Potassium Carbonate → 5-(Oxazol-5-yl)-1,3-dihydroindol-2-one

HRID 748528Notes

Reaction equation

HRID 748528 reaction equation
[O:1]=[C:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH:11]=[O:12])[CH:8]=2)[NH:3]1.S([CH2:23][N+:24]#[C-:25])(C1C=CC(C)=CC=1)(=O)=O.C(=O)([O-])[O-].[K+].[K+]>CO>[O:12]1[C:11]([C:7]2[CH:8]=[C:9]3[C:4](=[CH:5][CH:6]=2)[NH:3][C:2](=[O:1])[CH2:10]3)=[CH:25][N:24]=[CH:23]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 161915Tosylmethyl isocyanideHCID 597510372,3-Dihydro-2-oxo-1H-indole-5-carboxaldehyde

Product 1

HCID 110089415-(Oxazol-5-yl)-1,3-dihydroindol-2-oneYield 53%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 2-oxoindoline-5-carbaldehyde (60 mg, 0.38 mmol), tosylmethyl isocyanide (145 mg, 0.75 mmol) and potassium carbonate (103 mg, 0.75 mmol) in methanol (20 mL) was heated at reflux for 2 h. The mixture was concentrated in vacuo and diluted with an aqueous saturated solution of sodium hydrogencarbonate and extracted with methylene chloride. The combined organic layers were dried (Na2SO4) and evaporated in vacuo. The crude product was purified on a silica gel column using heptane/ethyl acetate, (1:4), as the eluent to give 40 mg (53% yield) of the title compound: 1H NMR (DMSO-d6, 300 M ) δ 10.54 (br s, 1 H), 8.36 (br s, 1 H), 7.64-7.44 (m, 3 H), 6.89 (d, J=8 Hz, 1 H), 3.54 (br s, 2 H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 h
  3. concentrationThe mixture was concentrated in vacuo
  4. additiondiluted with an aqueous saturated solution of sodium hydrogencarbonate
  5. extractionextracted with methylene chloride
  6. dry with materialThe combined organic layers were dried (Na2SO4)
  7. customevaporated in vacuo
  8. customThe crude product was purified on a silica gel column

Sources & evidence

ORD record
ord-7144f2355180448d8e34ded729e0840b
Source dataset
uspto-grants-2008_07
Patent number
US07399780B2

Reaction notes

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