Water → 3-(3'-Ethoxy-6-methoxybiphenyl-3-ylmethylene)-1,3-dihydroindol-2-one

HRID 24403ノート

反応式

HRID 24403 の反応式
Br[C:2](=[C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[NH:13][C:12]1=[O:20])[C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][CH:4]=1.C(=O)([O-])[O-].[Na+].[Na+].[CH2:27]([O:29][C:30]1[CH:31]=[C:32](B(O)O)[CH:33]=[CH:34][CH:35]=1)[CH3:28].O>C1(C)C=CC=CC=1.C(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>[CH2:27]([O:29][C:30]1[CH:35]=[C:34]([C:5]2[C:6]([O:9][CH3:10])=[CH:7][CH:8]=[C:3]([CH:2]=[C:11]3[C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[NH:13][C:12]3=[O:20])[CH:4]=2)[CH:33]=[CH:32][CH:31]=1)[CH3:28]

参加物

8

反応物 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 27739203-Ethoxybenzeneboronic acidHCID 542354863-(Bromo-4-methoxybenzylidene)-1,3-dihydroindol-2-one

生成物 1

HCID 539951903-(3'-Ethoxy-6-methoxybiphenyl-3-ylmethylene)-1,3-dihydroindol-2-one収率 397.2%

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 702Ethanol溶媒HCID 1140Toluene溶媒

実験手順

Tetrakis(triphenylphosphine)palladium(0) (0.02 g, 0.02 mmol) was added to a solution of 3-(bromo-4-methoxy-benzylidene)-1,3-dihydroindol-2-one (0.2 g, 0.61 mmol) in toluene (1 ml) and ethanol (1 ml), followed by addition of 2M aqueous sodium carbonate (1.2 ml, 2.4 mmol). To this mixture was added 3-ethoxyphenylboronic acid (0.11 g, 0.67 mmol), and the mixture was held at 100° C. in a sealed tube for 12 hours. The reaction mixture was added to water (40 ml) and extracted with ethyl acetate (75 ml). The combined organic layers were washed with saturated aqueous sodium bicarbonate (50 ml) and brine (50 ml). The organic layer was dried over magnesium sulfate and concentrated. The resulting solid was triturated with dichloromethane/hexanes to afford 0.9 g (39%) of 3-(3′-ethoxy-6-methoxy-biphenyl-3-ylmethylene)-1,3-dihydroindol-2-one as a yellow solid.

後処理

  1. extractionextracted with ethyl acetate (75 ml)
  2. washThe combined organic layers were washed with saturated aqueous sodium bicarbonate (50 ml) and brine (50 ml)
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe resulting solid was triturated with dichloromethane/hexanes

出典と根拠

ORDレコード
ord-e32d1bceb1224598860b29e5d8e958ee
出典データセット
uspto-grants-2005_02
特許番号
US06855730B2

反応ノート

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