Water → HCID 15479547, compound

Participants

Reaction Steps

A 25 mL round bottom flask was connected to a reflux condenser and the apparatus flame-dried under high vacuum. The vacuum was broken by the addition of dry argon, and the flask was allowed to cool to room temperature. The flask was charged with 0.295 g (0.90 mmol) of powdered anhydrous cesium carbonate, 12 mg (0.013 mmol) of tris(dibenzylideneacetone)dipalladium(0) (Pd2 (dba)3), and 12 mg (0.019 mmol) of (S)-(-)-2,2'-bis(diphenylphosphino)1,1'-binaphthyl (BINAP), and the apparatus was evacuated and filled with dry argon 3 times. A solution of (1-isopropyl-4,4-dimethyl-2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)amine (Compound 1, 0.18 g, 775 mmol) and ethyl 4-iodoobenzoate (0.178 g, 0.65 mmol, available as described in U.S. Pat. No. 5,616,712) in 2 mL of dry toluene was added and the flask was immersed in an oil bath heated to 100° C. After 16 hours, 6 mg of Pd2 (dba)3 and 6 mg of BINAP were added and stirring at 100° C. was continued until the reaction was complete as judged by TLC analysis. The solution was cooled to room temperature and poured into a separatory funnel containing water and ether. The layers were separated and the aqueous layer was extracted 3 times with ether. The combined ether layers were washed once with brine, and dried over magnesium sulfate, and the solvents were removed under reduced pressure. The residue was purified by flash chromatography on silica gel using 10% ethyl acetate in hexanes, and gave the title compound.

Provenance & Evidence