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N-(dihydrofuran-3(2H)-ylidene)-2-methylpropane-2-sulfinamide[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
With titanium(IV) tetraethanolate; In tetrahydrofuran; at 20 - 60℃; for 8h;Inert atmosphere;
Intermediate 334A: N-(Dihydrofuran-3(2H)-ylidene)-2-methylpropane-2-sulfinamide To a stirred solution of <strong>[22929-52-8]dihydrofuran-3(2H)-one</strong> (0.901 mL, 11.62 mmol) in THF (20 mL) at RT under nitrogen was added Ti(OEt)4 (4.87 mL, 23.23 mmol), 2-methylpropane-2-sulfinamide (1.549 g, 12.78 mmol) and the reaction mixture was stirred at 60 C. for 8 h. The reaction mixture was quenched with a saturated aq. solution of NaHCO3 with vigorous stirring. The precipitate was filtered and washed with EtOAc and the aq. layer was extracted with EtOAc. The combined organic layer was dried over sodium sulfate, filtered and concentrated. The crude product was purified by silica gel chromatography (40 g REDISEP column, eluting with 25% ethyl acetate in hexanes). Fractions containing the product were combined and evaporated to afford Compound 334A as a pale yellow liquid (700 mg, 32%). The crude compound was taken to next step without purification.
With titanium(IV) isopropylate; In tetrahydrofuran; at 60℃;
A solution of <strong>[22929-52-8]dihydrofuran-3(2H)-one</strong> (300 mg, 3.48 mmol), 2-methylpropane-2- sulfinamide (422 mg, 3.48 mmol), and titanium(IV) isopropoxide (1.07 ml, 3.66 mmol) in THF (5 ml) was heated to 60 C overnight. The reaction mixture was cooled to room temperature, diluted with EtOAc, and poured into brine. The suspension was filtered and the layers were separated. The organic layer was dried over MgS04, filtered, and concentrated. The residue was used without purification. LCMS calculated for CgHi6N02S (M+H)+: m/z = 190.1, found: 190.1.
N-((4-chloro-3-fluoropyridin-2-yl)methyl)-2-methylpropane-2-sulfinamide[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
With sodium tetrahydroborate; caesium carbonate;
Synthesis of N-((4-chloro-3-fluoropyridin-2-yl)methyl)-2-methylpropane-2-sulfinamide. To a solution of <strong>[1260878-78-1]4-chloro-3-fluoropicolinaldehyde</strong> (26.0 g, mixtutre, 163.0 mmol) in DCM (100 mL) was added cesium carbonate (96.0 g, 293.3 mmol) and 2-methylpropane-2-sulfinamide (19.8 g, 163.0 mmol) at RT. The reaction mixture was stirred for 3 h at RT. After the reaction was complete, the reaction mixture was filtrated and washed with DCM three times. To the combined mixture was added MeOH (40 mL), and then the resulting mixture was cooled to 0 C. by ice-water bath. Sodium borohydride (15.5 g, 409.0 mmol) was added slowly in portions. The reaction mixture was warmed up to RT and stirred at this temperature for 2 h. The reaction was quenched with H2O carefully. The resulting mixture was extracted with DCM (100 mL*3), the combined organic solvent was dried by sodium sulfate, filtered, and concentrated to get crude N-((4-chloro-3-fluoropyridin-2-yl)methyl)-2-methylpropane-2-sulfinamide (43.3 g, crude) as yellow solid. ESI-MS [M+H]+: 265.1.
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