HCID 86587734, compound → HCID 73710678, compound

HRID 1796697Notes

Reaction equation

HRID 1796697 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]2[C:13]([C:14](=[O:16])[CH:15]=1)=[CH:12][CH:11]=[C:10]([NH:17][C:18](=[O:23])[C:19]([F:22])([F:21])[F:20])[C:9]=2[CH2:24][CH:25]=[CH2:26])=[O:5])[CH3:2]>C(Cl)Cl.CC#N.CC#N.Cl[Pd]Cl>[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]2[C:13]([C:14](=[O:16])[CH:15]=1)=[CH:12][CH:11]=[C:10]([NH:17][C:18](=[O:23])[C:19]([F:20])([F:21])[F:22])[C:9]=2[CH:24]=[CH:25][CH3:26])=[O:5])[CH3:2]

Participants

4

Reactant 1

HCID 86587734HCID 86587734, compound

Product 1

HCID 73710678HCID 73710678, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 6093782Bis(acetonitrile)dichloropalladiumCatalystHCID 6344DichloromethaneSolvent

Procedure

To 8-allyl-4-oxo-7-(2,2,2-trifluoro-acetylamino)-4H-chromene-2-carboxylic acid ethyl ester (12.2 g, 32 mmole) in 500 mL of methylene chloride was added 1.5 g (5.8 mmole) of bis(acetonitrile)palladium (II) chloride. The mixture was refluxed under nitrogen for 24 hours. Upon cooling to room temperature, the mixture was filtered through 75 g of silica gel, with additional methylene chloride as needed to fully elute the product. Concentration in vacuum gave 10.4 g of the title compound as a yellow solid, m.p. 140–141° C.

Workup

  1. temperatureThe mixture was refluxed under nitrogen for 24 hours
  2. filtrationthe mixture was filtered through 75 g of silica gel, with additional methylene chloride
  3. washto fully elute the product
  4. concentrationConcentration in vacuum

Sources & evidence

ORD record
ord-06f43a3c96fe41f7a018ac2f547cf505
Source dataset
uspto-grants-2006_04
Patent number
US07030245B2

Reaction notes

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