Cesium carbonate → HCID 4763938, compound

Participants

Reaction Conditions

Reaction Steps

4-bromobenzonitrile (218 mg, 1.2 mmol), 2-nitro-4-(trifluoromethyl)aniline (206 mg, 1.0 mmol), Pd2dba3 (23 mg, 0.025 mmol), PCy2dmab (30 mg, 0.075 mmol), and Cs2CO3 (489 mg) are added to a round bottom flask. The flask is evacuated and filled with nitrogen two times and then left under vacuum for 5 min. After filling with nitrogen, toluene (4 mL Sureseal, degassed with nitrogen for 20 min) is added via syringe and the resultant dark red/black solution is heated to 100° C. with an oil bath. After 18 hr, the solution is cooled to room temperature and excess ethyl acetate is added. After washing with 1M HCl two times, the organic layer is washed with brine, dried over MgSO4, filtered through Celite, and concentrated to give crude material. This solid was purified by flash chromatography to afford 4-{[2-nitro-4-(trifluoromethyl)phenyl]amino}benzonitrile. The yield is 288 mg (94%).

Provenance & Evidence