[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[N:7]([C:13]1[CH:14]=[N:15][CH:16]=[C:17]([CH2:19][OH:20])[CH:18]=1)[CH2:6][CH2:5]2.[H-].[Na+].[H][H].[CH3:25]I>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[N:7]([C:13]1[CH:14]=[N:15][CH:16]=[C:17]([CH2:19][O:20][CH3:25])[CH:18]=1)[CH2:6][CH2:5]2
To a solution of 6-chloro-2-(5-hydroxymethyl-pyridin-3-yl)-3,4-dihydro-2H-isoquinolin-1-one (example 3) (28.8 mg, 0.1 mmol) in THF (5 mL) was added NaH (8 mg, 0.2 mmol, 60% dispersion in mineral oil) at room temperature. After hydrogen evolution ceased, a solution of methyliodide (0.2 mmol) in THF (5 mL) was added dropwise, and the resulting mixture was stirred at room temperature for 1 hour. The mixture was then treated with satd. aqueous NH4Cl solution and extracted three times with EtOAc. The combined organic layer was washed with water and brine, dried over anhy. Na2SO4 and concentrated in vacuo. The crude product was purified by prep-HPLC to give the title compound (4.5 mg, 14.8%) as a white solid. MS: (M+H)+ 303.1
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