Water → N-[2'-methoxy-5'-(2-oxo-1,2-dihydroindol-3-ylidenemethyl)-biphenyl-3-yl]-acetamide

HRID 24387

Reaction equation

HRID 24387 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][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+].[C:27]([NH:30][C:31]1[CH:32]=[C:33](B(O)O)[CH:34]=[CH:35][CH:36]=1)(=[O:29])[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>[CH3:20][O:19][C:18]1[CH:17]=[CH:16][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:3][C:2]=1[C:35]1[CH:34]=[CH:33][CH:32]=[C:31]([NH:30][C:27](=[O:29])[CH3:28])[CH:36]=1

Participants

8

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 157274(3-Acetamidophenyl)boronic acidHCID 28031073-(3-Bromo-4-methoxybenzylidene)-1,3-dihydroindol-2-one

Product 1

HCID 54244688N-[2'-methoxy-5'-(2-oxo-1,2-dihydroindol-3-ylidenemethyl)-biphenyl-3-yl]-acetamideYield 22%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

Tetrakis(triphenylphosphine)palladium(0) (0.02 g, 0.02 mmol) was added to a solution of 3-(3-Bromo-4-methoxy-benzylidene)-1,3-dihydroindol-2-one (0.2 g, 0.61 mmol) in toluene (1 ml) and ethanol (2 ml), followed by addition of 2M aqueous sodium carbonate (1.2 ml, 2.4 mmol). To this mixture was added 3-acetamidophenylboronic acid (0.12 g, 0.67 mmol), and the mixture was heated to 100° C. in a sealed tube and held there for 12 hours. The reaction was then poured into 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 a waxy solid that was triturated with diethyl ether/hexanes and then dried to afford 0.05 g (22%) of N-[2′-methoxy-5′-(2-oxo-1,2-dihydroindol-3-ylidenemethyl)-biphenyl-3-yl]-acetamide as a reddish orange solid.

Workup

  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
  5. customChromatography (silica, 30-40% ethyl acetate/hexanes),afforded a waxy solid that was triturated with diethyl ether/hexanes
  6. customdried

Sources & evidence

ORD record
ord-456257a834a94d91b9f4e52c9d5e7736
Source dataset
uspto-grants-2005_02
Patent number
US06855730B2

Linked notes

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