C[O:2][C:3](=[O:29])[CH2:4][CH:5]1[C:13]2[C:8](=[CH:9][C:10]([Cl:14])=[CH:11][CH:12]=2)[N:7](C(OCC)=O)[CH:6]1[C:20]([C:22]1[CH:27]=[C:26]([CH3:28])[CH:25]=[CH:24][N:23]=1)=[O:21].Cl>C(O)C.[OH-].[Na+]>[Cl:14][C:10]1[CH:9]=[C:8]2[C:13]([C:5]([CH2:4][C:3]([OH:29])=[O:2])=[C:6]([C:20]([C:22]3[CH:27]=[C:26]([CH3:28])[CH:25]=[CH:24][N:23]=3)=[O:21])[NH:7]2)=[CH:12][CH:11]=1A stirred solution of methyl[6-chloro-1-ethoxycarbonyl-2-(4-methylpyridine-2-carbonyl)indolin-3-yl]acetate (step 2, 930 mg, 2.2 mmol) in ethanol (20 ml) and 2N aqueous NaOH (10 ml) was heated at reflux temperature for 72 h. After cooling to room temperature, the resulting mixture was neutralized with 2N aqueous HCl (10 ml) and concentrated. The residue was diluted in dichloromethane/mehanol (10:1, 300 ml) and dried (MgSO4). After removal of solvent, the crude product was purified by flash column chromatography eluting with dichloromethane/methanol (20:1) and then washed with i-PrOH (ca.20 ml) to give 120 mg (17%) of the title compound as a yellow powder.
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