Cesium carbonate → HCID 68817414, compound

HRID 1436554Notes

Reaction equation

HRID 1436554 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[C:9](Cl)[N:8]=[C:7]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:6]=1)=[O:4].C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+].[C@@H:69]([NH2:73])([CH2:71][CH3:72])[CH3:70]>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:1][O:2][C:3]([C:5]1[CH:10]=[C:9]([NH:73][C@H:69]([CH2:71][CH3:72])[CH3:70])[N:8]=[C:7]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:6]=1)=[O:4]

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 67137532-Butanamine, (S)-HCID 86615001HCID 86615001, compound

Product 1

HCID 68817414HCID 68817414, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

Add 6-chloropyridine-2,4-dicarboxylic acid 2-ethyl ester 4-methyl ester (2.44 g, 10 mmol), palladium acetate (224 mg, 1.0 mmol), racemic-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (623 mg, 1.0 mmol), cesium carbonate (4.95 g, 15.2 mmol) in toluene (70 mL) in a sealed tube. Degas the tube for 5 min with nitrogen, add (S)-sec-butylamine (1.2 mL, 11.8 mmol) and seal the tube. Heat to 80° C. overnight. Cool to room temperature and filter the mixture through a filtering agent. Wash with ethyl acetate. Dissolve the solid in water and extract with ethyl acetate. Combine all organic solutions, concentrate and purify (silica gel chromatography, eluting with ethyl acetate and hexanes) to give the title compound (2.5 g, 90%).

Workup

  1. customDegas the tube for 5 min with nitrogen
  2. customseal the tube
  3. temperatureCool to room temperature
  4. filtrationfilter the mixture through a filtering agent
  5. washWash with ethyl acetate
  6. dissolutionDissolve the solid in water
  7. extractionextract with ethyl acetate
  8. concentrationCombine all organic solutions, concentrate
  9. custompurify
  10. wash(silica gel chromatography, eluting with ethyl acetate and hexanes)

Sources & evidence

ORD record
ord-e757c9781beb4e169984d37a7df28c59
Source dataset
uspto-grants-2009_11
Patent number
US07618978B2

Reaction notes

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