Cesium carbonate → HCID 67308549, compound

HRID 1877440Notes

Reaction equation

HRID 1877440 reaction equation
Br[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([F:10])[CH: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.[CH3:59][O:60][C:61]([C:63]1[C:75]2[C:74]3[C:69](=[CH:70][CH:71]=[CH:72][CH:73]=3)[NH:68][C:67]=2[CH:66]=[CH:65][CH:64]=1)=[O:62]>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:59][O:60][C:61]([C:63]1[C:75]2[C:74]3[C:69](=[CH:70][CH:71]=[CH:72][CH:73]=3)[N:68]([C:2]3[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([F:10])[CH:3]=3)[C:67]=2[CH:66]=[CH:65][CH:64]=1)=[O:62]

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 7360294-Bromo-2-fluorobenzonitrileHCID 19897888Methyl 9H-carbazole-4-carboxylate

Product 1

HCID 67308549HCID 67308549, compoundYield 81.1%

Reagents, catalysts & solvents 2

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

Procedure

0.43 g of 4-bromo-2-fluorobenzonitrile, 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 added successively 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 3 hours, and then cooled, filtered and concentrated under reduced pressure. The residue is purified by silica gel chromatography, elution being carried out with a mixture of heptane and ethyl acetate (96/4 by volume), so to give 496 mg of 9-(4-cyano-3-fluorophenyl)-9H-carbazole-4-carboxylic acid methyl ester, the characteristics of which are the following:

Workup

  1. customobtained
  2. temperatureThe reaction mixture is refluxed for 3 hours
  3. temperaturecooled
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue is purified by silica gel chromatography, elution
  7. additionbeing carried out with a mixture of heptane and ethyl acetate (96/4 by volume)

Sources & evidence

ORD record
ord-194e233567554b6a9201bf5918cd8175
Source dataset
uspto-grants-2012_11
Patent number
US08309721B2

Reaction notes

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