Cesium carbonate → HCID 68700286, compound

HRID 14479Notes

Reaction equation

HRID 14479 reaction equation
[CH2:1]([O:8][C:9](=[O:36])[N:10]([CH2:33][CH:34]=[CH2:35])[C:11]1[C:20](Br)=[C:19]2[C:14]([C:15](=[O:32])[C:16]([C:25]3[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=3)=[C:17]([CH:22]([CH3:24])[CH3:23])[O:18]2)=[CH:13][CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[C].[C]>C(#N)C.C(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]>[CH2:1]([O:8][C:9]([N:10]1[C:11]2[C:20](=[C:19]3[O:18][C:17]([CH:22]([CH3:24])[CH3:23])=[C:16]([C:25]4[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=4)[C:15](=[O:32])[C:14]3=[CH:13][CH:12]=2)[C:34]([CH3:35])=[CH:33]1)=[O:36])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 68700441HCID 68700441, compoundHCID 178420941HCID 178420941, compound

Product 1

HCID 68700286HCID 68700286, compound

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of allyl-[8-bromo-3-(4-chlorophenyl)-2-isopropyl-4-oxo-4H-chromen-7-yl]carbamic acid benzyl ester (0.094 g, 0.166 mmol), tetrakis(triphenylphosphine)palladium (0) (0.01 g, 0.0086 mmol, 5 mol %) and cesium carbonate (0.27 g, 0.83 mmol, 5 eq.) in acetonitrile (4 ml) and methylene chloride (1 ml) is irradiated in a microwave instrument at 100° C. for 20 min. The mixture is filtered through Celite filter aid, and the pad of Celite is washed with methylene chloride, followed by ethyl acetate. The combined filtrates are evaporated in vacuo, and the residue is purified by flash chromatography (15% ethyl acetate in cyclohexane) to afford a yellow solid. LC-MS analysis suggests, that the product is a mixture of carbon-carbon double bond isomers in a 1.7:1 ratio.

Workup

  1. customis irradiated in a microwave instrument at 100° C. for 20 min
  2. filtrationThe mixture is filtered through Celite
  3. filtrationfilter aid
  4. washthe pad of Celite is washed with methylene chloride
  5. customThe combined filtrates are evaporated in vacuo
  6. customthe residue is purified by flash chromatography (15% ethyl acetate in cyclohexane)
  7. customto afford a yellow solid

Sources & evidence

ORD record
ord-1456953de32345ee96335a8be154cf74
Source dataset
uspto-grants-2010_06
Patent number
US07732435B2

Reaction notes

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