Water → HCID 117818878, compound

HRID 1753211Notes

Reaction equation

HRID 1753211 reaction equation
Cl[C:2]1[N:11]=[C:10]([CH3:12])[C:9]([F:13])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[CH3:14][O-:15].[Na+].O>C1COCC1>[F:13][C:9]1[C:10]([CH3:12])=[N:11][C:2]([O:15][CH3:14])=[C:3]([CH:8]=1)[C:4]([O:6][CH3:7])=[O:5]

Participants

5

Reactant 3

HCID 962WaterHCID 10942334Sodium MethoxideHCID 57516327HCID 57516327, compound

Product 1

HCID 117818878HCID 117818878, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of methyl 2-chloro-5-fluoro-6-methylnicotinate (18) (0.8 g, 3.92 mmol,) in THF (35 mL) was added sodium methanolate (0.42 g, 7.85 mmol) at 0° C. The mixture was stirred at 60° C. for 6 hours and cooled to room temperature. Then the mixture was poured into water and extracted with dichloromethane (2×50 mL). The combined organic layer was washed with water, brine and solvent was evaporated under reduced pressure. The residue was purified by column chromatography on silica gel eluting with 10% ethyl acetate in hexane to give methyl 5-fluoro-2-methoxy-6-methylnicotinate (19) (250 mg, 32%) as a white solid.

Workup

  1. temperaturecooled to room temperature
  2. extractionextracted with dichloromethane (2×50 mL)
  3. washThe combined organic layer was washed with water, brine and solvent
  4. customwas evaporated under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel eluting with 10% ethyl acetate in hexane

Sources & evidence

ORD record
ord-3a9487798948431e86ece8ec5955ff82
Source dataset
uspto-grants-2015_10
Patent number
US09163020B2

Reaction notes

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