HCID 58345572, compound → HCID 58345590, compound

HRID 2381243Notes

Reaction equation

HRID 2381243 reaction equation
[CH2:1]([O:8][C:9]1[C:20]([O:21][CH3:22])=[CH:19][C:12]([C:13]([O:15][CH:16]([CH3:18])[CH3:17])=[O:14])=[C:11]([C:23](=[O:31])[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2Br)[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cu][C:33]#[N:34]>[C-]#N.C([N+](CC)(CC)CC)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].C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].O1CCOCC1>[CH2:1]([O:8][C:9]1[C:20]([O:21][CH3:22])=[CH:19][C:12]([C:13]([O:15][CH:16]([CH3:18])[CH3:17])=[O:14])=[C:11]([C:23](=[O:31])[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[C:33]#[N:34])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 2

HCID 58345572HCID 58345572, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 58345590HCID 58345590, compoundYield 77.3%

Reagents, catalysts & solvents 4

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 3014735Tetraethylammonium cyanideCatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

A mixture of isopropyl 4-benzyloxy-2-(2-bromobenzoyl)-5-methoxybenzoate (reference example 11-9) (600 mg), copper(I) cyanide (445 mg), tris(dibenzylideneacetone)dipalladium (114 mg), tetraethylammonium cyanide (194 mg), 1,1′bis(diphenylphosphino)ferrocene (206 mg) and 1,4-dioxane (73 mL) was stirred under reflux overnight. The mixture was passed through a layer of Celite (registered mark). The filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: 5%-30% ethyl acetate/hexane, gradient elution) to give the title compound (412 mg).

Workup

  1. temperatureunder reflux overnight
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (eluent: 5%-30% ethyl acetate/hexane, gradient elution)

Sources & evidence

ORD record
ord-bf8064cf2b3d4656b9f239a03d99648f
Source dataset
uspto-grants-2012_09
Patent number
US08258162B2

Reaction notes

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