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

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[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

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실험 절차

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).