Iodine → (4-Iodo-6-trifluoromethylpyridin-3-yl)carbamic acid tert-butyl ester

Temperature

-10 °C

A solution of (6-trifluoromethylpyridin-3-yl)carbamic acid tert-butyl ester (0.90 g, 3.43 mmol) and N,N,N′,N′-tetramethylethylenediamine (1.29 mL, 8.55 mmol) in 25 mL of anhydrous diethyl ether was cooled to −78° C. under an argon atmosphere. The resulting mixture was treated dropwise with n-BuLi (2.5 M in hexanes, 3.42 mL, 8.55 mmol) over 5 minutes, and the mixture was allowed to warm to −10° C. After 30 minutes, the mixture was cooled to −78° C. and a solution of I2 (1.14 g, 4.5 mmol) in 5 mL of anhydrous THF was added rapidly. The resulting mixture was warmed to room temperature, stirred for 1 hour, and quenched with 50 mL of water. The organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo. The crude mixture was purified on SiO2 (10% ethyl acetate in dichloromethane) to afford the title compound (150 mg, 11.3% yield).

1. temperaturethe mixture was cooled to −78° C.
2. temperatureThe resulting mixture was warmed to room temperature
3. customquenched with 50 mL of water
4. dry with materialThe organic layer was dried over sodium sulfate
5. filtrationfiltered
6. concentrationconcentrated in vacuo
7. customThe crude mixture was purified on SiO2 (10% ethyl acetate in dichloromethane)

ORD record

ord-4e8c30f0a9784eae9f042f490b17c303

Source dataset

uspto-grants-2014_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08741897B2