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Potassium Carbonate → methyl 1-(3-methoxypropyl)-7-[4-(2-propoxyethoxy)phenyl]-2,3-dihydro-1H-1-benzazepine-4-carboxylate

HRID 587083
ノート
印刷プレビュー

反応式

HRID 587083 の反応式
Br[C:2]1[CH:3]=[CH:4][C:5]2[N:11]([CH2:12][CH2:13][CH2:14][O:15][CH3:16])[CH2:10][CH2:9][C:8]([C:17]([O:19][CH3:20])=[O:18])=[CH:7][C:6]=2[CH:21]=1.B([O-])([O-])O[C:24]1[CH:29]=[CH:28][C:27]([O:30][CH2:31][CH2:32][O:33][CH2:34][CH2:35][CH3:36])=[CH:26][CH:25]=1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C(CCO)=CC=CC=1.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>[CH3:16][O:15][CH2:14][CH2:13][CH2:12][N:11]1[C:5]2[CH:4]=[CH:3][C:2]([C:24]3[CH:29]=[CH:28][C:27]([O:30][CH2:31][CH2:32][O:33][CH2:34][CH2:35][CH3:36])=[CH:26][CH:25]=3)=[CH:21][C:6]=2[CH:7]=[C:8]([C:17]([O:19][CH3:20])=[O:18])[CH2:9][CH2:10]1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 22328931methyl 7-bromo-1-(3-methoxypropyl)-2,3-dihydro-1H-1-benzazepine-4-carboxylateHCID 867568144-(2-Propoxyethoxy)phenyl borate

生成物 1

HCID 22329044methyl 1-(3-methoxypropyl)-7-[4-(2-propoxyethoxy)phenyl]-2,3-dihydro-1H-1-benzazepine-4-carboxylate収率 65.3%

試薬・触媒・溶媒 2

HCID 178418397
HCID 178418397、化合物
触媒
HCID 66602552Toluene-ethanol water溶媒

実験手順

A mixture of methyl 7-bromo-1-(3-methoxypropyl)-2,3-dihydro-1H-1-benzazepine-4-carboxylate (450 mg), 4-(2-propoxyethoxy)phenyl borate (313 mg) and potassium carbonate (351 mg) in toluene-ethanol-water (15-1.5-1.5 ml) was stirred at room temperature for 1 hour under argon atmosphere. To the reaction system was added tetrakistriphenylphosphinepalladium (73 mg), and the mixture was heated to reflux for 20 hours. After cooled to room temperature, the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine and dried with magnesium sulfate. After concentration under reduced pressure, the residue was separated and purified with column chromatography (ethyl acetate:hexane=1:4→1:2) to give methyl 1-(3-methoxypropyl)-7-[4-(2-propoxyethoxy)phenyl]-2,3-dihydro-1H-1-benzazepine-4-carboxylate (376 mg) as yellow oil.

後処理

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 20 hours
  3. temperatureAfter cooled to room temperature
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with water and saturated brine
  6. dry with materialdried with magnesium sulfate
  7. concentrationAfter concentration under reduced pressure
  8. customthe residue was separated
  9. custompurified with column chromatography (ethyl acetate:hexane=1:4→1:2)

出典と根拠

ORDレコード
ord-19f56272443e46d9a9a5fb9640df42dc
出典データセット
uspto-grants-2005_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06936602B1

反応ノート

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