methyl N-[(3S)-pyrrolidin-3-yl]carbamate;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 (0.16 g, 0.23 mmol, from Example 47, Step 2), methyl (3S)-pyrrolidin-3-ylcarbamate hydrochloride (0.035 g, 0.19 mmol), palladium acetate (0.87 mg, 0.0039 mmol), (S)-(−)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (3.6 mg, 0.0058 mmol), and cesium carbonate (0.24 g, 0.74 mmol) in tetrahydrofuran (4 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 and evaporated. The residue was purified on silica gel (eluting with 0 to 5% MeOH in dichloromethane) to give the desired product (47 mg, 70%). LCMS calculated for C17H19ClN3O3 (M+H)+: m/z=348.1; Found: 348.4. The mixture was cooled filtered The filtrate was washed with brine dried over MgSO4 evaporated The residue was purified on silica gel (eluting with 0 to 5% MeOH in dichloromethane)