Methyl iodide → 2-(1-Methoxy-1-methyl-ethyl)-4-tributylstannanyl-pyridine

A solution of 2-(4-tributylstannanyl-pyridin-2-yl)-propan-2-ol 12AO (0.12 g, 0.27 mmol) in THF (2 ml) was added in a dry NaH (0.02 g, 0.54 mmol). Reaction mixture was stirred for 20 min at r.t. It was cooled to 0° C. and CH3I (0.02 ml, 0.32 mmol) was added drop wise. After 30 mins at 0° C., reaction mixture was warmed up to r.t. It was diluted with EtOAc (15 ml) after 2 hr and washed with water (2×3 ml) and brine (5 ml). Organic extracts were dried over MgSO4, filtered and concentrated. The residue was purified on silica gel eluting with 1/4 EtOAc/Hexane to give the desired product 2-(1-methoxy-1-methyl-ethyl)-4-tributylstannanyl-pyridine 13AO (0.1 g, 88%).

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

ORD record

ord-5eba0317a573493bab3dde349a172398

Source dataset

uspto-grants-2013_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08546404B2