* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
To a stirred solution of tert-butyl 4-oxopiperidine-l-carboxylate (35.6 g, 178.89 mmol) in chloroform (260 ml) at RT was added pyrrolidine (19 ml, 223.61 mmol) dropwise over 1 h. The reaction mixture was stirred for a further Ih at RT then prop-2-ynamide (16 g, 223.61 mmol) was added and the reaction mixture reluxed under Dean-Stark conditions for 16 h. The cooled reaction mixture was filtered and the filtrate triturated with toluene and re-filtered. The filtrate was evaporated at reduced pressure to give a red / brown viscous liquid that was <n="77"/>purified by FCC (SiO2, eluting with 98:2 chloroform / MeOH) to give the title compound (4.01 g, 51.8%) as a brown oil
3-(3-nitro-5-(trifluoromethyl)phenyl)propiolamide[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
480 mg
With bis-triphenylphosphine-palladium(II) chloride; copper(II) iodide; triethylamine; In N,N-dimethyl-formamide; at 120℃; for 0.5h;Microwave irradiation;
To a solution of 1-bromo-3-nitro-S-(trifluoromethyl)benzene (1.0 g, 3.70 mmol) in degassed DMF (10 mL) were added propiolamide (511 mg, 7.40 mmol), bis(triphenylphosphine)palladium(II)dichloride (129 mg, 0.18 mmol), copper(II)iodide (71mg, 0.37 mmol) and triethylamine (1.54 mL, 11.1 mmol) at RT. The resultant mixture was heated at 120 C for 30 mm in a microwave reactor. The mixture was cooled to RT and quenched with water. The product was extracted in ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue obtained was purified by silica gel column chromatography toyield 480 mg of the desired compound. ?H NMR (400 MHz, DMSO-d6) oe 7.92 (br s, 2H),8.32 (s, 1H), 8.46 (s, 1H), 8.57-8.66 (m, 1H).
Chemistry
Pharmaceutical Intermediates
Inhibitors/Agonists
Material Science
For Research Only
120K+ Compounds
Competitive Price
1-2 Day Shipping
