Cesium carbonate → HCID 68815114, compound

HRID 732403Notes

Reaction equation

HRID 732403 reaction equation
[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[C:8](Cl)[N:7]=[C:6]([C:11](=[O:13])[CH3:12])[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:67]([NH2:71])([CH2:69][CH3:70])[CH3:68]>C1(C)C=CC=CC=1.C(OCC)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[C:8]([NH:71][C@H:67]([CH2:69][CH3:70])[CH3:68])[N:7]=[C:6]([C:11](=[O:13])[CH3:12])[CH:5]=1

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 67137532-Butanamine, (S)-HCID 72213903HCID 72213903, compound

Product 1

HCID 68815114HCID 68815114, compoundYield 17%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Procedure

Dissolve 2-acetyl-6-chloro-isonicotinic acid methyl ester (300 mg, 1.4 mmol), palladium (II) acetate (16 mg, 0.07 mmol), racemic 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (46 mg, 0.07 mmol) and cesium carbonate (781 mg, 2.1 mmol) in anhydrous toluene (3 mL) in a previously degassed sealed vessel. Flush the mixture with nitrogen gas. Add (S)-(+)-sec-butylamine (0.16 mL, 1.68 mmol) to the solution under nitrogen and heat the sealed mixture overnight at 100° C. Cool the reaction to room temperature. Dilute with diethyl ether and filter through a filtering agent. Concentrate the filtrate and purify (silica gel chromatography, eluting with 0:100 to 5:95 ethyl acetate:hexanes) to give the title compound as a solid (17%).

Workup

  1. customa previously degassed
  2. customsealed vessel
  3. customFlush the mixture with nitrogen gas
  4. temperatureCool
  5. customthe reaction to room temperature
  6. filtrationfilter through a filtering agent
  7. concentrationConcentrate the filtrate
  8. custompurify
  9. wash(silica gel chromatography, eluting with 0:100 to 5:95 ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-fc1f583a430a4dee9be5ad22748c922c
Source dataset
uspto-grants-2009_09
Patent number
US07585885B2

Reaction notes

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