Iodine → HCID 60026403, compound

Temperature

-78 °C

A solution of 4-[(tert-butoxycarbonyl)amino]-2-methoxypyridine (1.8 g, 8.03 mmol, 1.0 equiv) in 100 mL of anhydrous diethyl ether was treated with 2.79 mL of N,N,N′,N′-tetramethylethylenediamine (18.5 mmol, 2.3 equiv) under an inert atmosphere. The resulting solution was cooled to −78° C., treated with n-BuLi (2.5 M, 7.2 mL, 18.0 mmol, 2.24 equiv) and warmed to −7° C. The reaction was stirred at −7° C. to 0° C. for 3 hours, cooled to −78° C. and treated with a solution of iodine (3.05 g, 12 mmol) in 30 mL of anhydrous THF. The resulting mixture was stirred to room temperature for 16 hours. 200 mL of saturated ammonium chloride solution and 100 mL of diethyl ether were added. The phases were separated and the organic layer was washed with 100 mL of sodium thiosulfate (10% aqueous solution), dried over sodium sulfate, decanted, and concentrated in vacuo. Chromatography on SiO2 (100% dichloromethane to 5% methanol in dichloromethane, gradient) provided the title product (650 mg, 23% yield) as a white wax.

1. temperaturewarmed to −7° C
2. temperaturecooled to −78° C.
3. stirringThe resulting mixture was stirred to room temperature for 16 hours
4. customThe phases were separated
5. washthe organic layer was washed with 100 mL of sodium thiosulfate (10% aqueous solution)
6. dry with materialdried over sodium sulfate
7. customdecanted
8. concentrationconcentrated in vacuo

ORD record

ord-7d14f6ec8ca544f5ba916ec4801e8be6

Source dataset

uspto-grants-2014_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08741897B2