N(C(OC(C)C)=O)=NC(OC(C)C)=O.[Br:15][C:16]1[CH:17]=[C:18]2[C:22](=[CH:23][CH:24]=1)[C:21](=[O:25])[N:20]([C@@H:26]([CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[C:32]([C:36]#[C:37][Si:38]([CH3:41])([CH3:40])[CH3:39])[CH:31]=1)[CH2:27]O)[CH2:19]2.[C:42]1(=[O:52])[NH:46][C:45](=[O:47])[C:44]2=[CH:48][CH:49]=[CH:50][CH:51]=[C:43]12.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[Br:15][C:16]1[CH:17]=[C:18]2[C:22](=[CH:23][CH:24]=1)[C:21](=[O:25])[N:20]([C@@H:26]([CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[C:32]([C:36]#[C:37][Si:38]([CH3:41])([CH3:40])[CH3:39])[CH:31]=1)[CH2:27][N:46]1[C:42](=[O:52])[C:43]3[C:44](=[CH:48][CH:49]=[CH:50][CH:51]=3)[C:45]1=[O:47])[CH2:19]2To a solution of diisopropyl azodicarboxylate (0.35 mL, 1.8 mmol) in tetrahydrofuran (2.9 mL) was added 5-bromo-2-((1S)-2-hydroxy-1-{3-[(trimethylsilyl)ethynyl]benzyl}ethyl)-isoindolin-1-one (0.58 g, 1.3 mmol), phthalimide (0.21 g, 1.4 mmol), and triphenylphosphine (0.35 g, 1.3 mmol). The mixture was stirred at room temperature for 4 h. Direct purification by combi-flash chromatography eluting with 0-60% EtOAc in hexanes afforded the desired product. LC-MS found: 571.1 (M+H)+.
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