Cesium carbonate → HCID 66732690, compound

HRID 1966843Notes

Reaction equation

HRID 1966843 reaction equation
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+].Br[C:54]1[CH:59]=[CH:58][N:57]=[CH:56][CH:55]=1.[CH2:60]([N:62]1[C:66]2[N:67]=[CH:68][C:69]([C:72]3[CH2:79][C:75]4([CH2:78][CH2:77][CH2:76]4)[O:74][N:73]=3)=[C:70]([NH2:71])[C:65]=2[CH:64]=[N:63]1)[CH3:61]>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:60]([N:62]1[C:66]2[N:67]=[CH:68][C:69]([C:72]3[CH2:79][C:75]4([CH2:76][CH2:77][CH2:78]4)[O:74][N:73]=3)=[C:70]([NH:71][C:54]3[CH:59]=[CH:58][N:57]=[CH:56][CH:55]=3)[C:65]=2[CH:64]=[N:63]1)[CH3:61]

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 142684-BromopyridineHCID 634876Binap, (A+-)-HCID 66732901HCID 66732901, compound

Product 1

HCID 66732690HCID 66732690, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 312751,4-DioxaneSolvent

Procedure

2,2′-Bis(diphenylphosphino)-1,1′-binaphthyl (0.3 equivalent), palladium acetate (0.09 equivalent) and cesium carbonate (1.5 equivalent) is added to 4-bromo pyridine (1 equivalent) in anhydrous dioxane under inert atmosphere. 1-Ethyl-5-(5-oxa-6-azaspiro[3.4]oct-6-en-7-yl)-1H-pyrazolo[3,4-b]pyridin-4-amine (1.3 equivalent) (example 36) is added and the reaction mixture is stirred at reflux for about 10-12 hours. It is cooled to room temperature and filtered through celite. The reaction mixture is extracted with ethyl acetate. The organic layer is washed with water, dried over anhydrous sodium sulphate and concentrated in vacuo. The crude compound is purified by column chromatography.

Workup

  1. temperatureat reflux for about 10-12 hours
  2. filtrationfiltered through celite
  3. extractionThe reaction mixture is extracted with ethyl acetate
  4. washThe organic layer is washed with water
  5. dry with materialdried over anhydrous sodium sulphate
  6. concentrationconcentrated in vacuo
  7. customThe crude compound is purified by column chromatography

Sources & evidence

ORD record
ord-0264ae035df84c6c87c05642a23b4e4e
Source dataset
uspto-grants-2013_04
Patent number
US08420666B2

Reaction notes

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