Cesium carbonate → HCID 68815841, compound

HRID 732420Notes

Reaction equation

HRID 732420 reaction equation
[CH3:1][O:2][C:3](=[O:17])[C:4]1[CH:9]=[C:8]([S:10]([CH:13]([CH3:15])[CH3:14])(=[O:12])=[O:11])[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]([CH:13]([CH3:15])[CH3:14])(=[O:12])=[O:11])[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 86615003HCID 86615003, compound

Product 1

HCID 68815841HCID 68815841, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

Add 2-chloro-6-isopropanesulfonyl-isonicotinic acid methyl ester (1.26 g, 4.53 mmol), toluene (20 mL), palladium acetate (102 mg, 0.453 mmol), racemic 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (282 mg, 0.453 mmol) and cesium carbonate (2.21 g, 6.80 mmol) to a sealed vessel flushed with nitrogen. Slowly add (S)-sec-butylamine (0.68 mL, 6.80 mmol) to the mixture. Heat and stir the sealed vessel at 90° C. overnight. Cool to room temperature, concentrate and purify (silica gel chromatography, eluting with 20:80 to 70:30 ethyl acetate:hexanes) to give the title compound.

Workup

  1. customflushed with nitrogen
  2. temperatureHeat
  3. temperatureCool to room temperature
  4. concentrationconcentrate
  5. custompurify
  6. wash(silica gel chromatography, eluting with 20:80 to 70:30 ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-a4d3cff2b2354668be536dc9a531ad27
Source dataset
uspto-grants-2009_09
Patent number
US07585885B2

Reaction notes

Loading…