Potassium Carbonate → HCID 86618172, compound

HRID 2094233Notes

Reaction equation

HRID 2094233 reaction equation
CB1OB(C)OB(C)O1.[CH3:10]C1(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-].[K+].[K+].[C:58]([C:60]1[C:64]([S:65][C:66]([F:69])([F:68])[F:67])=[C:63]([CH3:70])[N:62]([C:71]2[C:76](Cl)=[CH:75][C:74]([C:78]([F:81])([F:80])[F:79])=[CH:73][C:72]=2[Cl:82])[N:61]=1)#[N:59]>O1CCOCC1.C(OCC)(=O)C.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]>[Cl:82][C:72]1[CH:73]=[C:74]([C:78]([F:80])([F:81])[F:79])[CH:75]=[C:76]([CH3:10])[C:71]=1[N:62]1[C:63]([CH3:70])=[C:64]([S:65][C:66]([F:67])([F:68])[F:69])[C:60]([C:58]#[N:59])=[N:61]1

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 574072TrimethylboroxineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 24785465HCID 24785465, compound

Product 1

HCID 86618172HCID 86618172, compound

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of trimethylboroxine (83 mg), tris(dibenzylideneacetone)dipalladium (10 mg), Xantphos (18 mg), potassium carbonate (165 mg) and 3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-5-methyl-4-trifluoromethylthiopyrazole (250 mg) in dioxane was heated in a microwave for 20 minutes at 130° C. in a 10 ml sealed Pyrex glass tube. The reaction mixture was cooled to room temperature then diluted with ethyl acetate and filtered over Celite. The organic filtrate was washed with water, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to give a residue that was purified by chromatography (SiO2, heptane/EA) to afford the title compound as a white solid. MS (ES): M/Z [M+NH4]=417. 1H NMR: (400 MHz, CDCl3): 2.13 (s, 3H), 2.26 (s, 3H), 7.60 (bs, 1H) and 7.73 (bs, 1H). 19F NMR (376 MHz, CDCl3): −44.25 (s, 3F) and −63.63 (s, 3F).

Workup

  1. customsealed Pyrex glass tube
  2. filtrationfiltered over Celite
  3. washThe organic filtrate was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto give a residue that
  8. customwas purified by chromatography (SiO2, heptane/EA)

Sources & evidence

ORD record
ord-c44031ebf3f84c4e94461eaabba9a91a
Source dataset
uspto-grants-2013_05
Patent number
US08445519B2

Reaction notes

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