Potassium Carbonate → Methyl 7-(4-morpholinophenyl)-2,3-dihydro-1-benzothiepine-4-carboxylate

HRID 566079ノート

反応式

HRID 566079 の反応式
Br[C:2]1[CH:3]=[CH:4][C:5]2[S:11][CH2:10][CH2:9][C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:7][C:6]=2[CH:16]=1.B([O-])([O-])O[C:19]1[CH:24]=[CH:23][C:22]([N:25]2[CH2:30][CH2:29][O:28][CH2:27][CH2:26]2)=[CH:21][CH:20]=1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.C(O)C.O>[O:28]1[CH2:29][CH2:30][N:25]([C:22]2[CH:23]=[CH:24][C:19]([C:2]3[CH:3]=[CH:4][C:5]4[S:11][CH2:10][CH2:9][C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:7][C:6]=4[CH:16]=3)=[CH:20][CH:21]=2)[CH2:26][CH2:27]1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 18472606HCID 18472606、化合物HCID 867561794-Morpholinophenyl borate

生成物 1

HCID 18472523Methyl 7-(4-morpholinophenyl)-2,3-dihydro-1-benzothiepine-4-carboxylate収率 74.4%

試薬・触媒・溶媒 1

HCID 86587398Ethanol toluene water溶媒

実験手順

Under argon atmosphere, a mixture of methyl 7-bromo-2,3-dihydro-1-benzothiepine-4-carboxylate (0.70 g), 4-morpholinophenyl borate (581.3 mg) and potassium carbonate (0.65 g) in toluene/ethanol/water (20/2/2 ml) was stirred at room temperature for 1 hour. To the mixture was added tetrakistriphenylphosphine palladium (0.14 g), and the mixture was refluxed for 20 hours and then cooled. The mixture was extracted with ethyl acetate, washed with saturated brine and dried with magnesium sulfate. Under reduced pressure, the mixture was concentrated, and the residue was purified with column chromatography (ethyl acetate/dichloromethane=1:4) to give yellow crystals of methyl 7-(4-morpholinophenyl)-2,3-dihydro-1-benzothiepine-4-carboxylate (664.4 mg).

後処理

  1. temperaturethe mixture was refluxed for 20 hours
  2. temperaturecooled
  3. extractionThe mixture was extracted with ethyl acetate
  4. washwashed with saturated brine
  5. dry with materialdried with magnesium sulfate
  6. concentrationUnder reduced pressure, the mixture was concentrated
  7. customthe residue was purified with column chromatography (ethyl acetate/dichloromethane=1:4)

出典と根拠

ORDレコード
ord-e2bf77c8705746a4b32ade1db58dd99c
出典データセット
uspto-grants-2001_01
特許番号
US06172061B2

反応ノート

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