Methyl iodide → 5-bromo-2-(methoxymethyl)Pyridine

Temperature

60 °C

To a stirred solution of 5-bromo-2-(hydroxymethyl)pyridine (150 mg, 0.798 mmol) in THF (8 mL) under nitrogen at r.t. was added sodium hydride (60% dispersion in oil, 64 mg, 1.60 mmol). After 30 minutes iodomethane was added and the reaction mixture was heated to 60° C. for 3 h, then cooled to r.t. and concentrated in vacuo. The residue was partitioned between DCM (50 mL) and water (50 mL); the organic fraction was washed with brine (50 mL), dried (MgSO4), and concentrated in vacuo to give the title compound (70 mg, 65%) as 70% pure material. LCMS (ES+) 202.0 (M+H)+, RT 2.40 minutes (Method 1).

1. temperaturecooled to r.t.
2. concentrationconcentrated in vacuo
3. customThe residue was partitioned between DCM (50 mL) and water (50 mL)
4. washthe organic fraction was washed with brine (50 mL)
5. dry with materialdried (MgSO4)
6. concentrationconcentrated in vacuo

ORD record

ord-86074e2e6c134105a9677cb87d9ca856

Source dataset

uspto-grants-2012_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08242116B2