Water → HCID 59355376, compound

HRID 887704Notes

Reaction equation

HRID 887704 reaction equation
[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[C:8]([Cl:10])[N:7]=[C:6](Br)[C:5]=1[NH2:12].[C:14](=O)([O-])[O-].[K+].[K+].CB1OB(C)OB(C)O1.O>O1CCOCC1>[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[C:8]([Cl:10])[N:7]=[C:6]([CH3:14])[C:5]=1[NH2:12]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 574072TrimethylboroxineHCID 59355453Methyl 3-amino-2-bromo-6-chloro-4-pyridinecarboxylate

Product 1

HCID 59355376HCID 59355376, compoundYield 26.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

3-Amino-2-bromo-6-chloroisonicotinic acid methyl ester (500 mg), potassium carbonate (829 mg), tetrakis(triphenyl phosphine)palladium(0) and trimethylboroxine (276 mg) were suspended in dioxane (15 mL). Water (1.5 mL) was added and the mixture was degassed using subsequent evaporation and flushing with nitrogen (5×). The reaction mixture was stirred under reflux for 7 hours. After cooling to room temperature, the mixture was quenched with water and extracted 2× with ethyl acetate. The combined organic layer was washed with brine, dried over MgSO4 and concentrated in vacuum. The residue was purified by column chromatography (silica 60, hexane/ethyl acetate=3:1, Rf=0.25) to afford 100 mg of the title compound of the formula

Workup

  1. customthe mixture was degassed
  2. customevaporation
  3. customflushing with nitrogen (5×)
  4. temperatureunder reflux for 7 hours
  5. customthe mixture was quenched with water
  6. extractionextracted 2× with ethyl acetate
  7. washThe combined organic layer was washed with brine
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated in vacuum
  10. customThe residue was purified by column chromatography (silica 60, hexane/ethyl acetate=3:1, Rf=0.25)

Sources & evidence

ORD record
ord-fdd725c27c344041857b94a3b8c3062d
Source dataset
uspto-grants-2012_08
Patent number
US08247431B2

Reaction notes

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