[H-].[Na+].[OH:3][C@@H:4]1[CH2:8][CH2:7][N:6]([C:9]([C:11]2[S:19][C:18]3[C:13](=[N:14][CH:15]=[CH:16][C:17]=3[Cl:20])[CH:12]=2)=[O:10])[CH2:5]1.[CH3:21]I.[C-]#N.[K+]>C1COCC1>[Cl:20][C:17]1[CH:16]=[CH:15][N:14]=[C:13]2[CH:12]=[C:11]([C:9]([N:6]3[CH2:7][CH2:8][C@@H:4]([O:3][CH3:21])[CH2:5]3)=[O:10])[S:19][C:18]=12NaH (2.1 g, 53.1 mmol) was added to a solution of (3R)-(3-hydroxy-pyrrolidin-1-yl)-[7-chloro-thieno[3,2-b]pyridin-2-yl]-methanone (5.0 g, 17.7 mmol) in THF (100 mL), at 0° C. The reaction mixture was allowed to stir for 20 min., and MeI (3.26 g, 22.9 mmol) was added dropwise. After 3 h the reaction was treated with saturated aqueous KCN. The aqueous layer was extracted with CH2Cl2. The combined organic layers were dried (Na2SO4), and the solvent was removed under reduced pressure. Purification by flash chromatography on silica gel, eluting with CH2Cl2/MeOH (94:6) afforded the title compound as a white solid (3.2 g, 61%). MS: 297.2/299.2 (MH+); HPLC Rf: 4.25 min.; HPLC purity: 95%.
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