Methyl iodide → HCID 58042692, compound

Sodium hydride (0.61 g, 60% in mineral oil, 15.32 mmol) was added to a solution of (5-chloropyridin-2-yl)methanol (2 g, 13.93 mmol) in THF (50 mL) and stirred at room temperature until no further gas evolution was observed. Iodomethane (0.95 mL, 15.32 mmol) was injected slowly and the reaction was allowed to stir at room temperature for 18 hours. The reaction was concentrated in vacuo, acidified with 2N HCl in water (25 mL) and extracted with EtOAc (2×20 mL). The aqueous layer was collected, basified with potassium hydroxide and extracted with DCM (3×20 mL). The organic layers were combined, washed with water, dried over sodium sulfate and concentrated in vacuo to afford the title compound (2 g, 91%).

1. stirringto stir at room temperature for 18 hours
2. concentrationThe reaction was concentrated in vacuo
3. extractionextracted with EtOAc (2×20 mL)
4. customThe aqueous layer was collected
5. extractionextracted with DCM (3×20 mL)
6. washwashed with water
7. dry with materialdried over sodium sulfate
8. concentrationconcentrated in vacuo

ORD record

ord-aea0e7ace7cf4861b4ebc8432dab6469

Source dataset

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09328096B2