Iodine → HCID 86607565, compound

Temperature

-78 °C

A solution of 6-Methyl-pyridine-2-carboxylic acid-(3-chloro-phenyl)-amide (1.96 g, 7.9 mmol) in THF (20.0 ml) was cooled to −78° C. A 1.6 M solution of n-BuLi in hexane (11.0 ml, 17.6 mmol, 2.2 equiv.) was added dropwise and the reaction was stirred for 30 min at −78° C. A solution of 2.02 g (7.9 mmol) of iodine in THF (20.0 ml) was added dropwise maintaining the temperature below −75° C. After 5 min, the reaction mixture was allowed to warm up to r.t. The mixture was quenched by the addition of sat. ammonium sulfate soln. (5 ml) and 40% sodium hydrogensulfite solution (5 ml). The pH of the solution was adjusted to 8 by the addition of sat. bicarbonate soln. The mixture was then extracted twice with ethyl acetate. The combined organic phases were washed with water, dried over magnesium sulfate and concentrated in vaccuo. The dark brown residue (2.66 g) was purified by flash chromatography (heptane/ethyl acetate 9:1) to yield a the title compound as a beige solid (total 1.42 g, 48%), MS (ISP): m/e=373.0, 375.0 (M+H+).

1. temperaturemaintaining the temperature below −75° C
2. waitAfter 5 min
3. temperatureto warm up to r.t
4. customThe mixture was quenched by the addition of sat. ammonium sulfate soln
5. additionThe pH of the solution was adjusted to 8 by the addition of sat. bicarbonate soln
6. extractionThe mixture was then extracted twice with ethyl acetate
7. washThe combined organic phases were washed with water
8. dry with materialdried over magnesium sulfate
9. concentrationconcentrated in vaccuo
10. customThe dark brown residue (2.66 g) was purified by flash chromatography (heptane/ethyl acetate 9:1)

ORD record

ord-52d6cb69ce1b48bc84e256c4284b23b9

Source dataset

uspto-grants-2008_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07414060B2