Water → HCID 67508524, compound

HRID 623486Notes

Reaction equation

HRID 623486 reaction equation
Cl[C:2]1[N:11]=[C:10]([O:12][CH2:13][C:14]([F:17])([F:16])[F:15])[C:9]([F:18])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[CH3:19][O-:20].[Na+].O>C1COCC1>[F:18][C:9]1[C:10]([O:12][CH2:13][C:14]([F:17])([F:16])[F:15])=[N:11][C:2]([O:20][CH3:19])=[C:3]([CH:8]=1)[C:4]([O:6][CH3:7])=[O:5]

Participants

5

Reactant 3

HCID 962WaterHCID 10942334Sodium MethoxideHCID 87426645HCID 87426645, compound

Product 1

HCID 67508524HCID 67508524, compoundYield 28.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of methyl 2-chloro-5-fluoro-6-(2,2,2-trifluoroethoxy)nicotinate (1.1 g, 3.9 mmol, Step-1 of Amine-42) in THF (35 mL) is added sodium methanolate (0.32 g, 5.8 mmol) at 0° C. The mixture is stirred at 60° C. for 2 hours and cooled to room temperature. The mixture is poured into water and extracted with dichloromethane (10 mL×3). The combined organic layer is washed with water, brine, and dried over sodium sulfate. The organic solvent is removed under reduced pressure. The residue is purified by column chromatography on silica gel eluting with n-hexane/ethyl acetate (9:1) to give 310 mg (28% yield) of the title compound as a white solid.

Workup

  1. temperaturecooled to room temperature
  2. extractionextracted with dichloromethane (10 mL×3)
  3. washThe combined organic layer is washed with water, brine
  4. dry with materialdried over sodium sulfate
  5. customThe organic solvent is removed under reduced pressure
  6. customThe residue is purified by column chromatography on silica gel eluting with n-hexane/ethyl acetate (9:1)

Sources & evidence

ORD record
ord-a8623c2907d5452c8ac011c53d831ca9
Source dataset
uspto-grants-2016_04
Patent number
US09302991B2

Reaction notes

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