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

HRID 586827ノート

反応式

HRID 586827 の反応式
B([O-])([O-])O[C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH3:10])=[C:5]([CH2:11][CH3:12])[CH:4]=1.Br[C:16]1[CH:17]=[CH:18][C:19]2[N:25]([CH3:26])[CH2:24][CH2:23][C:22]([C:27]([NH:29][C:30]3[CH:35]=[CH:34][C:33]([CH2:36][N:37]([CH3:44])[CH:38]4[CH2:43][CH2:42][O:41][CH2:40][CH2:39]4)=[CH:32][CH:31]=3)=[O:28])=[CH:21][C:20]=2[CH:45]=1.C(=O)([O-])[O-].[K+].[K+]>O.C(O)C.C1(C)C=CC=CC=1.C(OCC)(=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>[CH2:11]([C:5]1[CH:4]=[C:3]([C:16]2[CH:17]=[CH:18][C:19]3[N:25]([CH3:26])[CH2:24][CH2:23][C:22]([C:27]([NH:29][C:30]4[CH:31]=[CH:32][C:33]([CH2:36][N:37]([CH3:44])[CH:38]5[CH2:43][CH2:42][O:41][CH2:40][CH2:39]5)=[CH:34][CH:35]=4)=[O:28])=[CH:21][C:20]=3[CH:45]=2)[CH:8]=[CH:7][C:6]=1[CH2:9][CH3:10])[CH3:12]

参加物

7

反応物 3

HCID 11430Potassium CarbonateHCID 223290367-bromo-1-methyl-N-[4-[[N-methyl-N-(tetrahydropyran-4-yl)amino]methyl]phenyl]-2,3-dihydro-1-benzoazepine-4-carboxamideHCID 867598303,4-Diethylphenyl borate

生成物 1

HCID 223289737-(3,4-diethylphenyl)-1-methyl-N-[4-[[N-methyl-N-(tetrahydro-2H-pyran-4-yl)amino]methyl]phenyl]-2,3-dihydro-1H-1-benzazepine-4-carboxamide収率 58.4%

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 8857Ethyl Acetate溶媒HCID 86587398Ethanol toluene water溶媒

実験手順

In a mixture of water:ethanol:toluene (1:1:10, v/v, 18.0 ml) were dissolved 3,4-diethylphenyl borate (264 mg) and 7-bromo-1-methyl-N-[4-[[N-methyl-N-(tetrahydro-2H-pyran-4-yl)amino]methyl]phenyl]-2,3-dihydro-1H-1-benzazepine-4-carboxamide (406 mg), and to the solution was added potassium carbonate (162 mg). The mixture was stirred under argon atmosphere at room temperature for 30 minutes, and to the mixture was added tetrakistriphenylphosphinepalladium (39 mg). The mixture was refluxed under argon atmosphere for 13 hours, diluted with ethyl acetate and washed with water and saturated brine, 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 (45 g, ethyl acetate:ethanol=20:1) and recrystallized from ethanol to give 7-(3,4-diethylphenyl)-1-methyl-N-[4-[[N-methyl-N-(tetrahydro-2H-pyran-4-yl)amino]methyl]phenyl]-2,3-dihydro-1H-1-benzazepine-4-carboxamide (263 mg, 55%) as yellow crystals.

後処理

  1. temperatureThe mixture was refluxed under argon atmosphere for 13 hours
  2. washwashed with water and saturated brine
  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 (45 g, ethyl acetate:ethanol=20:1)
  6. customrecrystallized from ethanol

出典と根拠

ORDレコード
ord-7d9f6a93d26f4a6fbb5c93545193147a
出典データセット
uspto-grants-2005_08
特許番号
US06936602B1

反応ノート

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