Cesium carbonate → HCID 68814738, compound

HRID 732433Notes

Reaction equation

HRID 732433 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+].[CH:69]1([NH2:73])[CH2:72][CH2:71][CH2:70]1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]([C:5]1[CH:10]=[C:9]([NH:73][CH:69]2[CH2:72][CH2:71][CH2:70]2)[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 75645CyclobutylamineHCID 634876Binap, (A+-)-HCID 86615001HCID 86615001, compound

Product 1

HCID 68814738HCID 68814738, compoundYield 39.1%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

Add 6-chloropyridine-2,4-dicarboxylic acid 2-ethyl ester 4-methyl ester (0.500 g, 2.05 mmol), palladium acetate (0.0461 g, 0.205 mmol), racemic 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (0.128 g, 0.205 mmol), cesium carbonate (0.801 g, 2.46 mmol) and toluene (5 mL), to a sealed vessel flushed with nitrogen. Slowly add cyclobutylamine (0.210 mL, 2.46 mmol) and heat and stir the sealed vessel at 90° C. overnight. Cool to room temperature, filter through a pad of filtering agent, concentrate and purify (silica gel chromatography, eluting with 10:90 to 20:80 ethyl acetate:hexanes) to give the title compound (0.223 g, 39%).

Workup

  1. customto a sealed vessel flushed with nitrogen
  2. temperatureCool to room temperature
  3. filtrationfilter through a pad
  4. filtrationof filtering agent
  5. concentrationconcentrate
  6. custompurify
  7. wash(silica gel chromatography, eluting with 10:90 to 20:80 ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-39cbd7c87c0a422d84ce0321e2f5013e
Source dataset
uspto-grants-2009_09
Patent number
US07585885B2

Reaction notes

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