine-4-carboxylate

HRID 2228309Notes

Reaction equation

HRID 2228309 reaction equation
B([O-])([O-])O[C:3]1[CH:8]=[CH:7][C:6]([CH3:9])=[CH:5][CH:4]=1.Br[C:13]1[CH:14]=[CH:15][C:16]2[N:22]([CH3:23])[CH2:21][CH2:20][C:19]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])=[CH:18][C:17]=2[CH:31]=1.C(=O)([O-])[O-].[K+].[K+]>O.C(O)C.C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH3:23][N:22]1[C:16]2[CH:15]=[CH:14][C:13]([C:3]3[CH:8]=[CH:7][C:6]([CH3:9])=[CH:5][CH:4]=3)=[CH:31][C:17]=2[CH:18]=[C:19]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:20][CH2:21]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 18472450HCID 18472450, compoundHCID 866453334-Methylphenyl borate

Product 1

HCID 18472637Tert-butyl 1-methyl-7-(4-methylphenyl)-2,3-dihydro-1-benzoazepine-4-carboxylateYield 72%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 86587398Ethanol toluene waterSolvent

Procedure

In water:ethanol:toluene (1:1:10, 18.0 ml) were dissolved 4-methylphenyl borate (276 mg) and tert-butyl 7-bromo-1-methyl-2,3-dihydro-1-benzoazepine-4-carboxylate (571 mg), and to the mixture was added potassium carbonate (560 mg). The mixture was stirred under argon atmosphere for 30 minutes, and to the mixture was added tetrakistriphenylphosphine palladium (78 mg). Under argon atmosphere, the mixture was refluxed for 19.5 hours. The mixture was diluted with ethyl acetate (300 ml) and washed with water (100 ml) and saturated brine (100 ml). The organic layer was dried with anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified with silica gel column chromatography (120 g, hexane→hexane:ethyl acetate=10:1) to give tertbutyl 1-methyl-7-(4-methylphenyl)-2,3-dihydro-1-benzoazepine-4-carboxylate (422 mg, 72%).

Workup

  1. temperatureUnder argon atmosphere, the mixture was refluxed for 19.5 hours
  2. washwashed with water (100 ml) and saturated brine (100 ml)
  3. dry with materialThe organic layer was dried with anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified with silica gel column chromatography (120 g, hexane→hexane:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-1144c3efac41446da82adf32ccdcc476
Source dataset
uspto-grants-2002_07
Patent number
US06413947B1

Reaction notes

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