Cesium carbonate → HCID 68814982, compound

HRID 732430Notes

Reaction equation

HRID 732430 reaction equation
[CH3:1][O:2][C:3](=[O:17])[C:4]1[CH:9]=[C:8]([S:10](=[O:15])(=[O:14])[N:11]([CH3:13])[CH3:12])[N:7]=[C:6](Cl)[CH:5]=1.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:70]([NH2:74])([CH2:72][CH3:73])[CH3:71]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1>[CH3:1][O:2][C:3](=[O:17])[C:4]1[CH:9]=[C:8]([S:10](=[O:15])(=[O:14])[N:11]([CH3:13])[CH3:12])[N:7]=[C:6]([NH:74][C@H:70]([CH2:72][CH3:73])[CH3:71])[CH:5]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 67137532-Butanamine, (S)-HCID 86615007HCID 86615007, compound

Product 1

HCID 68814982HCID 68814982, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

Add toluene (20 mL), 2-chloro-6-dimethylsulfamoyl-isonicotinic acid methyl ester (2.49 g, 8.93 mmol), palladium acetate (0.201 g, 0.893 mmol), racemic 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (0.556 g, 0.893 mmol) and cesium carbonate (4.36 g, 13.4 mmol) to a sealed vessel flushed with nitrogen. Slowly add (S)-sec-butylamine (1.36 mL, 13.4 mmol) to the mixture. 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 20:80 to 30:70 ethyl acetate:hexanes) to give the title compound (1.43 g, 51%).

Workup

  1. customflushed with nitrogen
  2. temperatureHeat
  3. temperatureCool to room temperature
  4. filtrationfilter through a pad
  5. filtrationof filtering agent
  6. concentrationconcentrate
  7. custompurify
  8. wash(silica gel chromatography, eluting with 20:80 to 30:70 ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-9f94c37a12ae4ba2aad201c31abf6a0f
Source dataset
uspto-grants-2009_09
Patent number
US07585885B2

Reaction notes

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