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

HRID 965880Notes

Reaction equation

HRID 965880 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-0f45ee14e89e4498b1ce2195065c6215
Source dataset
uspto-grants-2005_10
Patent number
US06951875B2

Reaction notes

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