Sodium Methoxide → HCID 89964266, compound

HRID 1846236Notes

Reaction equation

HRID 1846236 reaction equation
[Br:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[C:4](Cl)[N:3]=1.[CH3:10][O-:11].[Na+]>CN(C=O)C>[Br:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[C:4]([O:11][CH3:10])[N:3]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 467386822-Bromo-6-chloropyridin-3-ol

Product 1

HCID 89964266HCID 89964266, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a 0° C. solution of 2-bromo-6-chloropyridin-3-ol (1 eq.) and DMF (0.2 M) is added NaOMe (2.2 eq.). The solution is allowed to warm to room temperature as the cooling bath expires and allowed to stir at room temperature for 24 h. The reaction is quenched with saturated NH4Cl and diluted with water. The aqueous solution is extracted with EtOAc. The combined EtOAc layers are dried over MgSO4, concentrated in vacuo, and purified by column chromatography to give the title compound.

Workup

  1. customThe reaction is quenched with saturated NH4Cl
  2. additiondiluted with water
  3. extractionThe aqueous solution is extracted with EtOAc
  4. dry with materialThe combined EtOAc layers are dried over MgSO4
  5. concentrationconcentrated in vacuo
  6. custompurified by column chromatography

Sources & evidence

ORD record
ord-da3795bddaca487fa6f4a27f388fbeab
Source dataset
uspto-grants-2015_02
Patent number
US08952009B2

Reaction notes

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