Water → 3-(4,5,2'-Trimethoxybiphenyl-2-ylmethylene)-1,3-dihydroindol-2-one

HRID 1860803

반응식

HRID 1860803 반응식
Br[C:2]1[CH:3]=[C:4]([CH:16]=[C:17]([O:21][CH3:22])[C:18]=1[O:19][CH3:20])[CH:5]=[C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[NH:8][C:7]1=[O:15].C(=O)([O-])[O-].[Na+].[Na+].[CH3:29][O:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1B(O)O.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>[CH3:22][O:21][C:17]1[C:18]([O:19][CH3:20])=[CH:2][C:3]([C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=2[O:30][CH3:29])=[C:4]([CH:5]=[C:6]2[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[NH:8][C:7]2=[O:15])[CH:16]=1

참가 물질

8

반응물 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 27339582-Methoxyphenylboronic acidHCID 545646043-(3-Bromo-4,5-dimethoxybenzylidene)-1,3-dihydroindol-2-one

생성물 1

HCID 542097573-(4,5,2'-Trimethoxybiphenyl-2-ylmethylene)-1,3-dihydroindol-2-one수율 64.5%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 702Ethanol용매HCID 1140Toluene용매

실험 절차

Tetrakis(triphenylphosphine)palladium(0) (0.02 g, 0.02 mmol) was added to a solution of 3-(3-bromo-4,5-dimethoxybenzylidene)-1,3-dihydroindol-2-one (0.20 g, 0.56 mmol) in toluene (1 ml) and ethanol (1 ml), followed by addition of 2M aqueous sodium carbonate (1.1 ml, 2.2 mmol). To this mixture was added 2-methoxyphenylboronic acid (0.09 g, 0.62 mmol), and the mixture was held at 100° C. in a sealed tube for 12 hours. The reaction mixture was added to water (50 ml) and extracted with ethyl acetate (2×100 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. Chromatography (silica, 30-40% ethyl acetate/hexanes) afforded 0.14 g (64%) of 3-(4,5,2′-trimethoxybiphenyl-2-ylmethylene)-1,3-dihydroindol-2-one as an orange solid.

후처리

  1. extractionextracted with ethyl acetate (2×100 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

출처 및 근거

ORD 기록
ord-bd2de0c8508c47a381f3b8d853db6c8e
출처 데이터셋
uspto-grants-2003_03
특허 번호
US06531502B1

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