Phthalimide → 2-((5-Bromopyridin-3-yl)methyl)isoindoline-1,3-dione

HRID 1350108Notes

Reaction equation

HRID 1350108 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:20]1(=[O:30])[NH:24][C:23](=[O:25])[C:22]2=[CH:26][CH:27]=[CH:28][CH:29]=[C:21]12.[Br:31][C:32]1[CH:33]=[N:34][CH:35]=[C:36]([CH2:38]O)[CH:37]=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[Br:31][C:32]1[CH:37]=[C:36]([CH2:38][N:24]2[C:20](=[O:30])[C:21]3=[CH:29][CH:28]=[CH:27][CH:26]=[C:22]3[C:23]2=[O:25])[CH:35]=[N:34][CH:33]=1

Participants

6

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 2784733(5-Bromo-3-pyridinyl)methanol

Product 1

HCID 229922612-((5-Bromopyridin-3-yl)methyl)isoindoline-1,3-dioneYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

5-Bromo-3-(phthalimidomethyl)pyridine is produced by adding triphenylphosphine (12.1 g, 46.3 mmol) and phthalimide (6.80 g, 46.3 mmol) in dry THF (70 mL) to a stirred suspension of 3-bromo-5-hydroxymethylpyridine (6.70 g, 35.6 mmol), and then adding a solution of diethyl azodicarboxylate (7.30 mL, 46.3 mmol) in dry THF (30 mL) drop-wise. The reaction mixture was stirred at room temperature overnight. After removal of the solvent by rotary evaporation, the crude material was purified by column chromatography to yield 5-bromo-3-(phthalimidomethyl)pyridine (9.5 g, 85% yield).

Workup

  1. customAfter removal of the solvent
  2. customby rotary evaporation
  3. customthe crude material was purified by column chromatography

Sources & evidence

ORD record
ord-d534a5edbd804aed8e6589546674cfa0
Source dataset
uspto-grants-2007_05
Patent number
US07214686B2

Reaction notes

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