Ethanol → Methyl 1-benzazepine-4-carboxylate

HRID 586850노트

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HRID 586850 반응식
Br[C:2]1[CH:3]=[CH:4][C:5]2[N:11](C(OC(C)(C)C)=O)[CH2:10][CH2:9][C:8]([C:19]([O:21][CH3:22])=[O:20])=[CH:7][C:6]=2[CH:23]=1.B([O-])([O-])OC1C=CC(OCC)=C(OCC)C=1.C(=O)([O-])[O-].[K+].[K+].C(O)C>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1(C)C=CC=CC=1>[N:11]1[C:5]2[CH:4]=[CH:3][CH:2]=[CH:23][C:6]=2[CH2:7][C:8]([C:19]([O:21][CH3:22])=[O:20])=[CH:9][CH:10]=1

참가 물질

7

반응물 4

HCID 702EthanolHCID 11430Potassium CarbonateHCID 22329270HCID 22329270, 화합물HCID 867567843,4-Diethoxyphenyl borate

생성물 1

HCID 69369751Methyl 1-benzazepine-4-carboxylate수율 247%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 1140Toluene용매

실험 절차

A mixture of methyl 7-bromo-1-(t-butoxycarbonyl)-2,3-dihydro-1H-1-benzazepine-4-carboxylate (1.0 g), 3,4-diethoxyphenyl borate (0.63 g), 1M potassium carbonate solution (8 ml), ethanol (8 ml) and toluene (50 ml) was stirred under argon atmosphere at room temperature for 30 minutes. To the mixture was added tetrakis(triphenylphosphine)palladium (0.12 g), and the mixture was refluxed overnight under argon atmosphere and extracted with ethyl acetate. The organic layer was washed with water and saturated brine and dried with anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified with silica gel column chromatography (ethyl acetate/hexane) to give methyl 1-benzazepine-4-carboxylate (1.3 g) as colorless crystals.

후처리

  1. temperaturethe mixture was refluxed overnight under argon atmosphere
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water and saturated brine
  4. dry with materialdried with anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified with silica gel column chromatography (ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-af3856b95d894b0a8f6cddba41217740
출처 데이터셋
uspto-grants-2005_08
특허 번호
US06936602B1

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