Reaktion #360430

Reaktionsgleichung

NH3

product

7-Bromo-4-chloro-3-(2-chloro-ethyl)-cinnoline

4-cyanophenylboronic acid

Na2CO3

→

4-[3-(2-Chloro-ethyl)-cinnolin-7-yl]-benzonitrile

Ausbeute 50.0%

Lösungsmittel

water

isopropanol toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturAfter cooling
2. 2
   Extraktionextracted twice with 25 mL dichloromethane
3. 3
   Einengenconcentrated under reduced pressure
4. 4
   SonstigeThe crude material was purified by column chromatography (1000% dichloromethane to 99:1 dichloromethane/methanol)
5. 5
   Sonstigeto afford the product in 50% yield as a brown-orange solid

Vorschrift

A mixture of the product from Example 169C (0.095 g, 0.312 mmol), 4-cyanophenylboronic acid (0.046 g, 0.343 mmol), Pd(PPh3)2Cl2 (0.011 g, 0.016 mmol), and 1 M Na2CO3 (0.778 mL, 0.778 mmol) in de-gassed isopropanol/toluene (5 mL, 1:1) was heated to 90° C. under a dry nitrogen atmosphere for 24 hours. After cooling, the reaction mixture was diluted with 20 mL water, extracted twice with 25 mL dichloromethane, and concentrated under reduced pressure. The crude material was purified by column chromatography (1000% dichloromethane to 99:1 dichloromethane/methanol) to afford the product in 50% yield as a brown-orange solid. 1H NMR (CDCl3, 300 MHz) δ 8.76 (d, J=3 Hz, 1H), 8.02 (dd, J=3, 9 Hz, 1H), 7.96 (d, J=9 Hz, 1H), 7.87 (q, J=9 Hz, 4H), 7.80 (s, 1H), 4.14 (t, J=6 Hz, 2H), 3.69 (t, J=6 Hz, 2H). MS (DCl—NH3) [M−Cl]+ at 258, [M+H]+ at 294.

Quelle