Cesium carbonate → HCID 68814422, compound

HRID 732450Notes

Reaction equation

HRID 732450 reaction equation
[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][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:64]([NH2:68])([CH2:66][CH3:67])[CH3:65]>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][N:7]=[C:6]([NH:68][C@H:64]([CH2:66][CH3:67])[CH3:65])[CH:5]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 2736842Methyl 2-chloropyridine-4-carboxylateHCID 67137532-Butanamine, (S)-

Product 1

HCID 68814422HCID 68814422, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

Degas with nitrogen a suspension containing 2-chloro-isonicotinic acid methyl ester (2.15 g, 12.5 mmol), palladium acetate (281 mg, 1.25 mmol), racemic 2,2′-bis(diphenylphosphino)-1,1′-binapthyl (780 mg, 1.25 mmol), cesium carbonate (4.95 g, 15 mmol), and (S)-sec-butylamine (1.5 mL, 15 mmol) in toluene (30 mL) and heat in a sealed tube at 90° C. overnight. Cool to room temperature and filter the solids through a filtering agent. Wash with ethyl acetate (30 mL), concentrate and purify (silica gel chromatography, eluting with 15:85 to 30:70 ethyl acetate:hexanes) to give the title compound.

Workup

  1. customDegas with nitrogen a suspension
  2. temperatureCool to room temperature
  3. filtrationfilter the solids through a filtering agent
  4. washWash with ethyl acetate (30 mL)
  5. concentrationconcentrate
  6. custompurify
  7. wash(silica gel chromatography, eluting with 15:85 to 30:70 ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-c02367ab068e480294bcdf90d46230a8
Source dataset
uspto-grants-2009_09
Patent number
US07585885B2

Reaction notes

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