Sodium methanolate methanol → Methyl 2-bromo-5-methoxyisonicotinate

HRID 1468291Notes

Reaction equation

HRID 1468291 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:10](F)=[CH:11][N:12]=1)[C:5]([O:7][CH2:8]C)=[O:6].[CH3:14][O-:15].[Na+].CO>CO>[Br:1][C:2]1[CH:3]=[C:4]([C:10]([O:15][CH3:14])=[CH:11][N:12]=1)[C:5]([O:7][CH3:8])=[O:6]

Participants

4

Reactant 2

HCID 23694274Sodium methanolate methanolHCID 46311464Ethyl 2-bromo-5-fluoroisonicotinate

Product 1

HCID 86710106Methyl 2-bromo-5-methoxyisonicotinateYield 36%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Ethyl 2-bromo-5-fluoroisonicotinate (434 mg, 1.75 mmol) obtained in step 1 was dissolved in methanol (3.50 mL), and the solution was stirred at room temperature for 30 minutes after adding a 28% sodium methoxide-methanol solution (1.69 g, 8.75 mmol). The reaction mixture was extracted with ethyl acetate after adding water. The organic layer was washed with water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give methyl 2-bromo-5-methoxyisonicotinate (154 mg, yield 36%).

Workup

  1. extractionThe reaction mixture was extracted with ethyl acetate
  2. additionafter adding water
  3. washThe organic layer was washed with water and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-5f033193a1124361a2e8e0e7830b94b8
Source dataset
uspto-grants-2015_04
Patent number
US09000186B2

Reaction notes

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