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With lithium aluminium tetrahydride In diethyl ether at 0℃; for 0.75 h; Heating / reflux
To a solution of 2.00 g (8.94 mmol) 6-chlorindole-2-carboxylic acid ethyl ester in 50 ml diethyl ether were added 0.475 g (12.5 mmol) lithium aluminum hydride at 0° C. The reaction mixture was heated at reflux for 45 min and quenched by consecutive addition of 10 ml water, 10 ml aqueous 2 M sodium hydroxide solution and 10 ml water at 0° C. The aqueous layer was extracted with tert-butyl methyl ether (3*100 ml). The combined organic layers were dried over sodium sulfate and concentrated in vacuo to give the crude title compound (1.64 g; 100percent) as a white solid. MS m/e (percent): 180 (M-H+, 100).
100%
Stage #1: With lithium aluminium tetrahydride In diethyl ether at 0℃; for 0.75 h; Heating / reflux Stage #2: With sodium hydroxide; water In diethyl ether at 0℃;
To a solution of 2.00 g (8.94 mmol) 6-chlorindole-2-carboxylic acid ethyl ester in 50 ml diethyl ether were added 0.475 g (12.5 mmol) lithium aluminum hydride at 0° C. The reaction mixture was heated at reflux for 45 min and quenched by consecutive addition of 10 ml water, 10 ml aqueous 2 M sodium hydroxide solution and 10 ml water at 0° C. The aqueous layer was extracted with tert-butyl methyl ether (3*100 ml). The combined organic layers were dried over sodium sulfate and concentrated in vacuo to give the crude title compound (1.64 g; 100percent) as a white solid. MS m/e (percent): 180 (M-H+, 100).
100%
Stage #1: With lithium aluminium tetrahydride In diethyl ether at 0℃; for 0.75 h; Heating / reflux Stage #2: With sodium hydroxide; water In diethyl ether
To a solution of 2.00 g (8.94 mmol) 6-chlorindole-2-carboxylic acid ethyl ester in 50 ml diethyl ether were added 0.475 g (12.5 mmol) lithium aluminum hydride at 0° C. The reaction mixture was heated at reflux for 45 min and quenched by consecutive addition of 10 ml water, 10 ml aqueous 2 M sodium hydroxide solution and 10 ml water at 0° C. The aqueous layer was extracted with tert-butyl methyl ether (3*100 ml). The combined organic layers were dried over sodium sulfate and concentrated in vacuo to give the crude title compound (1.64 g; 100percent) as a white solid. MS m/e (percent): 180 (M-H+, 100).
ethyl 6-chloro-3-(2-(4-fluorophenyl)acetyl)-1H-indole-2-carboxylate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
95%
With tin(IV) chloride; In nitromethane; dichloromethane; at 20℃;
General procedure: To a stirred solution of the corresponding indole derivatives (5.0 mmol) in DCM(10 mL), SnCl4 (1.0 M in DCM, 7.5 mmol) was added. The reactionmixture stirred for 30 min at rt and then, the corresponding phenyl acetylchloride (6.0 mmol) was added slowly following the addition of MeNO2(10 mL). After stirring overnight at rt, the reaction was quenched withice/water, extracted with ethyl acetate, washed by 1.0 M NaOH solution threetimes and one time by brine. The solvent was removed and the product wasgenerated and used in the next step without further purification.
Chemistry
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