5-Chloro-1-methylisatin

General procedure: A mixture of N-methyl-2-oxo-N-phenylacetamide 1a (0.4 mmol) and FeClGeneral procedure: A mixture of N-methyl-2-oxo-N-phenylacetamide (1a, 0.5 mmol) and PCC (0.5 mmol) were added in DMSO (2 mL) with a condenser and then heating for 3 h under air at 100 °C. After the completion of the reaction (monitored by TLC), the reaction mixture was cooled to r.t., diluted with H2O and extracted with EtOAc. The organic layer was washed with sat. brine, dried over anhydrous Na2SO4 and the solvent was evaporated to dryness. The crude residue was purified by flash chromatography on silica (PE–EtOAc, 10:1) to afford pure 1-methylindoline-2, 3-dione (2a) as a red solid (66 mg, 82percent yield). 1-Methylindoline-2, 3-dione (2a) Yield 82percent; red solid; mp 130–133 °C. General procedure: To a stirring solution of indolin-2, 3-dione (2.0g, 13.6 mmol, 1.0 equiv.) in anhydrous DMF, sodium hydride (60percent suspension inparaffin oil, 0.65 g, 16.32 mmol, 1.2 equiv.) was slowly added at 0 General procedure: To a Schlenk tube were added oxindole 1 (0.3 mmol), t-BuONO (0.6 mmol), andTHF (2 mL). Then the tube was stirred at 50 °C under 1 atm of O2 for the indicatedtime until complete consumption of starting material monitored by TLC analysis.After the reaction was finished, the reaction mixture was washed with brine. The aqueous phase was re-extracted with ethyl acetate. The combined organic extractswere dried over Na2SO4, removal of the solvent under vacuum afforded the crudeproduct, which was purified further by column chromatography using hexane-ethylacetate.General procedure: To a Schlenk tube were added indolin-2-one 1 (0.3 mmol), t-BuOOH (0.6 mmol), and DCE (2 mL). Then the tube was stirred at 85 oC under air for the indicated time until complete consumption of starting material monitored by TLC analysis. After the reaction was finished, the reaction mixture was washed with brine. The aqueous phase was re-extracted with ethyl acetate (3×10 mL). The combined organic extracts were dried over Na2SO4, removal of the solvent under vacuum afforded the crude product, which was purified further by column chromatography using hexane-ethyl acetate (10:1).In an open environment, lmmo 1 of compound of formula (I) and 6 ml of solvent toluene are added to the kettle at room temperature and then0.07 mmol of Cu (acac) 2 catalyst and 80 mg of a mixture of HSiEt2Me and 1-butyl-3-methylimidazolium trifluoromethanesulfonimide salt in a mass ratio of 1: 4 were added and the temperature was gradually increased to 80 ° with stirring C reaction 7h, after the reaction was cooled to room temperature, the mixture was added 9 times the solvent amount of a mixture of ether and water, wherein the mass ratio of ether and water 1: 1, the aqueous phase was extracted with ether, the organic layer was combined The mixture was dried over anhydrous magnesium sulfate, filtered, and evaporated. The residue was purified by column chromatography on silica gel to give the compound of formula (II). The yield was 98.9percent and the purity was 98.8percent (HPLC).General procedure: In a 4 mL vial, the starting indole 5 (0.27 mmol) was dissolved in a 2:1 mixture of DMSO and H2O (2.7 mL, 0.1 M). IBX-SO3K (2; 322 mg, 0.81 mmol, 3 equiv) followed by NaI (48 mg, 0.32 mmol, 1.2 equiv) were added to the reaction mixture at r.t. The mixture was then stirred for 16 h at 60 °C. Upon full conversion (as indicated by TLC, eluent: pentanes–EtOAc, 60:40), the mixture was added to H2O (30 mL) and extracted with EtOAc (3 × 10 mL). The combined organic layers were washed with brine (15 mL) and dried (Na2SO4). The solvent was re-moved under reduced pressure and the isatin product 6 was purified by column chromatography over silica gel (Table 1).General procedure: Cu(OAc)General procedure: Pd(OAc)2 (0.05 mmol), indole derivative 1 (0.5 mmol), TBHP (1 mL, 70 percent solutionin water) and CH3CN (3.0 mL) were added to a vial. The reaction mixture was stirredunder 80 °C for 1 h. After that time, the reaction mixture was quenched with saturatedNa2SO3 solution (consumption of residual TBHP) and extracted with EtOAc. Theorganic layer was separated and dried with Na2SO4. Removal of solvent followed byflash column chromatographic purification (Ethyl acetate/Petroleum ether = 5/1)afforded products.

Molecular Weight:195.60
XLogP3:1.2
Hydrogen Bond Acceptor Count:2
Exact Mass:195.0087061
Monoisotopic Mass:195.0087061
Topological Polar Surface Area:37.4
Heavy Atom Count:13
Complexity:266
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes