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

HRID 1959757
Notes
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Reaction equation

HRID 1959757 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 69810525(5,7-Difluoroquinolin-6-yl)methanol

Product 1

HCID 698103402-(5,7-Difluoroquinolin-6-ylmethyl)isoindoline-1,3-dioneYield 81%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent
2×

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

  1. temperatureAfter cooling
  2. customevaporating
  3. customthe residue was purified by silica gel with hexane

Sources & evidence

ORD record
ord-051fd454639d470a8dfbc3c731653a1b
Source dataset
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08410264B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes