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copper(II) sulfate; In dichloromethane; at 20℃; for 17h;
Intermediate 44: (S)-(3-Methylpyridin-2-yl)(4-(trifluoromethyl)phenyl)- methanamine hydrochlorid Step 1. (S^-l-Methyl-N-iiS-methylpyridin-l-ylJmethyleneipropane-l- sulflnamideTo a solution of <strong>[55589-47-4]3-methyl-2-pyridinecarboxaldehyde</strong> (3.243 g, 26.8 mmol) in DCM (18 mL) was added (S)-2-methylpropane-2-sulfinamide (6.55 g, 54.0 mmol) and copper(II) sulfate (8.72 g, 54.6 mmol). The suspension was stirred at rt for 17 hours, filtered, and the solid was washed with DCM (2 x 35 mL). The filtrates were concentrated, and the resulting product was purified by silica gel flash column chromatography (using a 80G ISCO cartridge) and eluted using DCM / MeOH gradient to yield the desired product (S,E)-2-methyl-N-((3- methylpyridin-2-yl)methylene)propane-2-sulfinamide as a yellow solid.
980 mg
With copper(II) sulfate; In dichloromethane; at 20℃; for 2h;
3-Methyl-2-pyridinecarbaldehyde (0.750 mL, 6.69 mmol, Sigma- Aldrich, St. Louis, MO) was added to a solution of (S)-2-methylpropane-2- sulfmamide (1.14 g, 9.36 mmol, AK Scientific, Mountain View, CA) and copper(II) sulfate (3.20 g, 20.1 mmol) in DCM (50 mL) and the mixture was stirred at room temperature for 2 h. The mixture was filtered, the filter residue was washed with DCM (30 mL), and the combined filtrate and washing were concentrated under reduced pressure. The residue was purified by flash chromatography (100 g of silica gel, 33percent EtOAc/hexanes) to afford (S)-N-((1E)- (3-methyl-2-pyridinyl)methylidene)-2-methyl-2-propanesulfinamide (980 mg) as a light-yellow solid.
(S,E)-N-((2-bromopyridin-4-yl)methylene)-2-methylpropane-2-sulfinamide[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
With titanium(IV) tetraethanolate; In tetrahydrofuran; at 35℃; for 1h;Inert atmosphere;
To a mixture of 2-bromoisonicotinaldehyde (68.0 g, 365 mmol) and compound (S)-2-methylpropane-2-sulfinamide (48.7 g, 402 mmol) in THF (400 mL) was added Ti(OEt)4 (125 g, 548 mmol, 113 mL) in one portion at 20 C. under N2. The mixture was stirred at 35 C. for 1 h. Water (200 mL) and EtOAc (200 mL) was added into the mixture, and stirred for 5 min. The mixture was filtered, and the filtered cake was washed with EtOAc (200 mL). The combined organic layers were washed with water (200 mL) and brine (200 mL), dried over anhydrous Na2SO4 and concentrated in vacuoto give compound (S,E)-N-((2-bromopyridin-4-yl)methylene)-2-methylpropane-2-sulfinamide (90.0 g, crude) as a yellow solid.
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