Reaktion #163237

Reaktionsgleichung

{4-[4-(5-bromo-pyridin-2-yl)-phenyl]-cyclohexyl}-acetic acid methyl ester

3-amino-6-trifluoromethyl pyridine

cesium carbonate

2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl

→

title compound

(4-{4-[5-(6-Trifluoromethyl-pyridin-3-ylamino)-pyridin-2-yl]-phenyl}-cyclohexyl)-acetic acid methyl ester

Lösungsmittel

toluene t-butanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe suspension was sparged with nitrogen for 10 min
2. 2
   Temperaturheating for 45 min
3. 3
   TemperaturThe reaction was cooled to room temperature
4. 4
   Sonstigepartitioned between ethyl acetate and water
5. 5
   WaschenThe organic extracts were washed with brine
6. 6
   Trocknendried over sodium sulphate
7. 7
   Einengenconcentrated in vacuo
8. 8
   SonstigePurification by silica gel chromatography

Vorschrift

A microwave vial was charged with {4-[4-(5-bromo-pyridin-2-yl)-phenyl]-cyclohexyl}-acetic acid methyl ester (3.4 g, 8.8 mmol, 1.0 equiv), 3-amino-6-trifluoromethyl pyridine (2.1 g, 13.1 mmol, 1.2 equiv), cesium carbonate (7.1 g, 21.9 mmol, 2.5 equiv), 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (X-Phos, 0.42 g, 0.88 mmol, 0.1 equiv) and palladium acetate (0.30 g, 0.44 mmol, 0.05 equiv) in 20 Ml of toluene/t-butanol (9:1). The suspension was sparged with nitrogen for 10 min, then heated to 150° C. under microwave heating for 45 min. The reaction was cooled to room temperature, partitioned between ethyl acetate and water. The organic extracts were washed with brine, then dried over sodium sulphate and concentrated in vacuo. Purification by silica gel chromatography afforded the title compound: 1H NMR (400 MHz, DMSO-d6) δ 1.10-1.21 (m, 1H) 1.51 (qd, J=12.72, 2.78 Hz, 2H) 1.70-1.87 (m, 5H) 2.26 (d, J=6.57 Hz, 2H) 2.50 (m, 1H) 3.61 (s, 3H) 7.33 (d, J=8.34 Hz, 2H) 7.65 (d, J=2.53 Hz, 1H) 7.67-7.74 (m, 2H) 7.89 (d, J=8.59 Hz, 1H) 7.95 (d, J=8.34 Hz, 2H) 8.46 (d, J=2.53 Hz, 1H) 8.54 (d, J=2.53 Hz, 1H) 9.18 (s, 1H); (M+H)+427.3.

Quelle