Methyl iodide → 4-Iodo-2-methoxymethyl-pyridine

A solution of (4-iodo-pyridin-2-yl)-methanol 6AN (0.51 g, 2.16 mmol) in THF (7.5 ml) was added in a dry NaH (0.17 g, 4.32 mmol). Reaction mixture was stirred for 20 min at r.t. It was cooled to 0° C. and CH3I 0.16 ml, 2.59 mmol) was added drop wise. After 30 mins at 0° C., it was warmed up to r.t. and stirred further for 2 hr. Then it was diluted with EtOAc (50 ml) and washed with water (2×10 ml) and brine (1×15 ml). Organic extracts were dried over MgSO4, filtered and concentrated. The residue was purified on silica gel eluting with 1/2 EtOAc/Hexane to give the desired product 4-Iodo-2-methoxymethyl-pyridine 7AN (0.39, 72%).

1. customReaction mixture
2. temperatureIt was cooled to 0° C.
3. waitAfter 30 mins at 0° C.
4. temperatureit was warmed up to r.t.
5. stirringstirred further for 2 hr
6. washwashed with water (2×10 ml) and brine (1×15 ml)
7. dry with materialOrganic extracts were dried over MgSO4
8. filtrationfiltered
9. concentrationconcentrated
10. customThe residue was purified on silica gel eluting with 1/2 EtOAc/Hexane

ORD record

ord-e013e023cde54c468319cc85a84e7e5b

Source dataset

uspto-grants-2013_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08546404B2