Реакция #78759

Уравнение реакции

(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

Растворители

EtOH

water

DMF

toluene

EtOH

Условия реакции

Обработка

1. 1
   ТемператураThe slurry was heated
2. 2
   Температураto reflux under argon for 18 h
3. 3
   Экстракцияextracted with ethyl acetate
4. 4
   ПромывкаThe organic layer was washed with brine
5. 5
   Сушкаdried (MgSO4)
6. 6
   Другоеevaporated to an oil
7. 7
   ДругоеPurification by flash chromatography on silica gel eluting with 20% ethyl acetate in hexane
8. 8
   Другоеgave an oil which
9. 9
   Другоеdried in vacuo
10. 10
    Другоеto give 0.32 g (55%) of the

Методика

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) δ 1.72 (d, 1H), 3.17 (dd, 1H), 3.46 (dd, 1H), 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, 1H).

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