Cesium carbonate → HCID 86760757, compound

HRID 271562Notes

Reaction equation

HRID 271562 reaction equation
CC(C)(C)C[N:4]1[C:8]2[N:9]=[C:10]([C:13]#[N:14])[N:11]=[CH:12][C:7]=2[CH:6]=[C:5]1[CH2:15][N:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1.Br[C:25]1[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][C:26]=1[F:32].[C:33]1([C:48]2[CH:53]=CC=C[CH:49]=2)C=CC=CC=1P(C(C)(C)C)C(C)(C)C.[C:54](=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CCOC(C)=O.CCCCCC.O>[CH3:33][C:48]([CH3:53])([CH3:54])[CH2:49][C:12]1[C:7]2[CH:6]=[C:5]([CH2:15][N:16]3[CH2:17][CH2:18][N:19]([C:25]4[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][C:26]=4[F:32])[CH2:20][CH2:21]3)[NH:4][C:8]=2[N:9]=[C:10]([C:13]#[N:14])[N:11]=1

Participants

10

Reactant 4

HCID 10796Cesium carbonateHCID 5732804-Bromo-3-fluorotolueneHCID 27342152-(Di-tert-butylphosphino)biphenylHCID 59834726HCID 59834726, compound

Product 1

HCID 86760757HCID 86760757, compoundYield 18%

Reagents, catalysts & solvents 5

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A suspension of 7-(2,2-dimethyl-propyl)-6-piperazin-1-ylmethyl-7H-pyrrolo[2,3-d]pyrimidine-2-carbonitrile (0.32 mmol), 4-bromo-3-fluorotoluene (3.84 mmol), biphenyl-2-yl-di-tert-butyl-phosphane (0.064 mmol), palladium acetate (0.064 mmol), cesium carbonate (0.45 mmol) in 1,4-dioxane is stirred at 100° C. for 24 h and poured into water. The mixture is extracted with AcOEt. The organic layer is washed with water, dried over magnesium sulfate, and concentrated. Purification by silica gel column chromatography gives the product in 18% yield. R-0.56 (n-hexane:AcOEt=1:1)

Workup

  1. extractionThe mixture is extracted with AcOEt
  2. washThe organic layer is washed with water
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customPurification by silica gel column chromatography
  6. customgives the product in 18% yield

Sources & evidence

ORD record
ord-279abb38d3e444279a6c45f271ad670b
Source dataset
uspto-grants-2008_11
Patent number
US07452886B2

Reaction notes

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