Cesium carbonate → HCID 25051861, compound

HRID 570833Notes

Reaction equation

HRID 570833 reaction equation
[C:1]1([C:7]2[C:8]([C:12]#[N:13])=[CH:9][NH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[I-].C(=O)([O-])[O-].[Cs+].[Cs+].[Cl:21][C:22]1[CH:27]=[C:26](I)[CH:25]=[CH:24][N:23]=1>CS(C)=O.ClCCl.O>[Cl:21][C:22]1[CH:27]=[C:26]([N:10]2[CH:11]=[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[C:8]([C:12]#[N:13])=[CH:9]2)[CH:25]=[CH:24][N:23]=1

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 30165Iodide IonHCID 15165112-Chloro-4-iodopyridineHCID 37214604-Phenyl-1H-pyrrole-3-carbonitrile

Product 1

HCID 25051861HCID 25051861, compoundYield 57.3%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-phenyl-1H-pyrrole-3-carbonitrile (0.168 g), cupper (I) iodide (0.019 g), N,N-dimethyl grycine (0.021 g) and cesium carbonate (0.325 g) in dimethylsulfoxide (10 mL) was added 2-chloro-4-iodopyridine (0.287 g) at room temperature, and this mixture was at 180° C. in a sealed tube under microwave irradiation for 5 minutes. After cooling to ambient temperature, this reaction mixture was diluted with dichloromethane and water, and the insoluble material was removed by filtered though a Celite pad. This organic layer was separated and this organic solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: ethyl acetate/hexane=80/20) to give the title compound (0.16 g).

Workup

  1. customthis mixture was at 180° C. in a sealed tube under microwave irradiation for 5 minutes
  2. customthe insoluble material was removed
  3. filtrationby filtered though a Celite pad
  4. customThis organic layer was separated
  5. customthis organic solvent was removed under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel (eluent: ethyl acetate/hexane=80/20)

Sources & evidence

ORD record
ord-73369f0f47fe421b88c834729a70470f
Source dataset
uspto-grants-2015_05
Patent number
US09023882B2

Reaction notes

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