Water → Methyl 7-[4-(2-butoxyethoxy)phenyl]-1-isobutyl-2,3-dihydro-1-benzazepine-4-carboxylate

HRID 587039ノート

反応式

HRID 587039 の反応式
Br[C:2]1[CH:3]=[CH:4][C:5]2[N:11]([CH2:12][CH:13]([CH3:15])[CH3:14])[CH2:10][CH2:9][C:8]([C:16]([O:18][CH3:19])=[O:17])=[CH:7][C:6]=2[CH:20]=1.B([O-])([O-])O[C:23]1[CH:28]=[CH:27][C:26]([O:29][CH2:30][CH2:31][O:32][CH2:33][CH2:34][CH2:35][CH3:36])=[CH:25][CH:24]=1.C(=O)([O-])[O-].[K+].[K+].O>C1(C)C=CC=CC=1.C(O)C.O.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>[CH2:33]([O:32][CH2:31][CH2:30][O:29][C:26]1[CH:25]=[CH:24][C:23]([C:2]2[CH:3]=[CH:4][C:5]3[N:11]([CH2:12][CH:13]([CH3:15])[CH3:14])[CH2:10][CH2:9][C:8]([C:16]([O:18][CH3:19])=[O:17])=[CH:7][C:6]=3[CH:20]=2)=[CH:28][CH:27]=1)[CH2:34][CH2:35][CH3:36]

参加物

7

反応物 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 22328913Methyl 7-bromo-1-isobutyl-2,3-dihydro-1-benzazepine-4-carboxylateHCID 867568154-Butoxyethoxyphenyl borate

生成物 1

HCID 22328949Methyl 7-[4-(2-butoxyethoxy)phenyl]-1-isobutyl-2,3-dihydro-1-benzazepine-4-carboxylate収率 62.4%

試薬・触媒・溶媒 2

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

実験手順

Methyl 7-bromo-1-isobutyl-2,3-dihydro-1-benzazepine-4-carboxylate (0.90 g) was dissolved in toluene/ethanol/water (=10/1/1, 41 ml). To the solution were added 4-(2-butoxyethoxy)phenyl borate (0.76 g) and potassium carbonate (0.18 g), and the mixture was stirred under argon atmosphere for 30 minutes. To the mixture was added tetrakistriphenylphosphinepalladium (123 mg), and the mixture was heated to reflux for 14 hours. After cooled to room temperature, the reaction solution was added to water, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine and dried with magnesium sulfate. The solvent was removed under reduced pressure, and the resulting residue was purified with silica gel column chromatography (hexane/ethyl acetate=8/1) to give methyl 7-[4-(2-butoxyethoxy)phenyl]-1-isobutyl-2,3-dihydro-1-benzazepine-4-carboxylate (0.75 g).

後処理

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 14 hours
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried with magnesium sulfate
  6. customThe solvent was removed under reduced pressure
  7. customthe resulting residue was purified with silica gel column chromatography (hexane/ethyl acetate=8/1)

出典と根拠

ORDレコード
ord-2477771bbe784c2da1aecfa9e648386b
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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