5-BROMO-1-ETHYL-1H-INDOLE

5-Bromo-3-(2, 4-dichlorobenzoyl)-1-ethyl-1H-indole [0380] 1a) 5-Bromo-1-ethyl-1H-indole [0381] In 75 mL of anhydrous dimethylformamide, place 3.06 g (76.5 mmol) of sodium hydride in 60percent suspension in mineral oil. Stir and heat the mixture to 80° C. Add progressively, using a spatula, 5.0 g (25.5 mmol) of 5-bromo-1H-indole. Continue the heating for 30 minutes (until no further hydrogen is evolved). Cool the mixture to ambient temperature and add 4 mL (51 mmol) of iodoethane. Heat the mixture again to 80° C. for 2 hours. Hydrolyse the reaction medium. Extract with dichloromethane, dry the organic phase over anhydrous sodium sulfate and evaporate. Purify the evaporation residue by chromatography on silica gel with elution by dichloromethane (Int. 49). [0382] Yield: 89percent [0383] Yellow oilGeneral procedure: To a microwave reaction tube were added indoles (2 mmol), isatins (1 mmol) and HFIP (2 mL). After sealing the tube, the mixture was heated to 75C in an oil bath and stirred for 1 h. After completion of the reaction (monitored by TLC), the reaction mixture was cooled to room temperature, and the resulting precipitate was then filtered, washed with ether, and dried to give compound 3a-3q and 4a-4j.5-bromoindole (100 mg, 0.62 mmol), DMF (4 mL), Potassium tert-butoxide (171, 1.85 mmol, 3 eq.) was added to the reaction flask in turn.After stirring at room temperature for 5 minutes, After the potassium tert-butoxide is uniformly dispersed, Slowly inject into the reaction flaskEthyl trifluoroacetate (0.29 mL, 2.47 mmol, 4 eq.).400 W microwave irradiation for 2 minutes.After cooling to room temperature, extract twice with ethyl acetate and distilled water.Wash with saturated NaCl solution, Combine the organic phase, Drying the organic phase with anhydrous magnesium sulfate, Remove magnesium sulfate by filtration, Rotate the solvent, Column chromatography purification, Light green liquidAdd 1.5 mL of DMF to a 50 mL reaction tube at room temperature, then add 1.0 mL of trifluoroacetic acid, add 0.2 mL of water and stir.Add

Molecular Weight:224.10
XLogP3:3
Rotatable Bond Count:1
Exact Mass:222.99966
Monoisotopic Mass:222.99966
Topological Polar Surface Area:4.9
Heavy Atom Count:12
Complexity:160
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes