Dimethyl Sulfide → HCID 70977600, compound

To a mixture of copper iodide (1.082 g, 0.0056 mol), dimethyl sulphide (2.78 mL, 0.0380 mol) and 3-bromo-5-methylpyridine (1.0 g, 0.0056 mol) in anhydrous tetrahydrofuran (25 mL) at room temperature was added phenyl chloroformate (0.764 mL, 0.0060 mol) and the mixture was stirred for 40-50 min. To this suspension at −25 to −20° C. was added cyclopropyl magnesium bromide (12.13 mL, 0.0060 mol, 0.5M solution in tetrahydrofuran) over 30-40 min. The mixture was stirred at this temperature for 30 min. and then warmed slowly to room temperature over 1.0-1.5 h. The reaction mixture was quenched with 20% ammonium chloride (25 mL), followed by extraction of the aqueous layer with ethyl acetate (50 mL). The organic layer was washed with 20% ammonium chloride (25 mL), then saturated aqueous sodium chloride solution (25 mL), and dried over anhydrous sodium sulphate. Silica gel chromatography using 0-5% ethyl acetate-hexane gradient yielded crude title compound.

1. stirringThe mixture was stirred at this temperature for 30 min.
2. customThe reaction mixture was quenched with 20% ammonium chloride (25 mL)
3. extractionfollowed by extraction of the aqueous layer with ethyl acetate (50 mL)
4. washThe organic layer was washed with 20% ammonium chloride (25 mL)
5. dry with materialsaturated aqueous sodium chloride solution (25 mL), and dried over anhydrous sodium sulphate

ORD record

ord-3d9e2dc40e8340a7a64755f103b66c3e

Source dataset

uspto-grants-2015_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09073929B2