Hydrochloric Acid → 1-(5-Bromo-4-methyl(2-pyridyl))-2,2,2-trifluoroethylamine

To a solution of 1-(5-bromo-4-methylpyridin-2-yl)-2,2,2-trifluoro-N-(4-methoxybenzylidene)ethanamine (77 mg; 0.1989 mmol) in dioxane (1.0 mL; 12 mmol) was added a 1 mol/L solution of hydrochloric acid in water (1.0 mL; 1.0 mmol). The reaction mixture was stirred at room temperature for 2 hours and then heated at 60° C. for 4 hours. The reaction mixture was partitioned between ethyl acetate and water. The layers were separated, and the aqueous layer adjusted to pH 7 with saturated aqueous sodium bicarbonate. The aqueous layer was extracted twice with dichloromethane. The combined dichloromethane extracts were dried over magnesium sulfate, filtered, and concentrated to yield 33.3 mg (62%) of the title compound, which was carried forward without purification. LCMS (ESI): M+H=269.2; 1H NMR (400 MHz, DMSO) δ 8.67 (s, 1H), 7.59 (s, 1H), 4.54 (dd, J=15.9, 7.9 Hz, 1H), 2.55 (d, J=7.8 Hz, 2H), 2.39 (s, 3H).

1. temperatureheated at 60° C. for 4 hours
2. customThe reaction mixture was partitioned between ethyl acetate and water
3. customThe layers were separated
4. extractionThe aqueous layer was extracted twice with dichloromethane
5. dry with materialThe combined dichloromethane extracts were dried over magnesium sulfate
6. filtrationfiltered
7. concentrationconcentrated

ORD record

ord-91b76e7a30f74286b7c5c8f372241a42

Source dataset

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09206175B2