HCID 44185545, compound → 5-[1-(Methylthio)ethyl]-2-trifluoromethylpyridine

Temperature

240 °C

To a dry 50 mL round bottom flask equipped with magnetic stirrer, nitrogen inlet, thermometer, and reflux condenser was charged 0.35 g (0.00132 moles) of 5-(1-methylthioethyl)-2-trifluoromethylnicotinic acid, 0.17 g (0.00264 moles) of copper powder and 10 mL of DowTherm A. The reaction was heated at 240° C. for 1 hour, then cooled to room temperature. The reaction mixture was extracted with 3 aliquots of 50 mL of ethyl acetate, and washed with 50 mL of water and 50 mL of saturated aqueous sodium chloride solution. The organic extract was dried over anhydrous magnesium sulfate, filtered, and concentrated under vacuum on a rotary evaporator. The crude product thus obtained was chromatographed on silica gel with a gradient of 100% hexane to 50% ethyl acetate, 50% hexane. The pure fractions were combined, and concentrated under vacuum on a rotary evaporator to afford 0.13 g of the title compound as a pale yellow oil. 1H NMR (CDCl3): δ 1.62 (d, 3H), 1.94 (s, 3H), 3.93 (q, 1H), 7.68 (d, 1H), 7.90 (d, 1H), and 8.66 (s, 1H).

1. customTo a dry 50 mL round bottom flask equipped with magnetic stirrer, nitrogen inlet
2. temperaturethermometer, and reflux condenser
3. temperaturecooled to room temperature
4. extractionThe reaction mixture was extracted with 3 aliquots of 50 mL of ethyl acetate
5. washwashed with 50 mL of water and 50 mL of saturated aqueous sodium chloride solution
6. extractionThe organic extract
7. dry with materialwas dried over anhydrous magnesium sulfate
8. filtrationfiltered
9. concentrationconcentrated under vacuum on a rotary evaporator
10. customThe crude product thus obtained
11. customwas chromatographed on silica gel with a gradient of 100% hexane to 50% ethyl acetate, 50% hexane
12. concentrationconcentrated under vacuum on a rotary evaporator

ORD record

ord-42d6c67c22cc49c4988e34e9247042cd

Source dataset

uspto-grants-2012_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08318946B2