Potassium Phosphate, Tribasic → HCID 89690469, 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 (400.0 mg, 0.80 mmol, 100 mol %), 1M aqueous potassium phosphate, tribasic (1.6 ml, 1.60 mmol, 200 mol %), tricyclohexylphosphine (22.4 mg, 0.08 mmol, 10 mol %), tributyl-vinyl-stannane (304.4 mg, 0.96 mmol, 120 mol %) and palladium(II) acetate (9.0 mg, 0.04 mmol, 5 mol %) were dissolved in 12.0 mL of dioxane in a 40 mL scintillation vial and the vessel was sealed and heated to 100° C. for 16 h. The reaction was then diluted with water and ethyl acetate and filtered through a pad of Celite. The filtrate was extracted twice with ethyl acetate and the combined organics were dried over sodium sulfate and concentrated. After two column chromatography runs, first with dichloromethane/methanol and then with ethyl acetate/methanol, 5-nitro-N-[3-(2-oxo-pyrrolidin-1-yl)-propyl]-4-(4-o-tolyl-piperazin-1-yl)-2-vinyl-benzamide 6a (41.0 mg, 0.08 mmol, 10.4%) was obtained in pure form. LCMS (ESI) 492 (M+H).

Provenance & Evidence