Cesium carbonate → HCID 68817414, compound

HRID 732406Notes

Reaction equation

HRID 732406 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[C:9](Cl)[N:8]=[C:7]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:6]=1)=[O:4].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:69]([NH2:73])([CH2:71][CH3:72])[CH3:70]>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]([C:5]1[CH:10]=[C:9]([NH:73][C@H:69]([CH2:71][CH3:72])[CH3:70])[N:8]=[C:7]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:6]=1)=[O:4]

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 67137532-Butanamine, (S)-HCID 86615001HCID 86615001, compound

Product 1

HCID 68817414HCID 68817414, compoundYield 72%

Reagents, catalysts & solvents 3

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

Procedure

Dissolve 6-chloropyridine-2,4-dicarboxylic acid 2-ethyl ester 4-methyl ester (2.8 g, 11.5 mmol), palladium (II) acetate (258.0 mg, 1.15 mmol), racemic 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (716 mg, 1.15 mmol) and cesium carbonate (5.6 g, 17.2 mmol) in toluene (25 mL) in a previously degassed sealed vessel. Flush the mixture with nitrogen gas. Add (S)-(+)-sec-butylamine (1.38 mL, 13.8 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 10:90 ethyl acetate:hexanes) to give the title compound as an oil (72%).

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 10:90 ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-9d74536746294731a2cece8c27ec611a
Source dataset
uspto-grants-2009_09
Patent number
US07585885B2

Reaction notes

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