Methyl iodide → HCID 58674371, compound

Temperature

-78 °C

To a solution of 4-chloro-N-methylpyridine-2-carboxamide (0.700 g, 4.12 mmol) in THF was added LDA (4.12 mL, 2M in THF, 8.24 mmol) dropwise at −78° C. under an atmosphere of argon. The mixture was allowed to stir for 90 min at −78° C. and then methyl iodide (1.51 mL, 24.71 mmol) was added. After stirring for 90 min, the solution was allowed to warm to 0° C. The reaction was quenched at 0° C. with sat. sodium hydrogen sulfite and extracted with EtOAc. The combined organic solutions were washed with water, dried over MgSO4, filtered and concentrated. The residue was purified by column chromatography to give the desired product (0.070 g, 23%).

1. stirringAfter stirring for 90 min
2. temperatureto warm to 0° C
3. customThe reaction was quenched at 0° C. with sat. sodium hydrogen sulfite
4. extractionextracted with EtOAc
5. washThe combined organic solutions were washed with water
6. dry with materialdried over MgSO4
7. filtrationfiltered
8. concentrationconcentrated
9. customThe residue was purified by column chromatography

ORD record

ord-7ebc7c1248494dfca2c6b171c004c118

Source dataset

uspto-grants-2010_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07652041B2