Cesium carbonate → HCID 66576564, compound

HRID 523538Notes

Reaction equation

HRID 523538 reaction equation
CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.C(=O)([O-])[O-].[Cs+].[Cs+].[CH:49]1([C:52]2[CH:57]=[CH:56][N:55]=[CH:54][C:53]=2[N:58]2[CH2:62][CH2:61][NH:60][C:59]2=[O:63])[CH2:51][CH2:50]1.Cl[C:65]1[N:70]=[C:69]([C:71]([F:74])([F:73])[F:72])[CH:68]=[CH:67][N:66]=1>C1(C)C=CC=CC=1.C(Cl)(Cl)Cl.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].CO>[CH:49]1([C:52]2[CH:57]=[CH:56][N:55]=[CH:54][C:53]=2[N:58]2[CH2:62][CH2:61][N:60]([C:65]3[N:70]=[C:69]([C:71]([F:74])([F:73])[F:72])[CH:68]=[CH:67][N:66]=3)[C:59]2=[O:63])[CH2:51][CH2:50]1

Participants

9

Reactant 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 27739122-Chloro-4-(trifluoromethyl)pyrimidineHCID 709820071-(4-Cyclopropylpyridin-3-yl)imidazolidin-2-one

Product 1

HCID 66576564HCID 66576564, compoundYield 35%

Reagents, catalysts & solvents 4

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 887MethanolSolventHCID 1140TolueneSolventHCID 6212ChloroformSolvent

Conditions

Temperature
110 °C

Procedure

Xantphos (23 mg, 0.049 mmol) and Pd2(dba)3 (22.5 mg, 0.024 mmol) were added to a solution of cesium carbonate (400 mg, 1.23 mmol) in toluene (5 mL) previously purged with nitrogen (20 minutes). The reaction mixture was purged with argon for 10 minutes, followed by the addition of, 1-(4-cyclopropylpyridin-3-yl)imidazolidin-2-one (I-1d: 100 mg, 0.492 mmol) and 2-chloro-4-(trifluoromethyl)pyrimidine (0.06 ml, 0.54 mmol). The reaction mixture was heated in seal tube at 110° C. for 16 hours. The reaction was monitored by TLC (10% methanol in chloroform). The reaction mixture was cooled, filtered and the filtrate partitioned between ethyl acetate and water. The organic layer was concentrated to yield the crude product. Purification by column chromatography on silica gel (1.5% methanol in chloroform) afforded 60 mg of the product (35% yield).

Workup

  1. custompreviously purged with nitrogen (20 minutes)
  2. customThe reaction mixture was purged with argon for 10 minutes
  3. temperatureThe reaction mixture was cooled
  4. filtrationfiltered
  5. customthe filtrate partitioned between ethyl acetate and water
  6. concentrationThe organic layer was concentrated
  7. customto yield the crude product
  8. customPurification by column chromatography on silica gel (1.5% methanol in chloroform)

Sources & evidence

ORD record
ord-4ee147569a64468fb7f2d5e4ae1ff484
Source dataset
uspto-grants-2016_05
Patent number
US09339501B2

Reaction notes

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