3-Nitrophenylboronic Acid → 5-(3-nitrophenyl)-1,3-dihydro-2H-indol-2-one

HRID 1264486Notes

Reaction equation

HRID 1264486 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[CH2:5]2.[N+:12]([C:15]1[CH:16]=[C:17](B(O)O)[CH:18]=[CH:19][CH:20]=1)([O-:14])=[O:13].C(=O)([O-])[O-].[K+].[K+]>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>[N+:12]([C:15]1[CH:20]=[C:19]([C:2]2[CH:3]=[C:4]3[C:8](=[CH:9][CH:10]=2)[NH:7][C:6](=[O:11])[CH2:5]3)[CH:18]=[CH:17][CH:16]=1)([O-:14])=[O:13]

Participants

7

Reactant 3

HCID 16773-Nitrophenylboronic AcidHCID 11430Potassium CarbonateHCID 6111935-Bromo-2-oxindole

Product 1

HCID 102206615-(3-nitrophenyl)-1,3-dihydro-2H-indol-2-oneYield 65%

Reagents, catalysts & solvents 3

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

Procedure

5-bromo-2-indolinone (1.08 g, 5.09 mmol) and tetrakistriphenyl phosphine Pd (0) (0.273 g) were stirred under an atmosphere of nitrogen in ethylene glycol dimethyl ether (35 mL). After 15 minutes, 3-nitrophenyl boronic acid (1.70 g, 10.2 mmol) was added, followed by potassium carbonate (4.24 g, 30.7 mmol) in water (15 mL). The reaction was heated to reflux overnight, cooled to room temperature and then filtered. Saturated ammonium chloride was added. The water layer was extracted with ethyl acetate (3×20 mL). The combined organic layer was dried MgSO4, filtered, and solvent removed in vacuo. Product purified by flash silica gel chromatography; eluted: 3:2 hexane; ethyl acetate, to give 5-(3-Nitro-phenyl)-1,3-dihydro-indol-2-one (0.084 g, 65%), Mp=269° C.; 1H NMR (DMSO-d6) δ 10.5 (s, 1H), 8.38-8.36 (m, 1H) 8.17-8.14 (m, 1H), 8.10-8.07 (m, 1H), 7.75-7.60 (m, 3H), 6.95 (d, 1H, J=8.1 Hz), 3.57 (s, 2H); IR (KBr) 3420, 3190, 1700 cm−1; MS (EI) m/z 253 (M−H)−; CHN calculated for C14H10N2O: C, 66.14; H. 3.96; N, 11.02; Found: C, 64.59; H, 4.16; N, 9.43.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux overnight
  3. filtrationfiltered
  4. additionSaturated ammonium chloride was added
  5. extractionThe water layer was extracted with ethyl acetate (3×20 mL)
  6. filtrationfiltered
  7. customsolvent removed in vacuo
  8. customProduct purified by flash silica gel chromatography
  9. washeluted

Sources & evidence

ORD record
ord-77a7e3a28d17402bbc09a70575d8e84c
Source dataset
uspto-grants-2003_04
Patent number
US06544970B2

Reaction notes

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