Cesium carbonate → HCID 67307888, compound

HRID 1877448Notes

Reaction equation

HRID 1877448 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]#[N:9])=[CH:4][N:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C)C2C=CC=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=2OC2C1=CC=CC=2P(C1C=CC=CC=1)C1C=CC=CC=1.[CH3:58][O:59][C:60]([C:62]1[C:74]2[C:73]3[C:68](=[CH:69][CH:70]=[CH:71][CH:72]=3)[NH:67][C:66]=2[CH:65]=[CH:64][CH:63]=1)=[O:61]>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:58][O:59][C:60]([C:62]1[C:74]2[C:73]3[C:68](=[CH:69][CH:70]=[CH:71][CH:72]=3)[N:67]([C:2]3[CH:7]=[CH:6][C:5]([C:8]#[N:9])=[CH:4][N:3]=3)[C:66]=2[CH:65]=[CH:64][CH:63]=1)=[O:61]

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 50057186-Bromopyridine-3-carbonitrileHCID 19897888Methyl 9H-carbazole-4-carboxylate

Product 1

HCID 67307888HCID 67307888, compoundYield 64.7%

Reagents, catalysts & solvents 2

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

Procedure

0.49 g of 2-bromo-5-cyanopyridine, 2.2 g of caesium carbonate, 0.12 g of 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene and 0.04 g of palladium acetate are successively added to a solution of 0.40 g of 9H-carbazole-4-carboxylic acid methyl ester, obtained according to stage 2 of Example 1, in 30 ml of dioxane under an inert argon atmosphere. The reaction mixture is refluxed for 2 hours, and then cooled, filtered and concentrated under reduced pressure. The residue is purified by silica gel chromatography (15-40 μm), elution being carried out with a mixture of petroleum ether and dichloromethane (60/40 by volume), so as to give 376 mg of 9-(5-cyanopyridin-2-yl)-9H-carbazole-4-carboxylic acid methyl ester in the form of a yellow powder, the characteristics of which are the following:

Workup

  1. customobtained
  2. temperatureThe reaction mixture is refluxed for 2 hours
  3. temperaturecooled
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue is purified by silica gel chromatography (15-40 μm), elution
  7. additionbeing carried out with a mixture of petroleum ether and dichloromethane (60/40 by volume)

Sources & evidence

ORD record
ord-15f5ffc788784f21b2bb244ef3bdd187
Source dataset
uspto-grants-2012_11
Patent number
US08309721B2

Reaction notes

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