Potassium Carbonate → 1-formyl-7-(4-methylphenyl)-N-[4-[[N-methyl-N-(tetrahydro-2H-pyran-4-yl)amino]methyl]phenyl]-2,3-dihydro-1-benzazepine-4-carboxamide

HRID 1277302노트

반응식

HRID 1277302 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]([CH:23]=[O:24])[CH2:21][CH2:20][C:19]([C:25]([NH:27][C:28]3[CH:33]=[CH:32][C:31]([CH2:34][N:35]([CH3:42])[CH:36]4[CH2:41][CH2:40][O:39][CH2:38][CH2:37]4)=[CH:30][CH:29]=3)=[O:26])=[CH:18][C:17]=2[CH:43]=1.C(=O)([O-])[O-].[K+].[K+]>O.C(O)C.C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH: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:43][C:17]=2[CH:18]=[C:19]([C:25]([NH:27][C:28]2[CH:33]=[CH:32][C:31]([CH2:34][N:35]([CH3:42])[CH:36]3[CH2:37][CH2:38][O:39][CH2:40][CH2:41]3)=[CH:30][CH:29]=2)=[O:26])[CH2:20][CH2:21]1)=[O:24]

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 22329057HCID 22329057, 화합물HCID 866453334-Methylphenyl borate

생성물 1

HCID 184726701-formyl-7-(4-methylphenyl)-N-[4-[[N-methyl-N-(tetrahydro-2H-pyran-4-yl)amino]methyl]phenyl]-2,3-dihydro-1-benzazepine-4-carboxamide수율 33%

시약·촉매·용매 2

HCID 8857Ethyl Acetate용매HCID 86587398Ethanol toluene water용매

실험 절차

In water/ethanol/toluene (1:1:10, 60.0 ml) were dissolved 4-methylphenyl borate (658 mg) and 7-bromo-1-formyl-N-[4-[[N-methyl-N-(tetrahydro-2H-pyran-4-yl)amino]methyl]phenyl]-2,3-dihydro-1-benzazepine-4-carboxamide (20 g), and to the mixture was added potassium carbonate (1.34 g). Under argon atmosphere, the mixture was stirred for 30 minutes, and to the mixture was added tetrakistriphenylphosphine palladium (186 mg). Under argon atmosphere, the mixture was ref luxed for 17 hours, and the mixture was dilute with ethyl acetate (750 ml). The mixture was washed with water (200 ml) and saturated brine (100 ml), and 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 (150 g, ethyl acetate ethyl acetate/ethanol=20:1) and recrystallized from ethanol to give 1-formyl-7-(4-methylphenyl)-N-[4-[[N-methyl-N-(tetrahydro-2H-pyran-4-yl)amino]methyl]phenyl]-2,3-dihydro-1-benzazepine-4-carboxamide (Compound 317) (669 mg, 33%).

후처리

  1. waitUnder argon atmosphere, the mixture was ref luxed for 17 hours
  2. washThe mixture was washed with water (200 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 (150 g, ethyl acetate ethyl acetate/ethanol=20:1)
  6. customrecrystallized from ethanol

출처 및 근거

ORD 기록
ord-076c575152e14c399d35b3478aebccd4
출처 데이터셋
uspto-grants-2000_12
특허 번호
US06166006

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