[NH:1]1[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C:2]1=[O:10].[Li+].C[Si]([N-][Si](C)(C)C)(C)C.C1COCC1.[C:26]1([C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH2:29][O:28]1)=O.Cl.C([O-])(O)=O.[Na+]>CN(C)C=O.O>[C:26]1(=[C:3]2[C:4]3=[N:5][CH:6]=[CH:7][CH:8]=[C:9]3[NH:1][C:2]2=[O:10])[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH2:29][O:28]1To a solution of 1,3-dihydro-pyrrolo[3,2-b]pyridin-2-one(50 mg, 0.37 mmol) in anhydrous N,N-dimethylformamide(5.0 ml) was added 1.0M LiHMDS/THF solution (0.74 ml, 0.74 mmol) under N2. After the mixture was stirred at room temperature for 10 minutes, phthalide was added (40 mg, 0.30 mmol), and then it was continuously stirred at room temperature for 4 hours. The mixture was poured into 2M HCl (4.0 ml), heated at 50° C. for 20 minutes and then poured into water (100 ml). After cooled to room temperature, the mixture was basified to pH 9 with saturated NaHCO3 solution, and was stirred at room temperature overnight. The resulting solid was filtered, washed with water, dried under vacuum and triturated with chloroform to give 3-(3H-isobenzofuran-1-ylidene)-1,3-dihydro-pyrrolo[3,2-b]pyridin-2-one as a yellow solid (12 mg, 16%).
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