C1(S([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([F:19])[CH:18]=[C:13]3[CH:12]=[C:11]2[C:20]([C:27]2[CH:32]=[CH:31][C:30]([C:33]([OH:36])([CH3:35])[CH3:34])=[CH:29][CH:28]=2)=[CH:21][CH:22]2[CH2:26][CH2:25][CH2:24][CH2:23]2)(=O)=O)C=CC=CC=1.[OH-].[Na+].N>C(O)C.O1CCCC1>[CH:22]1([CH:21]=[C:20]([C:27]2[CH:32]=[CH:31][C:30]([C:33]([OH:36])([CH3:34])[CH3:35])=[CH:29][CH:28]=2)[C:11]2[NH:10][C:14]3=[N:15][CH:16]=[C:17]([F:19])[CH:18]=[C:13]3[CH:12]=2)[CH2:26][CH2:25][CH2:24][CH2:23]1To a solution of 2-{4-[1-(1-benzenesulfonyl-5-fluoro-1H-pyrrolo[2,3-b]pyridin-2-yl)-2-cyclopentyl-vinyl]-phenyl}-propan-2-ol (220 mg, 0.43 mmol) in ethanol (20 mL) and tetrahydrofuran (10 mL) was added an aqueous sodium hydroxide solution (10%, 3.0 mL) and an aqueous saturated ammonia solution (1.5 mL). The mixture was refluxed for 12 h, cooled to room temperature, extracted with ethyl acetate, dried over anhydrous sodium sulfate and then concentrated in vacuo to afford 2-{4-[2-cyclopentyl-1-(5-fluoro-1H-pyrrolo[2,3-b]pyridin-2-yl)-vinyl]-phenyl}-propan-2-ol (150 mg, 94%) which was used in the next step without purification: LC/MS m/e calcd for C23H25FN2O [M+H]+ 365.47, observed 365.3.
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