[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:15]=[C:16]3[C:20](=[CH:21][CH:22]=2)[N:19](S(C2C=CC=CC=2)(=O)=O)[CH:18]=[C:17]3[C:32]#[N:33])[CH:10]([CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([O-])([O-])=O.[K+].[K+]>CO.O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:15]=[C:16]3[C:20](=[CH:21][CH:22]=2)[NH:19][CH:18]=[C:17]3[C:32]#[N:33])[CH:10]([CH2:34][C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]To a suspension of 4-(1-benzenesulfonyl-3-cyano-1H-indol-5-yl)-3-benzyl-piperazine-1-carboxylic acid tert-butyl ester (0.37 g, 0.7 mmol) in 10 mL MeOH was added K2CO3 (0.27 g, 2.0 mmol) in 2 mL H2O. The reaction mixture was stirred for 30 minutes and then solution was concentrated under reduced pressure and extracted with EtOAc. The combine organic layers were dried over MgSO4, filtered, and concentrated under reduced pressure. Purification via flash chromatography (25% EtOAc in hexane) afforded 3-benzyl-4-(3-cyano-1H-indol-5-yl)-piperazine-1-carboxylic acid tert-butyl ester (0.23 g, 85%) as a white foam; MS (M+H)=417.
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