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 1277302ノート

反応式

HRID 1277302 の反応式
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]

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 22329057HCID 22329057、化合物HCID 866453334-Methylphenyl borate

生成物 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-carboxamide収率 33%

試薬・触媒・溶媒 2

HCID 8857Ethyl Acetate溶媒HCID 86587398Ethanol toluene water溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-076c575152e14c399d35b3478aebccd4
出典データセット
uspto-grants-2000_12
特許番号
US06166006

反応ノート

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