Sodium hydride → HCID 86664596, compound

To a stirred suspension of sodium hydride (765 mg, 60% dispersion in mineral oil) in dry diethyl ether (20 ml) under an argon atmosphere at 0° C. was added dropwise a solution of (RS)-1-(5-bromo-pyridin-2-yl)-2,2,2-trifluoro-ethanol (3.06 g) in diethyl ether (10 ml) and the resulting mixture was stirred at room temperature for 30 min. Trifluoromethanesulfonyl chloride (1.4 ml) was added and stirring was continued for a further 15 min at room temperature. The reaction mixture was quenched by addition of 10% aq. sodium bicarbonate solution and the mixture was extracted with diethyl ether. The phases were separated and the organic phase was washed with saturated brine. The organic phase was separated, dried over sodium sulphate, and concentrated in vacuo. The reside was purified by Kugelrohr distillation (60° C. oven temperature, 0.3 mbar) to give (RS)-trifluoro-methanesulfonic acid 1-(5-bromo-pyridin-2-yl)-2,2,2-trifluoro-ethyl ester (3.6 g, 78%) as a white solid. MS (EI): 389 ([{81Br}M]+), 387 ([{79Br}M]+), 320 ([{81Br}M−CF3]+), 318 ([{79Br}M−CF3]+), 256 ([{81Br}M−CF3—SO2]+), 254 ([{79Br}M−CF3—SO2]+), 240 ([{81Br}M−OSO2CF3]+), 238 ([{79Br}M−OSO2CF3]+).

1. stirringstirring
2. waitwas continued for a further 15 min at room temperature
3. customThe reaction mixture was quenched by addition of 10% aq. sodium bicarbonate solution
4. extractionthe mixture was extracted with diethyl ether
5. customThe phases were separated
6. washthe organic phase was washed with saturated brine
7. customThe organic phase was separated
8. dry with materialdried over sodium sulphate
9. concentrationconcentrated in vacuo
10. distillationThe reside was purified by Kugelrohr distillation (60° C. oven temperature, 0.3 mbar)

ORD record

ord-96b09e6b97fa40ee8f891965c5d9d2d8

Source dataset

uspto-grants-2014_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08673950B2