1-(5-CHLORO-1H-INDOL-3-YL)ETHANONE

General procedure: A 10 mL glass vessel suited for the monomode microwave oven was charged with 1 mmol substrate, 1 mmol acid anhydride, 0.01 mmol metal triflate, and 1 mmol ionic liquid. Next, the vessel was sealedwith a Teflon cap and irradiated in a monomode microwave oven at many different reaction conditions(temperature and time) to find the optimal condition. Upon completion, the vessel was cooled down toroom temperature and the mixture was extracted with Et2O (5 × 10 mL). The ether layer was decantedand washed with water (2 × 10 mL), saturated aqueous NaHCO3 (2 × 20 mL), and brine (2 × 10 mL).The organic layer was dried over MgSO4, filtered, and the solvent was removed by a rotary evaporator.The isolated yield was determined after purification by flash chromatography (silica gel, n-hexane/ethylacetate, gradient 10:0 to 8:2).A mixture of compound 5a (9.1 g, 0.06 mol), glacial acetic acid (9.1 mL) and acetic anhydride (91 mL) was heated to reflux for 20 h. Upon cooling to room temperature, the solid was collected by filtration and purified by silica gel column chromatography. 6a was obtained as a white solid (5.2 g, 45percent). m.p. 246-247 °C. ESI-MS m/z: 194.1 (Cl = 35), 196.0 (Cl = 37) [M + H]

Molecular Weight:193.63
XLogP3:2.7
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:1
Exact Mass:193.0294416
Monoisotopic Mass:193.0294416
Topological Polar Surface Area:32.9
Heavy Atom Count:13
Complexity:219
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes