Potassium Carbonate → 2-Bromo-3-[oxiranylmethoxy]pyridine

HRID 431064Notes

Reaction equation

HRID 431064 reaction equation
[Br:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[CH:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+].S(C1C=CC(C)=CC=1)(O[CH2:19][C@H:20]1[O:22][CH2:21]1)(=O)=O>CN(C)C=O>[Br:1][C:2]1[C:7]([O:8][CH2:19][CH:20]2[CH2:21][O:22]2)=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 230702-Bromo-3-pyridinolHCID 153296Oxiranemethanol, 4-methylbenzenesulfonate, (S)-

Product 1

HCID 222566772-Bromo-3-[oxiranylmethoxy]pyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
57.5 °C

Procedure

To a mixture of 25.2 g (0.145 mole) of 2-bromo-3-pyridinol and 30 g (0.22 mole) of potassium carbonate in 80 mL of N,N-dimethylformamide was added 30 g (0.13 mole) of (S)-glycidyl tosylate. The mixture was heated under nitrogen at 55-60° C. for 15 hours. The solvent was then removed in vacuum and replaced with 500 mL of methylene chloride, and the solution was washed with 500 mL of water and with saturated brine, dried over sodium sulfate, filtered and concentrated in vacuum. The residue was column chromatographed on silica gel with methylene chloride as eluant to give 17 g of the (S)-enantiomer of the title compound as a white solid. 1H-NMR (CDCl3): multiplet 8.01 δ (1 H); multiplet 7.22 δ (2 H); doublet of doublets 4.38 δ (1 H); multiplet 4.04 δ (1 H); multiplet 3.40 δ (1 H); multiplet 2.95 δ (1 H); multiplet 2.85 δ (1 H).

Workup

  1. customThe solvent was then removed in vacuum
  2. washthe solution was washed with 500 mL of water and with saturated brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuum
  6. customchromatographed on silica gel with methylene chloride as eluant

Sources & evidence

ORD record
ord-e06dd6afbbdc4b13810c5471425dc310
Source dataset
uspto-grants-2003_12
Patent number
US06656950B2

Reaction notes

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