Methyl iodide → Pyridine, 3-bromo-2-methoxy-6-(methoxymethyl)-

Temperature

0 °C

step 1—A NaH dispersion (226 mg, 5.64 mmol, 60% mineral oil dispersion) was triturated with hexanes (3×10 mL) and dried under a stream of N2 then suspended in THF (23.5 mL) and cooled to 0° C. A solution of 3-bromo-2-methoxy-6-(hydroxymethyl)pyridine (0.88 g, 3.79 mmol) in THF (10 mL) was added drop-wise and the mixture was stirred for 30 min. To the solution was added MeI (1.00 g, 441 μl, 7.05 mmol) and the mixture was warmed to RT. After 1 h the crude reaction mixture was concentrated in vacuo and the mixture was poured into H2O (100 mL) and extracted with EtOAc (3×50 mL). The combined extracts were washed sequentially with H2O, brine, dried, filtered and concentrated to afford 3-bromo-2-methoxy-6-methoxymethyl-pyridine (136) as a light yellow oil.

1. customstep 1—A NaH dispersion (226 mg, 5.64 mmol, 60% mineral oil dispersion) was triturated with hexanes (3×10 mL)
2. dry with materialdried under a stream of N2
3. temperaturethe mixture was warmed to RT
4. customAfter 1 h the crude reaction mixture
5. concentrationwas concentrated in vacuo
6. additionthe mixture was poured into H2O (100 mL)
7. extractionextracted with EtOAc (3×50 mL)
8. washThe combined extracts were washed sequentially with H2O, brine
9. customdried
10. filtrationfiltered
11. concentrationconcentrated

ORD record

ord-93342754ce304d30856e84890a4e0570

Source dataset

uspto-grants-2013_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08487103B2