Cesium carbonate → HCID 68816946, compound

HRID 732459Notes

Reaction equation

HRID 732459 reaction equation
[CH:1]1([NH2:5])[CH2:4][CH2:3][CH2:2]1.[CH3:6][O:7][C:8](=[O:20])[C:9]1[CH:14]=[C:13]([S:15]([CH3:18])(=[O:17])=[O:16])[N:12]=[C:11](Cl)[CH:10]=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+]>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:6][O:7][C:8](=[O:20])[C:9]1[CH:14]=[C:13]([S:15]([CH3:18])(=[O:17])=[O:16])[N:12]=[C:11]([NH:5][CH:1]2[CH2:4][CH2:3][CH2:2]2)[CH:10]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 75645CyclobutylamineHCID 634876Binap, (A+-)-HCID 86615009HCID 86615009, compound

Product 1

HCID 68816946HCID 68816946, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

Add cyclobutylamine (0.13 mL, 1.5 mmol) to a suspension of 2-chloro-6-methanesulfonyl-isonicotinic acid methyl ester (0.25 g, 1.0 mmol), palladium acetate (0.022 g, 0.1 mmol), racemic 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (0.062 g, 0.1 mmol), and cesium carbonate (0.325 g, 1.0 mmol) in toluene (5 mL) at room temperature and heat for 16 h at 80° C. Cool, filter through a filtering agent, concentrate and purify (silica gel chromatography, eluting with 15:85 to 40:60 ethyl acetate:hexanes) to give the title compound (0.255 g, 90%).

Workup

  1. temperatureCool
  2. filtrationfilter through a filtering agent
  3. concentrationconcentrate
  4. custompurify
  5. wash(silica gel chromatography, eluting with 15:85 to 40:60 ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-97afbe16c5114be6a69653e17db7e6d3
Source dataset
uspto-grants-2009_09
Patent number
US07585885B2

Reaction notes

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