Cesium carbonate → HCID 68815041, compound

HRID 732401Notes

Reaction equation

HRID 732401 reaction equation
[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[C:8]([CH2:10][C:11]([F:14])([F:13])[CH3:12])[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: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](=[O:16])[C:4]1[CH:9]=[C:8]([CH2:10][C:11]([F:14])([F:13])[CH3:12])[N:7]=[C:6]([NH:73][C@H:69]([CH2:71][CH3:72])[CH3:70])[CH:5]=1

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 67137532-Butanamine, (S)-HCID 86081339HCID 86081339, compound

Product 1

HCID 68815041HCID 68815041, compoundYield 58%

Reagents, catalysts & solvents 3

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

Procedure

Dissolve 2-chloro-6-(2,2-difluoropropyl)-isonicotinic acid methyl ester-(150 mg, 0.6 mmol), palladium (II) acetate (224.0 mg, 1.0 mmol), racemic 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (37 mg, 0.06 mmol) and cesium carbonate (293 mg, 0.9 mmol) in toluene (2 mL) in a previously degassed sealed vessel. Flush the mixture with nitrogen gas. Add (S)-(+)-sec-butylamine (0.07 mL, 0.72 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 an oil (58%).

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-568aedb58c3e46f893ce47256603c114
Source dataset
uspto-grants-2009_09
Patent number
US07585885B2

Reaction notes

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