Iodine → HCID 59320162, compound

Temperature

-78 °C

To a solution of tert-butyl [1-(6,8-difluoro[1,2,4]triazolo[4,3-a]pyridin-3-yl)-1-methylethyl]carbamate (1.32 g, 4.23 mmol) in tetrahydrofuran (20 mL) under argon atmosphere and at −78° C. was slowly added LiHMDS (1M in hexanes, 9.3 mL, 9.3 mmol). It was stirred at −78° C. for 45 min, afterwards a solution of iodine (1.13 g, 4.44 mmol) in tetrahydrofuran (10 mL) was added dropwise. The resulting mixture was stirred at −78° C. for 2 hours, warmed to 0° C. and diluted with aqueous sodium bisulphite (10 mL) and saturated ammonia chloride (10 mL). It was warmed to room temperature, extracted with ethyl acetate, dried over anhydrous sodium sulphate and concentrated under reduced pressure. The crude was purified by silica flash chromatography eluting with hexanes/ethyl acetate, using a gradient from 50% to 83% of ethyl acetate to yield the title compound (0.979 g, 53%) as a yellow solid.

1. customat −78° C.
2. stirringThe resulting mixture was stirred at −78° C. for 2 hours
3. temperaturewarmed to 0° C.
4. temperatureIt was warmed to room temperature
5. extractionextracted with ethyl acetate
6. dry with materialdried over anhydrous sodium sulphate
7. concentrationconcentrated under reduced pressure
8. customThe crude was purified by silica flash chromatography
9. washeluting with hexanes/ethyl acetate

ORD record

ord-68165f9aa47a409caca2147eafe93aed

Source dataset

uspto-grants-2012_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08258122B2