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Water → 2-(1-(2-(2-(Methylsulfonyl)phenyl)-1,5-naphthyridin-3-yl)ethyl)isoindoline-1,3-dione

HRID 473439
Notes
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Reaction equation

HRID 473439 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]1[C:20]([CH:21](O)[CH3:22])=[CH:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][N:17]=2)[N:12]=1)(=[O:4])=[O:3].[C:24]1(=[O:34])[NH:28][C:27](=[O:29])[C:26]2=[CH:30][CH:31]=[CH:32][CH:33]=[C:25]12.N(C(OC(C)C)=O)=NC(OC(C)C)=O.O>C1COCC1>[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]1[C:20]([CH:21]([N:28]2[C:24](=[O:34])[C:25]3[C:26](=[CH:30][CH:31]=[CH:32][CH:33]=3)[C:27]2=[O:29])[CH3:22])=[CH:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][N:17]=2)[N:12]=1)(=[O:3])=[O:4]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 6809PhthalimideHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 58318628HCID 58318628, compound

Product 1

HCID 583186362-(1-(2-(2-(Methylsulfonyl)phenyl)-1,5-naphthyridin-3-yl)ethyl)isoindoline-1,3-dione

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Procedure

To a mixture of crude of 1-(2-(2-(methylsulfonyl)phenyl)-1,5-naphthyridin-3-yl)ethanol (700 mg, 2.13 mmol) and phthalimide (627 mg, 4.26 mmol) in THF (21 mL) was added triphenylphosphene (1.12 g, 4.26 mmol) at 0° C. The reaction mixture was stirred for 10 min at same temperature. Diisopropyl azodicarboxylate (0.9 mL, 4.26 mmol) was added to mixture at 0° C. The reaction mixture was stirred for overnight at 0° C. Water was added to reaction mixture and extracted with EtOAc. The organic layer was dried over Na2SO4 and concentrated in vacuo to give 2-(1-(2-(2-(methylsulfonyl)phenyl)-1,5-naphthyridin-3-yl)ethyl)isoindoline-1,3-dione: LC-MS (ESI) m/z 458.1 [M+H]+. It was carried on crude for next step.

Workup

  1. additionwas added triphenylphosphene (1.12 g, 4.26 mmol) at 0° C
  2. stirringThe reaction mixture was stirred for overnight at 0° C
  3. extractionextracted with EtOAc
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8dd5528d39a948789fea9a04b00fa25d
Source dataset
uspto-grants-2014_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08633313B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes