3-Nitrophenylboronic Acid → 3,3-Dimethyl-5-(3-nitro-phenyl)-1,3-dihydro-indol-2-one

HRID 6984

Reaction equation

HRID 6984 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2([CH3:13])[CH3:12].[N+:14]([C:17]1[CH:18]=[C:19](B(O)O)[CH:20]=[CH:21][CH:22]=1)([O-:16])=[O:15].C(=O)([O-])[O-].[K+].[K+].[Cl-].[NH4+]>C(COC)OC.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.CCOC(C)=O>[CH3:12][C:5]1([CH3:13])[C:4]2[C:8](=[CH:9][CH:10]=[C:2]([C:21]3[CH:20]=[CH:19][CH:18]=[C:17]([N+:14]([O-:16])=[O:15])[CH:22]=3)[CH:3]=2)[NH:7][C:6]1=[O:11]

Participants

9

Reactant 4

HCID 16773-Nitrophenylboronic AcidHCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 120527965-bromo-3,3-dimethyl-2,3-dihydro-1H-indol-2-one

Product 1

HCID 99257573,3-Dimethyl-5-(3-nitro-phenyl)-1,3-dihydro-indol-2-oneYield 119%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

5-bromo-1,3-dihydro-3,3-dimethyl-2H-indol-2-one (1.02 g, 4.26 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.244 g) were stirred under an atmosphere of nitrogen in dimethoxyethane (35 cm3). After 15 minutes, 3-nitrophenylboronic acid (1.43 g, 2.56 mmol) was added, followed by potassium carbonate (3.54 g, 2.56 mmol) in water (15 cm3). The reaction was heated to reflux for 2 hours and then stirred at room temperature overnight. Saturated ammonium chloride and EtOAc were added and the mixture was filtered. The aqueous layer was extracted with ethyl acetate (×2), and then the combined organic layers were dried (Na2SO4), filtered, and evaporated. The residue was purified by column chromatography (SiO2, EtOAc: hexane, gradient elution) to afford the title compound (0.86 g, 67%) mp 234–235° C.; 1H NMR (DMSO-d6) δ 3.33 (s, 6H), 6.98 (d, 1H, J=8.06 Hz), 7.61 (dd, 1H, J=1.85, 8.03 Hz), 7.73 (t, 1H, J=7.98 Hz), 7.81 (d, 1H, J=1.63 Hz), 8.11–8.18 (m, 2H), 8.42–8.43 (m, 1H), 10.5 (s, 1H); MS (EI) m/z 281; Anal. Calc. for C16H14N2O3.0.2H2O: C, 67.51; H, 4.92; N, 9.37; Found: C, 67.48; H, 5.17; N, 9.48.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 2 hours
  3. filtrationthe mixture was filtered
  4. extractionThe aqueous layer was extracted with ethyl acetate (×2)
  5. dry with materialthe combined organic layers were dried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by column chromatography (SiO2, EtOAc: hexane, gradient elution)

Sources & evidence

ORD record
ord-31d1fe9f37be4dd1a460278d3b248409
Source dataset
uspto-grants-2006_08
Patent number
US07084168B2

Linked notes

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