Ethanol → methyl 7-[4-(2-butoxyethoxy)phenyl]-1-(N,N-dimethyl-4-sulfamoylphenyl)-2,3-dihydro-1H-1-benzazepine-4-carboxylate

HRID 586948노트

반응식

HRID 586948 반응식
Br[C:2]1[CH:3]=[CH:4][C:5]2[N:11]([C:12]3[CH:17]=[CH:16][C:15]([S:18](=[O:23])(=[O:22])[N:19]([CH3:21])[CH3:20])=[CH:14][CH:13]=3)[CH2:10][CH2:9][C:8]([C:24]([O:26][CH3:27])=[O:25])=[CH:7][C:6]=2[CH:28]=1.B([O-])([O-])O[C:31]1[CH:36]=[CH:35][C:34]([O:37][CH2:38][CH2:39][O:40][CH2:41][CH2:42][CH2:43][CH3:44])=[CH:33][CH:32]=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>[CH2:41]([O:40][CH2:39][CH2:38][O:37][C:34]1[CH:33]=[CH:32][C:31]([C:2]2[CH:3]=[CH:4][C:5]3[N:11]([C:12]4[CH:13]=[CH:14][C:15]([S:18](=[O:23])(=[O:22])[N:19]([CH3:20])[CH3:21])=[CH:16][CH:17]=4)[CH2:10][CH2:9][C:8]([C:24]([O:26][CH3:27])=[O:25])=[CH:7][C:6]=3[CH:28]=2)=[CH:36][CH:35]=1)[CH2:42][CH2:43][CH3:44]

참가 물질

7

반응물 4

HCID 702EthanolHCID 11430Potassium CarbonateHCID 22328934methyl 7-bromo-1-(N,N-dimethyl-4-sulfamoylphenyl)-2,3-dihydro-1H-1-benzazepine-4-carboxylateHCID 867568154-Butoxyethoxyphenyl borate

생성물 1

HCID 22328993methyl 7-[4-(2-butoxyethoxy)phenyl]-1-(N,N-dimethyl-4-sulfamoylphenyl)-2,3-dihydro-1H-1-benzazepine-4-carboxylate수율 80.4%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 1140Toluene용매

실험 절차

A mixture of methyl 7-bromo-1-(N,N-dimethyl-4-sulfamoylphenyl)-2,3-dihydro-1H-1-benzazepine-4-carboxylate (0.35 g), 4-(2-butoxyethoxy)phenyl borate (0.19 g), 1M potassium carbonate solution (2 ml), ethanol (2 ml) and toluene (50 ml) was stirred under argon atmosphere at room temperature for 30 minutes. To the mixture was added tetrakis(triphenylphosphine)palladium (0.04 g), and the mixture was refluxed under argon atmosphere for 6 hours and extracted with ethyl acetate. The organic layer was washed with water and saturated brine and dried with anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified with silica gel column chromatography (ethyl acetate/hexane) to give methyl 7-[4-(2-butoxyethoxy)phenyl]-1-(N,N-dimethyl-4-sulfamoylphenyl)-2,3-dihydro-1H-1-benzazepine-4-carboxylate (0.35 g) as colorless crystals.

후처리

  1. temperaturethe mixture was refluxed under argon atmosphere for 6 hours
  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-ae80f33a069e4261bafceab0d7c16472
출처 데이터셋
uspto-grants-2005_08
특허 번호
US06936602B1

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