反应详情

To a flask equipped with a magnetic stirrer, reflux condensor, and nitrogen inlet was added 8-aminoquinoline (4.2 grams, 29.0 mmoles), 6-bromoquinoline (6.0 grams, 29.0 mmoles), tris(dibenzylideneacetone)dipalladium (0) (0.4 grams, 0.48 mmoles), rac-2,2′-bis(diphenylphosphino)-1,1′-binapthyl (0.6 grams, 0.60 mmoles), sodium tert-butoxide (4.7 grams, 49.0 mmoles) and anhydrous toluene (80 mL). The contents of the flask were refluxed for three days; cooled to room temperature; and filtered through a pad of silica gel. The silica gel pad was then eluted with dichloromethane (60 mL) and ethyl acetate (60 mL). The combined organic layers were concentrated in vacuo to yield a yellow solid. The solid was chromatographed on silica gel, eluting with a hexane/ethyl acetate gradient to afford 4.4 grams of the desired product as a yellow solid. 1H NMR (CDCl3) δ 8.8 (d, 2H), 8.6 (bs, 1H), 8.0-8.2 (m, 3H), 7.2-7.8 (m, 7H).

1. customTo a flask equipped with a magnetic stirrer
2. temperaturereflux condensor, and nitrogen inlet
3. temperatureThe contents of the flask were refluxed for three days
4. filtrationand filtered through a pad of silica gel
5. washThe silica gel pad was then eluted with dichloromethane (60 mL) and ethyl acetate (60 mL)
6. concentrationThe combined organic layers were concentrated in vacuo
7. customto yield a yellow solid
8. customThe solid was chromatographed on silica gel
9. washeluting with a hexane/ethyl acetate gradient