Potassium Carbonate → HCID 22712065, compound

HRID 352549Notes

Reaction equation

HRID 352549 reaction equation
[Cl:1][C:2]1[C:3](F)=[N:4][C:5]([F:19])=[C:6]([Cl:18])[C:7]=1[O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([Br:17])[CH:10]=1.Cl.[CH3:22][O:23][C:24](=[O:27])[CH2:25][NH2:26].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.[Cl-].[Na+].O>[Cl:18][C:6]1[C:5]([F:19])=[N:4][C:3]([NH:26][CH2:25][C:24]([O:23][CH3:22])=[O:27])=[C:2]([Cl:1])[C:7]=1[O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([Br:17])[CH:10]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 122755Glycine methyl ester hydrochlorideHCID 22712081HCID 22712081, compound

Product 1

HCID 22712065HCID 22712065, compoundYield 85.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of 3,5-dichloro-2,6-difluoro-4-(3-bromo-4-methoxyphenoxy)pyridine (250 mg) and glycine methyl ester hydrochloric acid (150 mg) in DMF (2.0 mL) was added potassium carbonate powder (250 mg) in one portion. The resulting mixture was stirred at ambient temperature for 20 hours. The reaction mixture was diluted with brine and extracted with ethyl acetate (50 mL×2). The combined organic layers were washed with brine (50 mL×3), dried (Na2SO4) and concentrated. Chromatography with ethyl acetate-hexanes (0-50% gradient elution) provided the title compound as a white solid (253 mg).

Workup

  1. extractionextracted with ethyl acetate (50 mL×2)
  2. washThe combined organic layers were washed with brine (50 mL×3)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-0d19b07878134f07868875fa2109a741
Source dataset
uspto-grants-2004_06
Patent number
US06747048B2

Reaction notes

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