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

HRID 566123노트

반응식

HRID 566123 반응식
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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 8857Ethyl Acetate용매HCID 86587398Ethanol toluene water용매

실험 절차

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 tert-butyl 1-methyl-7-(4-methylphenyl)-2,3-dihydro-1-benzoazepine-4-carboxylate (422 mg, 72%).

후처리

  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)

출처 및 근거

ORD 기록
ord-5d2a8db685864f9782e45ea789f8e1a2
출처 데이터셋
uspto-grants-2001_01
특허 번호
US06172061B2

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