Cesium carbonate → HCID 22032003, compound

HRID 1792487Notes

Reaction equation

HRID 1792487 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:55]=[CH:56][C:57]([F:62])=[C:58]([CH:61]=1)[C:59]#[N:60].[N:63]1([C:69]([O:71][C:72]([CH3:75])([CH3:74])[CH3:73])=[O:70])[CH2:68][CH2:67][NH:66][CH2:65][CH2:64]1>C1(C)C=CC=CC=1.[Pd].[Pd].C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1>[C:59]([C:58]1[CH:61]=[C:54]([N:66]2[CH2:65][CH2:64][N:63]([C:69]([O:71][C:72]([CH3:75])([CH3:74])[CH3:73])=[O:70])[CH2:68][CH2:67]2)[CH:55]=[CH:56][C:57]=1[F:62])#[N:60]

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 143452tert-Butyl piperazine-1-carboxylateHCID 634876Binap, (A+-)-HCID 27249005-Bromo-2-fluorobenzonitrile

Product 1

HCID 22032003HCID 22032003, compound

Reagents, catalysts & solvents 2

HCID 9832798Tris(dibenzylideneacetone) dipalladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

1.24 g of 2,2′-bis (diphenylphosphino)-1,1′-binaphthyl and 229 mg of tris (dibenzylideneacetone) dipalladium were dissolved in toluene and stirred at 80° C. for 10 minutes. The reaction mixture was returned to room temperature, and 2.28 g cesium carbonate, 1.0 g 5-bromo-2-fluorobenzonitrile and 1.09 g t-butyl 1-piperazine carboxylate were added thereto and stirred at 80° C. for 12 hours. The reaction solution was purified by silica gel column chromatography to give the title compound.

Workup

  1. customwas returned to room temperature
  2. stirringstirred at 80° C. for 12 hours
  3. customThe reaction solution was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-a7dcc9b3fced469691d85657b923039b
Source dataset
uspto-grants-2006_07
Patent number
US07074801B1

Reaction notes

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