反应详情

t-Butyl lithium (8.0 cm3 of a 2.0M solution in pentane) was added dropwise to a stirred solution of 6-bromo-2-methoxy-8 -methylquinoline (2.0 g) in THF (20 cm3) at -70° under nitrogen. After 10 minutes the mixtures was treated with a solution of anhydrous zinc chloride (1.09 g) in THF (10 cm3) and the resulting solution was warmed to 0°. A solution containing 3-bromopyridine (1.26 g) and tetrakis(triphenylphosphine) palladium(O) (0.05 g) in THF (10 cm3) was then added and the mixture was heated under reflux for 2 hours. The reaction mixture was cooled, concentrated in vacuo, treated with chloroform (100 cm3) and a solution of ethylenediaminetetraacetic acid disodium salt (6 g) in water (100 cm3). The aqueous phase was extracted further with chloroform (3×50 cm3) and the combined and dried (MgSO4) extracts were concentrated in vacuo to give an oil. This oil was chromatographed on silica (Merck "MK 60.9385") eluting with ethyl acetate. The fractions containing the product were combined and evaporated to afford a solid which was recrystallised from hexane to afford 2-methoxy-8-methyl-6-(3-pyridyl)quinoline, m.p. 117°-118.5°, (1.12 g).

1. temperaturethe resulting solution was warmed to 0°
2. additionwas then added
3. temperaturethe mixture was heated
4. temperatureunder reflux for 2 hours
5. temperatureThe reaction mixture was cooled
6. concentrationconcentrated in vacuo
7. additiontreated with chloroform (100 cm3)
8. extractionThe aqueous phase was extracted further with chloroform (3×50 cm3)
9. dry with materialdried (MgSO4) extracts
10. concentrationwere concentrated in vacuo
11. customto give an oil
12. customThis oil was chromatographed on silica (Merck "MK 60.9385")
13. washeluting with ethyl acetate
14. additionThe fractions containing the product
15. customevaporated
16. customto afford a solid which
17. customwas recrystallised from hexane