Isopropanol → 2-Bromo-6-isopropoxypyridine

Temperature

80 °C

The compound was prepared in a manner similar to that described in WO 02/076983 (page 80). Dry isopropanol (25 mL, 42.2 mmole) was placed in an oven-dried 250 ml 3 necked flask under nitrogen, sodium spheres (0.5 g, 21.1 mmol) were added and the reaction was heated to 80° C. to dissolve the sodium. 2,6 dibromopyridine (10 g, 42.2 mmole) was added as a solid and the reaction was heated at 95° C. After heating for ˜2.5 hr the reaction was cooled and partitioned between ether and water. The organic layer was evaporated to give a solid plus oil, the mixture was suspended in hexanes, cooled, and filtered to remove the solid. The filtrate was evaporated carefully and chromatographed on silica eluting with hexanes to give the product as a clear, colorless oil.

1. customThe compound was prepared in a manner similar to
2. additionwere added
3. temperaturethe reaction was heated at 95° C
4. temperatureAfter heating for ˜2.5 hr the reaction
5. temperaturewas cooled
6. custompartitioned between ether and water
7. customThe organic layer was evaporated
8. customto give a solid plus oil
9. temperaturecooled
10. filtrationfiltered
11. customto remove the solid
12. customThe filtrate was evaporated carefully
13. customchromatographed on silica eluting with hexanes
14. customto give the product as a clear, colorless oil

ORD record

ord-e8cfb4d91af94cd18d3c56cc6cd6a1b1

Source dataset

uspto-grants-2012_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08114887B2