methyl N-piperidin-4-ylcarbamate;hydrochloride

Conditions: temp:65.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A stirred mixture of 7-acetyl-5-chloroquinolin-8-yl trifluoromethanesulfonate (0.12 g, 0.17 mmol, from Example 47, Step 2), methyl piperidin-4-ylcarbamate hydrochloride (0.028 g, 0.14 mmol), palladium acetate (0.64 mg, 0.0029 mmol), (S)-(−)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (2.7 mg, 0.0043 mmol), and cesium carbonate (0.18 g, 0.55 mmol) in tetrahydrofuran (3 mL) was heated at 65° C. overnight. The mixture was cooled, diluted with dichloromethane and filtered. The filtrate was washed with brine, dried over MgSO4, evaporated and then purified on silica gel (eluting with 0 to 5% methanol in dichloromethane) to give the desired product (21 mg, 40%). LCMS calculated for C18H21ClN3O3 (M+H)+: m/z=362.1; Found: 362.1. The mixture was cooled filtered The filtrate was washed with brine dried over MgSO4 evaporated purified on silica gel (eluting with 0 to 5% methanol in dichloromethane)