Phthalimide → 2-((6-Bromopyridin-2-yl)methyl)isoindoline-1,3-dione

HRID 1797110Notes

Reaction equation

HRID 1797110 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([CH2:8]O)[CH:5]=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:29]1(=[O:39])[NH:33][C:32](=[O:34])[C:31]2=[CH:35][CH:36]=[CH:37][CH:38]=[C:30]12.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[Br:1][C:2]1[N:7]=[C:6]([CH2:8][N:33]2[C:29](=[O:39])[C:30]3[C:31](=[CH:35][CH:36]=[CH:37][CH:38]=3)[C:32]2=[O:34])[CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 3517811(6-Bromopyridin-2-yl)methanolHCID 5462977Diethyl azodicarboxylate

Product 1

HCID 221764462-((6-Bromopyridin-2-yl)methyl)isoindoline-1,3-dioneYield 66%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of (6-bromo-pyridin-2-yl)-methanol (3.37 g, 17.9 mmol) (H. Tsukube et al., J. Org. Chem., 1993, 58, 4389), triphenylphosphine (5.17 g, 19.7 mmol) and phtalimide (2.90 g, 19.7 mmol) in THF was cooled in an ice bath. A solution of diethylazodicarboxylate (3.43 g, 19.7 mmol) in THF (15 ml) was added slowly and the mixture was left to reach rt. Stirring was continued for 17 hr, then the solvent was distilled off and the residue chromatographed (SiO2 with hexane/AcOEt=4/1) to provide 3.42 g (66%) of the title compound as a colorless viscous oil. MS: m/e=316 (M+H+).

Workup

  1. waitthe mixture was left
  2. customto reach rt
  3. distillationthe solvent was distilled off
  4. customthe residue chromatographed (SiO2 with hexane/AcOEt=4/1)

Sources & evidence

ORD record
ord-33ec9cdb62b0456ea0063b451ebce465
Source dataset
uspto-grants-2006_04
Patent number
US07034044B2

Reaction notes

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