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

HRID 1892433Notes

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]([CH:45](O)[CH3:46])=[C:43]([F:48])[CH:42]=[C:41]2[C:36]=1[CH:37]=[CH:38][CH:39]=[N:40]2.[C:49]1(=[O:59])[C:57]2[C:52](=[CH:53][CH:54]=[CH:55][CH:56]=2)[C:51](=[O:58])[NH:50]1>C1COCC1>[F:34][C:35]1[C:44]([CH:45]([N:50]2[C:51](=[O:58])[C:52]3[C:57](=[CH:56][CH:55]=[CH:54][CH:53]=3)[C:49]2=[O:59])[CH3:46])=[C:43]([F:48])[CH:42]=[C:41]2[C:36]=1[CH:37]=[CH:38][CH:39]=[N:40]2

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of (E)-diisopropyl diazene-1,2-dicarboxylate (3.8 g, 18.9 mmol) and triphenylphosphine (5.4 g, 20.5 mmol) in THF (50 mL) was stirred for 30 min, and a solution of 1-(5,7-difluoroquinolin-6-yl)ethanol (3.3 g, 15.8 mmol) and isoindoline-1,3-dione (2.7 g, 17.4 mmol) in THF (50 mL) was added dropwise. The reaction mixture was heated at 50° C. overnight. After cooling and evaporating, the residue was purified by silica gel and eluted with hexane/EtOAc to give the title compound as a white solid (2.6 g, 49%). LCMS (method A): [MH]+=339, tR=5.81 min.

Workup

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

Sources & evidence

ORD record: ord-c43f0f150a7b441b872f9d6ff4bcc1f7
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08507676B2

Reaction notes

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