Phthalimide → 2-((5-Bromopyridin-3-yl)methyl)isoindoline-1,3-dione
Reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:8]O)[CH:5]=[N:6][CH:7]=1.[C:10]1(=[O:20])[NH:14][C:13](=[O:15])[C:12]2=[CH:16][CH:17]=[CH:18][CH:19]=[C:11]12.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][N:14]2[C:10](=[O:20])[C:11]3[C:12](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:13]2=[O:15])[CH:5]=[N:6][CH:7]=1Participants
Procedure
To a stirred solution of (5-bromopyridin-3-yl)methanol (LII) (1.60 g, 8.5 mmol, 1 eq), phthalimide (1.24 g, 8.5 mmol, 1 eq) and PPh3 (3.33 g, 12.75 mmol, 1.5 eq) in anhydrous THF (15 mL) was added DEAD (2.21 g, 12.75 mmol, 1.5 eq) dropwise at 0° C. under N2. Then the reaction mixture was stirred at room temperature for 6 h. The mixture was washed with saturated NaHCO3 solution (15 mL), water (15 mL) and brine (15 mL) subsequently. The organic layers were dried over MgSO4, concentrated under reduced pressure, the resultant residue was purified by flash chromatography on silica gel (PE:EtOAc=4:1) to give 2-((5-bromopyridin-3-yl)methyl)isoindoline-1,3-dione (LIII) (2.5 g, 7.88 mmol, 82.3% yield) as a white solid. ESIMS found for C14H9BrN2O2 m/z 317 (M+H).
Workup
- washThe mixture was washed with saturated NaHCO3 solution (15 mL), water (15 mL) and brine (15 mL) subsequently
- dry with materialThe organic layers were dried over MgSO4
- concentrationconcentrated under reduced pressure
- customthe resultant residue was purified by flash chromatography on silica gel (PE:EtOAc=4:1)
Sources & evidence
- ORD record
- ord-e5f740392dc5407c8f0821c3c38dff77
- Source dataset
- uspto-grants-2014_03
- Patent number
- US08664241B2
Reaction notes
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