Sodium methanethiolate → 5-Bromo-2-methylsulfanylmethyl-pyridine

Temperature

0 °C

To the stirred solution of 5-Bromo-2-chloromethyl-pyridine (3.5 gm, 16.99 mmol) in DMF (25 mL) at 0° C. is added Sodium thiomethoxide (1.31 gm, 18.68 mmol) resulting reaction mixture is stirred at 0° C. for 2 h. After completion quenched with water and extracted with ethyl acetate (3×100 mL). The Combined organic layer is washed with brine and organic layer dried over sodium sulphate, evaporate under reduced pressure. The crude is purified by column chromatography using silica 100-200 mesh using 10% EtOAc: Hexane as eluent to afford title compound (3 g) as brown colored liquid. 1NMR (400 MHz, DMSO) δ: 2.00 (s, 3H), 3.75 (s, 2H), 7.39 (d, J=8.32 Hz, 1H), 7.99-8.02 (dd, J1=2.44 Hz, J2=8.32 Hz, 1H), 8.60 (d, J=2.28 Hz, 1H). LC-MS (m/z): M+H=220.1.

1. customresulting
2. customreaction mixture
3. customAfter completion quenched with water
4. extractionextracted with ethyl acetate (3×100 mL)
5. washThe Combined organic layer is washed with brine and organic layer
6. dry with materialdried over sodium sulphate
7. customevaporate under reduced pressure
8. customThe crude is purified by column chromatography

ORD record

ord-d131c5f4e7c041d196a4c2ed5a1a6949

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09422236B2