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

HRID 24403Notes

Reaction equation

HRID 24403 reaction equation
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]

Participants

8

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-e32d1bceb1224598860b29e5d8e958ee
Source dataset
uspto-grants-2005_02
Patent number
US06855730B2

Reaction notes

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