Cesium carbonate → HCID 57580808, compound

HRID 552392Notes

Reaction equation

HRID 552392 reaction equation
C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.[Cl:47][C:48]1[N:53]2[CH:54]=[CH:55][N:56]=[C:52]2[C:51](I)=[CH:50][CH:49]=1.C([O-])([O-])=O.[Cs+].[Cs+].[CH:64]([N:67]1[CH2:72][CH2:71][N:70]([C:73]2[CH:78]=[CH:77][C:76]([NH2:79])=[CH:75][CH:74]=2)[CH2:69][CH2:68]1)([CH3:66])[CH3:65]>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:47][C:48]1[N:53]2[CH:54]=[CH:55][N:56]=[C:52]2[C:51]([NH:79][C:76]2[CH:75]=[CH:74][C:73]([N:70]3[CH2:69][CH2:68][N:67]([CH:64]([CH3:66])[CH3:65])[CH2:72][CH2:71]3)=[CH:78][CH:77]=2)=[CH:50][CH:49]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 91615454-[4-(Propan-2-yl)piperazin-1-yl]anilineHCID 534859535-Chloro-8-iodoimidazo[1,2-a]pyridine

Product 1

HCID 57580808HCID 57580808, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Procedure

Palladium acetate (4.67 mg, 0.021 mmol) and rac-BINAP (12.95 mg, 0.021 mmol) are sonicated in toluene (4.5 mL) under nitrogen, at room temperature for 5 minutes in a microwave tube. 5-Chloro-8-iodo-imidazo[1,2-a]pyridine (116 mg, 0.417 mmol), Cs2CO3 (679.7 mg, 2.09 mmol) and 4-(4-isopropyl-piperazin-1-yl)-phenylamine (109.59 mg, 0.502 mmol) are then added at room temperature. The reaction mixture is then allowed to proceed at reflux for 16 hours at which point no starting material is visible by LC-MS. After concentration, the mixture is diluted in dichloromethane, and washed with 10% aqueous citric acid solution. The aqueous phase is then basified to pH 7 with saturated aqueous NaHCO3, and extracted with dichloromethane. The combined organic layers are dried (MgSO4) and the solvent is removed under reduced pressure to yield title compound, which is used as such for the next step.

Workup

  1. temperatureat reflux for 16 hours at which point no starting material
  2. concentrationAfter concentration
  3. additionthe mixture is diluted in dichloromethane
  4. washwashed with 10% aqueous citric acid solution
  5. extractionextracted with dichloromethane
  6. dry with materialThe combined organic layers are dried (MgSO4)
  7. customthe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-d8884fece3ff4d128c2807f7749e819e
Source dataset
uspto-grants-2011_05
Patent number
US07951818B2

Reaction notes

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