反应详情

To a flask equipped with a magnetic stirrer, reflux condenser, and nitrogen inlet was added 2,3-dihydro-1-benzofuran-5-amine (4.53 grams, 33.3 mmoles, prepared as in Example 23 of U.S. Pat. No. 20040029932), 5-bromo-2,3-dihydrobenzofuran (6.63 grams, 32.9 mmoles), tris(dibenzylideneacetone)dipalladium (0) (0.61 grams, 0.67 mmoles), rac-2,2′-bis(diphenylphosphino)-1,1′-binapthyl (0.83 grams, 1.33 mmoles), sodium tert-butoxide (6.44 grams, 66.6 mmoles) and anhydrous toluene (60 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 (200 mL). The combined organic layers were concentrated in vacuo to yield a dark yellow oil. The solid was chromatographed on silica gel, eluting with a hexane/ethyl acetate gradient. The resulting solid was recrystallized from ethanol to afford 1.8 grams of the desired product as a white solid. 1H NMR (CDCl3/D2O) δ 6.55-6.95 (m, 6H), 4.5 (t, 4H), 3.15 (t, 4H).

1. customTo a flask equipped with a magnetic stirrer
2. temperaturereflux condenser, and nitrogen inlet
3. custom4.53 grams, 33.3 mmoles, prepared as in Example 23 of U.S
4. temperatureThe contents of the flask were refluxed for three days
5. filtrationand filtered through a pad of silica gel
6. washThe silica gel pad was then eluted with dichloromethane (200 mL)
7. concentrationThe combined organic layers were concentrated in vacuo
8. customto yield a dark yellow oil
9. customThe solid was chromatographed on silica gel
10. washeluting with a hexane/ethyl acetate gradient
11. customThe resulting solid was recrystallized from ethanol