Reaktion #304326

Reaktionsgleichung

4-bromo-2-nitroaniline

pyridine-3-boronic acid 1,3-propanediol cyclic ester

sodium bicarbonate

→

title compound

Ausbeute 105.6%

4-(Pyridin-3-yl)-2-nitroaniline

Ausbeute 105.6%

Lösungsmittel

DME

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthen cooled to room temperature
2. 2
   SonstigeThe solids were collected
3. 3
   Waschenwashed with water, 5% EtOAc in Hexane
4. 4
   Sonstigedried

Vorschrift

To a solution of 4-bromo-2-nitroaniline (4.8 g, 22 mmol) in DME (100 mL) was added pyridine-3-boronic acid 1,3-propanediol cyclic ester (4 g, 24 mmol), sodium bicarbonate (45 mL, 1M), and tetrakis(triphenylphosphine)palladium (0.05 eq). The resulting mixture was heated at 90° C. for 8 hours then cooled to room temperature. The solids were collected, washed with water, 5% EtOAc in Hexane and dried to afford the title compound (5 g). 1H NMR (CDCl3) δ 8.8 (d, 1H), 8.55 (m, 1H), 8.35 (d, 1H), 7.85 (dd, 1H), 7.65 (dd, 1H), 7.35 (m, 1H), 6.95 (d, 1H), 6.25 (br s, 2H).

Quelle