Cesium carbonate → HCID 86655164, compound

HRID 1877451Notes

Reaction equation

HRID 1877451 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][C:60]([O:63][C:64](=[O:85])[NH:65][C:66]1[CH:71]=[CH:70][C:69]([C:72]2[C:84]3[C:83]4[C:78](=[CH:79][CH:80]=[CH:81][CH:82]=4)[NH:77][C:76]=3[CH:75]=[CH:74][CH:73]=2)=[CH:68][N:67]=1)([CH3:62])[CH3:61]>O1CCOCC1.C(OC(C)C)(C)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:6]([C:5]1[CH:8]=[CH:9][C:2]([N:77]2[C:76]3[CH:75]=[CH:74][CH:73]=[C:72]([C:69]4[CH:70]=[CH:71][C:66]([NH:65][C:64](=[O:85])[O:63][C:60]([CH3:61])([CH3:59])[CH3:62])=[N:67][CH:68]=4)[C:84]=3[C:83]3[C:78]2=[CH:79][CH:80]=[CH:81][CH:82]=3)=[CH:3][C:4]=1[F:10])#[N:7]

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 7360294-Bromo-2-fluorobenzonitrileHCID 86655163HCID 86655163, compound

Product 1

HCID 86655164HCID 86655164, compoundYield 31.8%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 7914Diisopropyl EtherSolventHCID 312751,4-DioxaneSolvent

Procedure

0.217 g of 4-bromo-2-fluorobenzonitrile, 0.9 g of caesium carbonate, 0.05 g of (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphane) and 0.016 g of palladium acetate are successively added, under argon, to a solution of 0.26 g of 2-methylpropan-2-yl[5-(9H-carbazol-4-yl)pyridin-2-yl]carbamate in 15 ml of dioxane. The reaction mixture is refluxed for 5 hours, cooled to ambient temperature and filtered through celite. The filtrate is concentrated under reduced pressure so as to give a brown oil which, after trituration in diisopropyl ether, gives a yellow solid which is purified by silica gel chromatography, elution being carried out with a mixture of cyclohexane and ethyl acetate (90/10 by volume). 0.11 g of 2-methylpropan-2-yl {5-[9-(4-cyano-3-fluorophenyl)-9H-carbazol-4-yl]pyridin-2-yl}carbamate is thus obtained, the characteristics of which are the following:

Workup

  1. temperatureThe reaction mixture is refluxed for 5 hours
  2. filtrationfiltered through celite
  3. concentrationThe filtrate is concentrated under reduced pressure so as
  4. customto give a brown oil which
  5. customis purified by silica gel chromatography, elution
  6. additionbeing carried out with a mixture of cyclohexane and ethyl acetate (90/10 by volume)

Sources & evidence

ORD record
ord-26e4b03d2a924279995a2bfe8c3953f4
Source dataset
uspto-grants-2012_11
Patent number
US08309721B2

Reaction notes

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