Phthalimide → 2-(5,7-Difluoroquinolin-6-ylmethyl)isoindoline-1,3-dione

HRID 1892424Notes

Reaction equation

N(/C(OC(C)C)=O)=N\C(OC(C)C)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[F:34][C:35]1[C:44]([CH2:45]O)=[C:43]([F:47])[CH:42]=[C:41]2[C:36]=1[CH:37]=[CH:38][CH:39]=[N:40]2.[C:48]1(=[O:58])[C:56]2[C:51](=[CH:52][CH:53]=[CH:54][CH:55]=2)[C:50](=[O:57])[NH:49]1>C1COCC1>[F:34][C:35]1[C:44]([CH2:45][N:49]2[C:50](=[O:57])[C:51]3[C:56](=[CH:55][CH:54]=[CH:53][CH:52]=3)[C:48]2=[O:58])=[C:43]([F:47])[CH:42]=[C:41]2[C:36]=1[CH:37]=[CH:38][CH:39]=[N:40]2

Participants

Conditions

Temperature: 40 °C

Procedure

A mixture of (E)-diisopropyl diazene-1,2-dicarboxylate (4.72 g, 23.36 mmol) and triphenylphosphine (6.13 g, 23.36 mmol) in THF (100 mL) was stirred for 15 min, and a solution of (5,7-difluoroquinolin-6-yl)methanol (3.80 g, 19.47 mmol) and isoindoline-1,3-dione (3.15 g, 21.42 mmol) in THF (200 mL) was added dropwise. The reaction mixture was heated at 40° C. for 24 h. After cooling and evaporating, the residue was purified by silica gel with hexane:EtOAc to provide 2-(5,7-difluoroquinolin-6-ylmethyl)isoindoline-1,3-dione (5.10 g, 81%). 1H-NMR (400 MHz, CDCl3) δ ppm 8.93 (m, 1H), 8.39 (m, 1H), 7.85 (m, 2H), 7.72 (m, 2H), 7.59 (d, 1H), 7.43 (m, 1H), 5.15 (s, 2H).

Workup

temperatureAfter cooling
customevaporating
customthe residue was purified by silica gel with hexane

Sources & evidence

ORD record: ord-47d0ef24eff34bab92bd8250a958a934
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08507676B2

Reaction notes

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