[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8]O)=[N:6][CH:7]=1.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:47]1(=[O:57])[NH:51][C:50](=[O:52])[C:49]2=[CH:53][CH:54]=[CH:55][CH:56]=[C:48]12>C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][N:51]2[C:47](=[O:57])[C:48]3[C:49](=[CH:53][CH:54]=[CH:55][CH:56]=3)[C:50]2=[O:52])=[N:6][CH:7]=1A mixture of (5-bromopyridin-2-yl)methanol (1.2 g, 6.38 mmol), 1,1′-(azodicarbonyl)-dipiperidine (2.093 g, 8.30 mmol), triphenylphosphine (2.176 g, 8.30 mmol) and phthalimide (1.221 g, 8.30 mmol) in THF (60 mL) at rt was stirred over the weekend. The reaction mixture was filtered and the filtrate was concentrated to a yellow solid that was triturated with methanol. Filtration and drying afforded 2-((5-bromopyridin-2-yl)methyl)isoindoline-1,3-dione (1.295 g, 4.08 mmol, 64.0% yield) as a colorless crystalline solid. 1H NMR (400 MHz, DMSO-d6) δ 8.57 (d, J=2.0 Hz, 1H), 8.03 (dd, J=8.4, 2.2 Hz, 1H), 7.90 (d, J=9.0 Hz, 4H), 7.44 (d, J=8.4 Hz, 1H), 4.89 (s, 2H). MS (ES+) m/z: 316.95, 318.96 (M+H); LC retention time: 2.297 min (analytical HPLC Method O).
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