Cesium carbonate → HCID 63411309, compound

HRID 526690Notes

Reaction equation

HRID 526690 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5](I)=[CH:4][CH:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].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.[F:57][C:58]([F:69])([F:68])[C:59]1[CH:64]=[CH:63][C:62]([C:65](=[O:67])[CH3:66])=[CH:61][CH:60]=1>O1CCOCC1.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]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:66][C:65]([C:62]2[CH:63]=[CH:64][C:59]([C:58]([F:57])([F:68])[F:69])=[CH:60][CH:61]=2)=[O:67])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 125101-Chloro-4-iodobenzeneHCID 697311-(4-(Trifluoromethyl)phenyl)ethan-1-oneHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)

Product 1

HCID 63411309HCID 63411309, compound

Reagents, catalysts & solvents 2

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

A solution of 3 g of 1-Chloro-4-iodo-benzene, 9 g of Cs2CO3, 36 mg of Pd(dba)2 (Bis(dibenzylidenacetonpalladium), 72 mg of Xantphos (9,9-Dimethyl-4,5-bis(diphenylphosphino)xanthene) and 4.7 g of 1-(4-Trifluoromethyl-phenyl)ethanone in 45 ml of dioxane was heated under argon for 30 min at 150° C. by microwave irradiation. After cooling to room temperature and dilution with saturated aqueous sodium hydrogen carbonate solution the reaction mixture was filtered through a chem Elut® cartridge by eluting with ethyl acetate The solvents were removed under reduced pressure and the crude product was purified by chromatography on silica gel eluting with a gradient of n-heptane/ethyl acetate. The fractions containing the product were combined and the solvent evaporated under reduced pressure. Yield: 3.7 g.

Workup

  1. filtrationdilution with saturated aqueous sodium hydrogen carbonate solution the reaction mixture was filtered through a chem Elut® cartridge
  2. washby eluting with ethyl acetate The solvents
  3. customwere removed under reduced pressure
  4. customthe crude product was purified by chromatography on silica gel eluting with a gradient of n-heptane/ethyl acetate
  5. additionThe fractions containing the product
  6. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-bbfd08eff2e94351882fd45bc2db12cf
Source dataset
uspto-grants-2016_05
Patent number
US09346757B2

Reaction notes

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