[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[CH2:3][C:2]1=[O:10].[Li+].C[Si]([N-][Si](C)(C)C)(C)C.C1COCC1.O1CCCCC1[O:32][CH2:33][CH2:34][CH2:35][C:36]1[CH:37]=[C:38]2[C:42](=[CH:43][CH:44]=1)[C:41](=O)[O:40][CH2:39]2.OS(O)(=O)=O.[OH-].[Na+]>O1CCCC1>[OH:32][CH2:33][CH2:34][CH2:35][C:36]1[CH:37]=[C:38]2[C:42](=[CH:43][CH:44]=1)[C:41](=[C:3]1[C:4]3[C:5](=[N:6][CH:7]=[CH:8][CH:9]=3)[NH:1][C:2]1=[O:10])[O:40][CH2:39]2To a stirred solution of 1,3-dihydro-pyrrolo[2,3-b]pyridin-2-one (193 mg (1.44 mmol) in anhydrous tetrahydrofuran (10 ml) under N2 was added 1.0M LiHMDS/THF solution (2.9 ml, 2.9 mmol). The mixture was stirred at room temperature for 10 minutes, then 5-[3-(tetrahydro-pyran-2-yloxy)-propyl]-3H-isobenzofuran-1-one (200 mg, 0.72 mmol) was added. The mixture was stirred at room temperature for 2.5 hours and poured into 1M H2SO4 solution (20 ml). The mixture was heated at 55° C. for 15 minutes, cooled to room temperature and poured into an ice water (200 ml). The mixture was basified to pH 9 with NaOH solution and stirred overnight. The solid was filtered, washed with water and dried under vacuum to give 3-[5-(3-hydroxy-propyl)-3H-isobenzofuran-1-ylidene]-1,3-dihydro-pyrrolo[2,3-b]pyridin-2-one as a brown solid (20 mg, 9%).
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