Potassium Carbonate → HCID 18472248, compound

HRID 566148Notes

Reaction equation

HRID 566148 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]([S:23]([C:26]([F:29])([F:28])[F:27])(=[O:25])=[O:24])[CH2:21][CH2:20][C:19]([C:30]([O:32][CH2:33][CH3:34])=[O:31])=[CH:18][C:17]=2[CH:35]=1.C(=O)([O-])[O-].[K+].[K+]>O.C(O)C.C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH3:9][C:6]1[CH:7]=[CH:8][C:3]([C:13]2[CH:14]=[CH:15][C:16]3[N:22]([S:23]([C:26]([F:27])([F:29])[F:28])(=[O:24])=[O:25])[CH2:21][CH2:20][C:19]([C:30]([O:32][CH2:33][CH3:34])=[O:31])=[CH:18][C:17]=3[CH:35]=2)=[CH:4][CH:5]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 18472485HCID 18472485, compoundHCID 866453334-Methylphenyl borate

Product 1

HCID 18472248HCID 18472248, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 86587398Ethanol toluene waterSolvent

Procedure

In water/ethanol/toluene (1:1:10, 36.0 ml) 4-methylphenyl borate (194 mg) and ethyl 7-bromo-1-[(trifluoromethyl)sulfonyl]-2,3-dihydro-1-benzazepine-4-carboxylate (510 mg) were dissolved, and to the mixture was added potassium carbonate (395 mg). The mixture was stirred under argon atmosphere for 30 minutes, and to the mixture was added tetrakistriphenylphosphine palladium (138 mg). Under argon atmosphere, the mixture was refluxed for 17 hours, and the mixture was diluted with ethyl acetate (150 ml) and washed with water (50 ml) and saturated brine (50 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 (50 g, hexane/ethyl acetate=9:1) to give ethyl 7-(4-methylphenyl)-1-[(trifluoromethyl)sulfonyl]-2,3-dihydro-1-benzazepine-4-carboxylate (469 mg, 90%).

Workup

  1. temperatureUnder argon atmosphere, the mixture was refluxed for 17 hours
  2. washwashed with water (50 ml) and saturated brine (50 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 (50 g, hexane/ethyl acetate=9:1)

Sources & evidence

ORD record
ord-91c4779e2eec4f189ab7d091fcb82dfc
Source dataset
uspto-grants-2001_01
Patent number
US06172061B2

Reaction notes

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