Benzophenone imine → N-(Diphenylmethylene)-5-fluoroquinolin-7-amine

Participants

Reaction Conditions

Reaction Steps

A mixture of 7-bromo-5-fluoroquinoline (128 mg, 0.566 mmol), benzophenone imine (0.143 mL, 0.849 mmol, Aldrich), Pd(dba)2 (32.6 mg, 0.057 mmol, Strem), 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (70.5 mg, 0.113 mmol, Aldrich) and sodium 2-methylpropan-2-olate (82 mg, 0.849 mmol, Aldrich) in toluene (4 mL) was stirred at 110° C. for 5 h. The mixture was cooled down to room temperature. The reaction mixture was diluted with saturated NH4Cl (10 mL) and extracted with EtOAc (2×40 mL). The combined organic extracts were washed with saturated NaCl (10 mL) and dried over Na2SO4. The solution was filtered and concentrated in vacuo to give the crude material as a light-yellow solid, which was used for the next step without purification.

Provenance & Evidence