反应详情

温度

100 °C

Combine 1-[4-(3-amino-benzyloxy)-2-hydroxy-3-propyl-phenyl]-ethanone (1.65 g, 5.51 mmol), 3-bromo-benzonitrile (912 mg, 5.01 mmol), cesium carbonate (2.29 g, 7.01 mmol), and 18-crown-6 (132 mg, 0.501 mmol) in toluene (25 mL) and stir. Purge reaction vessel with argon. Add BINAP [rac-2,2′-bis(diphenyl-phosphino)-1,1′-binaphthyl] (468 mg, 0.752 mmol), and palladium acetate (112 mg, 0.501 mmol). Purge reaction vessel with argon. Heat to 100° C. for 18 hours and cool to ambient temperature. Add 10% aqueous citric acid, and extract with ethyl acetate. Combine the organic layers, dry with sodium sulfate, filter and concentrate to dryness. Purify the resulting residue by flash chromatography eluting with 30% ethyl acetate:hexanes to yield a yellow oil (1.36 g, 68%): 1H NMR (CDCl3) δ 0.92 (t, 3H), 1.56 (sextet, 2H), 2.56 (s, 3H), 2.69 (t, 2H), 5.15 (s, 2H), 5.86 (bs, 1H), 6.49 (d, 1H), 7.06 (m, 2H), 7.15-7.21 (m, 3H), 7.27-7.37 (m, 3H), 7.59 (d, 1H), 12.75 (s, 1H).

1. customPurge
2. customreaction vessel with argon
3. customPurge
4. customreaction vessel with argon
5. temperaturecool to ambient temperature
6. extractionextract with ethyl acetate
7. dry with materialdry with sodium sulfate
8. filtrationfilter
9. concentrationconcentrate to dryness
10. customPurify the resulting residue by flash chromatography
11. washeluting with 30% ethyl acetate