N-[(3S)-pyrrolidin-3-yl]methanesulfonamide;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 (0.17 g, 0.25 mmol, from Example 47, Step 2), N-[(3S)-pyrrolidin-3-yl]methanesulfonamide hydrochloride (0.062 g, 0.31 mmol), palladium acetate (1.1 mg, 0.0049 mmol), (S)-(−)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (4.6 mg, 0.0074 mmol), and cesium carbonate (0.31 g, 0.94 mmol) in tetrahydrofuran (4 mL, 50 mmol) was heated at 65° C. overnight. The mixture was cooled, diluted with dichloromethane and filtered. The filtrate were washed with brine, dried over MgSO4, evaporated and purified on silica gel (eluting with 0 to 5% methanol in dichloromethane) to give the desired product (37 mg, 41%). LCMS calculated for C16H19ClN3O3S (M+H)+: m/z=368.1; Found: 368.1. The mixture was cooled filtered The filtrate were washed with brine dried over MgSO4 evaporated purified on silica gel (eluting with 0 to 5% methanol in dichloromethane)