Potassium Phosphate, Tribasic → HCID 89690465, compound

Participants

Reaction Conditions

Reaction Steps

2-Chloro-5-nitro-N-[3-(2-oxo-pyrrolidin-1-yl)-propyl]-4-(4-o-tolyl-piperazin-1-yl)-benzamide 1f (200.0 mg, 0.40 mmol, 100 mol %), potassium phosphate tribasic (169.8 mg, 0.80 mmol, 200 mol %), cyclopropylboronic acid (41.2 mg, 0.48 mmol, 120 mol %), tricyclohexylphosphine (11.2 mg, 0.04 mmol, 10 mol %), and palladium(II) acetate (4.5 mg, 0.02 mmol, 5 mol %) were combined in de-gassed toluene (4.0 ml) and 200 mL of water was added. The vessel was sealed and heated to 100° C. for 3 h and then the reaction was cooled and diluted with water and ethyl acetate. The suspension was filtered through a pad of Celite and the mixture was extracted twice with ethyl acetate and the combined organic extracts were dried over sodium sulfate and concentrated. Column chromatography (dichloromethane to 10% methanol in dichloromethane) afforded 2-cyclopropyl-5-nitro-N-[3-(2-oxo-pyrrolidin-1-yl)-propyl]-4-(4-o-tolyl-piperazin-1-yl)-benzamide 5a (161.0 mg; 0.32 mmol; 79.6%) as an amorphous yellow solid. LCMS (ESI) 506 (M+H).

Provenance & Evidence