Methyl iodide → 2-Fluoro-4-iodo-3-methylpyridine

Temperature

-78 °C

To a solution of LDA, freshly prepared from diisopropylamine (0.126 mL, 0.899 mmol) and n-BuLi (0.899 mmol), in THF (2 mL) at -78° C. is cannulated a solution of 2-fluoro-3-iodopyridine (200 mg, 0.897 mmol) in 0.4 mL of THF, and the mixture is stirred for 1 hour at -78° C. under nitrogen. Iodomethane (0.17 mL, 2.73 mmol) is added neat and the mixture is stirred for 30 min. at -78° C. The mixture is quenched with saturated sodium bicarbonate solution at -78° C. and then extracted with ether. Combined ether extracts are dried (MgSO4) and concentrated in vacuo. The residue is purified by radial plc (silica gel, hexanes) to give 154 mg (72%) of product as an off-white solid having amp of 90-91 ° C.

1. stirringthe mixture is stirred for 30 min. at -78° C
2. customThe mixture is quenched with saturated sodium bicarbonate solution at -78° C.
3. extractionextracted with ether
4. dry with materialCombined ether extracts are dried (MgSO4)
5. concentrationconcentrated in vacuo
6. customThe residue is purified by radial plc (silica gel, hexanes)

ORD record

ord-0cf09d6fca6949b88d8ed89fcd90412f

Source dataset

uspto-grants-1996_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05496952