Reaktion #76327

Reaktionsgleichung

(3-phenoxyphenyl) [[(2′-(trifluoromethyl)[1,1′-biphenyl]-3-yl]methyl]amino]-1,1,1-tri-fluoro-2-propanol

K2CO3

3-[(3-phenoxyphenyl)[[3-bromophenyl]methyl]-amino]-1,1,1-trifluoro-2-propanol

2-(tri-fluoromethyl)phenylboronic acid

→

3-[(3-phenoxyphenyl)[[2′-(trifluoromethyl)[1,1′-biphenyl]-3-yl]methyl]amino]-1,1,1-trifluoro-2-propanol

Lösungsmittel

EtOH

water

DMF

toluene

EtOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe slurry was heated
2. 2
   Temperaturto reflux under argon for 18 h
3. 3
   Extraktionextracted with ethyl acetate
4. 4
   WaschenThe organic layer was washed with brine
5. 5
   Trocknendried (MgSO4)
6. 6
   Sonstigeevaporated to an oil
7. 7
   SonstigePurification by flash chromatography on silica gel eluting with 20% ethyl acetate in hexane
8. 8
   Sonstigegave an oil which
9. 9
   Sonstigedried in vacuo
10. 10
    Sonstigeto give 0.32 g (55%) of the

Vorschrift

To a toluene (8 mL) solution of 3-[(3-phenoxyphenyl)[[3-bromophenyl]methyl]-amino]-1,1,1-trifluoro-2-propanol (0.51 g, 1.1 mmol) from EX-595B was added 2-(tri-fluoromethyl)phenylboronic acid (0.33 g, 1.7 mmol) and DMF (3 mL). To the resulting solution was added K2CO3 (0.31 g, 2.2 mmol) and Pd(PPh3)4 (0.060 g, 0.05 mmol). The slurry was heated to reflux under argon for 18 h. The cooled mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with brine, dried (MgSO4) and evaporated to an oil. Purification by flash chromatography on silica gel eluting with 20% ethyl acetate in hexane gave an oil which was dissolved in EtOH, stripped and dried in vacuo to give 0.32 g (55%) of the desired 3-[(3-phenoxyphenyl) [[(2′-(trifluoromethyl)[1,1′-biphenyl]-3-yl]methyl]amino]-1,1,1-tri-fluoro-2-propanol product as a colorless oil. Anal. calcd. for C29H23NO2F6.0.8 EtOH: C, 64.67; H, 4.93; N, 2.46. Found: C, 64.53; H, 4.69; N, 2.49. HRMS calcd. 532.1711 [M+H]+, found: 532.1708. 1H NMR (C6D6) δ1.72 (d, 11H), 3.17 (dd, 11H), 3.46 (dd, 11H), 3.72 (m, 1H), 4.23 (s, 2H), 6.33 (dd, 1H), 6.43 (dd, 1H), 6.52 (t, 1H), 6.82 (m, 2H), 6.9-7.1 (m, 11H), 7.43 (d, 11H).

Quelle