Sodium Carbonate → HCID 55296760, compound

HRID 2281296Notes

Reaction equation

HRID 2281296 reaction equation
Br[CH2:2][CH:3]([C:5]1[N:10]=[CH:9][C:8]([C:11]#[N:12])=[C:7]([O:13][CH3:14])[CH:6]=1)[OH:4].C(=O)([O-])[O-].[Na+].[Na+]>CO>[CH3:14][O:13][C:7]1[CH:6]=[C:5]([CH:3]2[CH2:2][O:4]2)[N:10]=[CH:9][C:8]=1[C:11]#[N:12]

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 66643875HCID 66643875, compound

Product 1

HCID 55296760HCID 55296760, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 6-(2-bromo-1-hydroxyethyl)-4-methoxypyridine-3-carbonitrile (74.0 mg, 0.288 mmol) in anhydrous methanol (7 mL) was treated with sodium carbonate (61.0 mg, 0.576 mmol, 2.0 equiv), and allowed to stir at room temperature overnight. The solvent was evaporated. The residue was taken up in EtOAc (30 mL) and washed with water and brine. After drying over Na2SO4, the organic layer was removed and the residue was purified over SiO2 (10-45% EtOAc/hexanes as eluent) to yield 4-methoxy-6-(oxiran-2-yl)pyridine-3-carbonitrile.

Workup

  1. customThe solvent was evaporated
  2. washwashed with water and brine
  3. dry with materialAfter drying over Na2SO4
  4. customthe organic layer was removed
  5. customthe residue was purified over SiO2 (10-45% EtOAc/hexanes as eluent)

Sources & evidence

ORD record
ord-b88a767b1f9b4f48907b5dcac63e993a
Source dataset
uspto-grants-2015_09
Patent number
US09139585B2

Reaction notes

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