Potassium Carbonate → 5-(5-Phenylthiophen-2-yl)indolin-2-one

HRID 588261Notes

Reaction equation

HRID 588261 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.[C:12]1([C:18]2[S:22][C:21](B(O)O)=[CH:20][CH:19]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.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>[C:12]1([C:18]2[S:22][C:21]([C:2]3[CH:3]=[C:4]4[C:8](=[CH:9][CH:10]=3)[NH:7][C:6](=[O:11])[CH2:5]4)=[CH:20][CH:19]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 6111935-Bromo-2-oxindoleHCID 2776315(5-Phenylthiophen-2-yl)boronic acid

Product 1

HCID 904187515-(5-Phenylthiophen-2-yl)indolin-2-oneYield 29.1%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 218864351,4-Dioxane--water (1/1)Solvent

Conditions

Temperature
120 °C

Procedure

To a solution of 5-bromooxindole (100 mg, 0.572 mmol) in dioxane/H2O (3 ml/1 ml) was added Pd(PPh3)4 (55 mg, 0.047 mmol), 5-phenylthiophene-2-boronic acid (106 mg, 0.519 mmol) and potassium carbonate (196 mg, 1.42 mmol). The mixture was stirred at 120° C. for 1 hour under microwave irradiation. The residue was extracted with CHCl3, and the organic layer was washed with H2O and brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified by column chromatography (CHCl3/MeOH) to give 5-(5-phenylthiophen-2-yl)indolin-2-one (44 mg) as a pale yellow solid.

Workup

  1. extractionThe residue was extracted with CHCl3
  2. washthe organic layer was washed with H2O and brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography (CHCl3/MeOH)

Sources & evidence

ORD record
ord-7205dd245247426281bb80fafcb06709
Source dataset
uspto-grants-2016_01
Patent number
US09227962B2

Reaction notes

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