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With 1,1'-bis-(diphenylphosphino)ferrocene; formic acid; N-ethyl-N,N-diisopropylamine; In toluene; at 150℃; for 24h;Inert atmosphere;
General procedure: The mixture of 2-nitrobenzyl alcohol 1a-f (0.5 mmol), alcohol 2a-k (0.6 mmol), HCO2H (53 muL, 1.0 mmol), DIPEA (125 muL, 0.75 mmol), and dppf (14.1 mg, 0.025 mmol) in toluene (1.0 mL) was stirred at 150C (screw-capped vial) for 1 d under argon, cooled to r.t., then water (5mL) was added. The two layers were separated, and the aqueous phase was extracted with EtOAc (3 × 10 mL). The combined organic extracts were washed by brine, dried (anhyd Na2SO4), filtered, and concentrated. The residue was purified by flash chromatography on silica gel (100-200 mesh) to afford the desired quinoline 3a-r.
With 1,4-diaza-bicyclo[2.2.2]octane; sulfur; urea; In dimethyl sulfoxide; at 140℃; for 8h;
General procedure: To a 4-mL screw-cap vial was added 2-nitrobenzyl alcohol (15.3 mg, 0.1 mmol), phenylacetic acid (34.0 mg, 0.25 mmol), base, elemental sulfur, urea, and DMSO (0.3 mL).The reaction tube was tightly capped and the resulting mixture was then stirred at a given temperature. After completion of the reaction, the mixture was cooled to room temperature and diphenyl ether (17.2 mg, 0.1 mmol) as an internal standard was added. The organic components were then extracted into ethyl acetate (3×2 mL), washed with NaHCO3 solution (10% in water, 3×1 mL), dried over anhydrous Na2SO4, filtered, and analyzed by GC with reference to diphenyl ether.
2-((5-fluoro-1H-indol-1-yl)amino)benzaldehyde[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
79%
With tetraethylammonium iodide; acetic acid; In dichloromethane; at 20℃; for 24h;UV-irradiation;
Add 0.2mmol of indoline compound V into the 10mL reaction tube,Add 0.4mmol of o-nitrobenzyl alcohol compound VI, 0.2mmol of acetic acid, 0.2mmol of tetraethylammonium iodide, 4mL of dichloromethane, and irradiate with 385-405nm ultraviolet light at room temperature.Reaction for 24h. After the reaction, it is separated by column chromatography to obtainN-(2-arylcarboxaldehyde)-1-aminoindole derivative (R1=5-fluoro, R2=hydrogen) to obtain a brown jelly with a yield of 79%.
Chemistry
Pharmaceutical Intermediates
Inhibitors/Agonists
Material Science
For Research Only
120K+ Compounds
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