Water → HCID 87426391, compound

HRID 715383Notes

Reaction equation

HRID 715383 reaction equation
Cl[C:2]1[N:14]=[C:13]([O:15][CH2:16][CH:17]([F:19])[F:18])[CH:12]=[CH:11][C:3]=1[C:4]([O:6][CH2:7]C(F)F)=[O:5].[CH3:20][O-:21].[Na+].O>C1COCC1>[F:18][CH:17]([F:19])[CH2:16][O:15][C:13]1[CH:12]=[CH:11][C:3]([C:4]([O:6][CH3:7])=[O:5])=[C:2]([O:21][CH3:20])[N:14]=1

Participants

5

Reactant 3

HCID 962WaterHCID 10942334Sodium MethoxideHCID 87426370HCID 87426370, compound

Product 1

HCID 87426391HCID 87426391, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 2,2-difluoroethyl 2-chloro-6-(2,2-difluoroethoxy)nicotinate (2.9 g, 9.8 mmol, Step-1) in THF (35 mL) is added sodium methoxide (1.58 g, 29.2 mmol) at 0° C. Then the mixture is stirred at rt for 15 hours. The mixture is poured into water and extracted with DCM (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/EtOAc (4:1 to 1:4) to give 615 mg (26% yield) of the title compound as white solid.

Workup

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

Sources & evidence

ORD record
ord-709f5cf7be064240a17d9b0acd2140b6
Source dataset
uspto-grants-2015_11
Patent number
US09187475B2

Reaction notes

Loading…