Phenylboronic Acid → 7-methyl-6-phenyl-1H-indole-2,3-dione

HRID 2105112Notes

Reaction equation

HRID 2105112 reaction equation
Br[C:2]1[C:10]([CH3:11])=[C:9]2[C:5]([C:6](=[O:13])[C:7](=[O:12])[NH:8]2)=[CH:4][CH:3]=1.[C:14]1(B(O)O)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C([O-])(O)=O.[Na+]>COCCOC.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>[CH3:11][C:10]1[C:2]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:3][CH:4]=[C:5]2[C:9]=1[NH:8][C:7](=[O:12])[C:6]2=[O:13]

Participants

7

Reactant 3

HCID 66827Phenylboronic AcidHCID 516892Sodium BicarbonateHCID 112301886-Bromo-7-methyl-1H-indole-2,3-dione

Product 1

HCID 113683787-methyl-6-phenyl-1H-indole-2,3-dioneYield 55.5%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

6-Bromo-7-methyl-1H-indole-2,3-dione (100 mg, 0.38 mmol) and phenylboronic acid (53 mg, 1.1 eq) were dissolved in 10 mL DME. Pd(PPh3)4 (22 mg, 0.05 eq) were added followed by NaHCO3 (65 mg, 2.0 eq) dissolved in 10 mL water. The mixture was refluxed for 2.5 hr and the organic solvent was removed by evaporation. The mixture was extracted with ethyl acetate and the combined organic layers were dried over Na2SO4 and purified by SiO2 chromatography to give the title compound (50 mg, 51%).

Workup

  1. temperatureThe mixture was refluxed for 2.5 hr
  2. customthe organic solvent was removed by evaporation
  3. extractionThe mixture was extracted with ethyl acetate
  4. dry with materialthe combined organic layers were dried over Na2SO4
  5. custompurified by SiO2 chromatography

Sources & evidence

ORD record
ord-535c3c60a3474bf8b77cbfb99427d749
Source dataset
uspto-grants-2009_08
Patent number
US07579313B2

Reaction notes

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