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To a solution of 790 tert-butyl N-prop-2-ynyl carbamate (5.0 g, 32 mmol) in 20 tetrahydrofuran (100mL) were added 768 4-trifluoromethylbenzoylchloride (4.3 mL, 29 mmol), 791 dichlorobis(triphenylphosphine)palladium(II) (0.25 g, 0.36 mmol) and 18 copper(I) iodide (0.25 g, 1.3 mmol) and themixture was stirred at room temperature for 5 min. 14 Triethylamine (5.5 mL, 39 mmol) was added andthe mixture was stirred for 30 min. Using a small amount of silica gel, the insoluble material was filtered off,and the filtrate was concentrated under reduced pressure. The obtained residue was dissolved in 79acetonitrile (300 mL), and 792 <strong>[538-28-3]S-benzylisothiourea hydrochloride</strong> (7.5 g, 37 mmol) and 106 potassiumcarbonate (6.0 g, 43 mmol) were added. The reaction mixture was stirred at 70° C. overnight, 12dichloromethane was added and the mixture was washed with water. The organic layer was dried oversodium sulfate, and the desiccant was filtered off. The solvent was evaporated and the obtained residue waspurified by silica gel column chromatography (hexane/ethyl acetate) to give the 793 title compound ( 4.0g , 8.4 mmol, 26percent). MS (ESI) m/z 476 (M+H)+
26%
To a solution of tert-butyl N-prop-2-ynylcarbamate (5.0 g, 32 mmol) in tetrahydrofuran (100 mL) were added 4-trifluoromethylbenzoylchloride (4.3 mL, 29 mmol), dichlorobis(triphenylphosphine)palladium(II) (0.25 g, 0.36 mmol) and copper(I) iodide (0.25 g, 1.3 mmol) and the mixture was stirred at room temperature for 5 min. Triethylamine (5.5 mL, 39 mmol) was added and the mixture was stirred for 30 min. Using a small amount of silica gel, insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. To the obtained residue was added acetonitrile (300 mL) for dissolution and <strong>[538-28-3]S-benzylisothiourea hydrochloride</strong> (7.5 g, 37 mmol) and potassium carbonate (6.0 g, 43 mmol) were added. The reaction mixture was stirred at 70°C overnight, dichloromethane was added and the mixture was washed with water. The organic layer was dried over sodium sulfate and the desiccant was filtered off. The solvent was evaporated and the obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (4.0 g, 8.4 mmol, 26percent). MS (ESI) m/z 476 (M+H)+
tert-butyl (3-(3-amino-6-chloropyridin-2-yl)prop-2-yn-1-yl)carbamate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
86%
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; copper(l) iodide; triethylamine; In tetrahydrofuran; at 70℃; for 16h;Inert atmosphere;
A mixture of <strong>[1050501-88-6]2-bromo-6-chloropyridin-3-amine</strong> (1 g, 4.82 mmol, Fluorochem), 2-bromo-6- chloropyridin-3-amine (1 g, 4.82 mmol, Alfa Aesar), copper I iodide (0.092 g, 0.482 mmol), PdCI2(dppf) (0.353 g, 0.482 mmol) and TEA (1.008 mL, 7.23 mmol) in Tetrahydrofuran (THF) (20mL) was degassed under a flow of nitrogen for 10 min. The reaction mixture was heated to 70 C for 16h. The mixture was cooled down to RT. EtOAc (20 mL) was added and the resulting mixture was filtered through Celite (2.5 g cartridge). The residual solild was washed with additional EtOAc (2 x 20 mL) The filtrate was collected and washed with saturated ammonium chloride solution (50 mL), water (50 mL), brine (50 ml.) and dried over MgS04. The volatiles were removed under reduced pressure to give a residue that was purified by column chromatography on Silica (120 g Cartridge, dry load on Florisil) using the elution gradient EtOAc in Cyclohexane 0-100% to give tert-butyl (3-(3-amino-6- chloropyridin-2-yl)prop-2-yn-1-yl)carbamate (1.1635 g, 4.13 mmol, 86% yield) as a orange solid. LCMS (System B, UV, ESI): Rt = 0.96 min, [M+H]+ 282
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