Ethyl Acetate → HCID 59443042, compound

HRID 1959146Notes

Reaction equation

HRID 1959146 reaction equation
Cl[C:2]1[C:7]2[CH:8]=[CH:9][C:10]([N+:12]([O-:14])=[O:13])=[CH:11][C:6]=2[O:5][C:4]([CH3:16])([CH3:15])[N:3]=1.[F:17][C:18]1[CH:23]=[CH:22][C:21](B(O)O)=[CH:20][CH:19]=1.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>C(COC)OC.[Cl-].[Na+].O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[F:17][C:18]1[CH:23]=[CH:22][C:21]([C:2]2[C:7]3[CH:8]=[CH:9][C:10]([N+:12]([O-:14])=[O:13])=[CH:11][C:6]=3[O:5][C:4]([CH3:16])([CH3:15])[N:3]=2)=[CH:20][CH:19]=1

Participants

8

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 2856454-Fluorophenylboronic acidHCID 59443043HCID 59443043, compound

Product 1

HCID 59443042HCID 59443042, compound

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 80711,2-DimethoxyethaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A mixture of the compound obtained in (1) described above (1.75 g), 4-fluorophenylboronic acid (1.53 g), potassium carbonate (1.55 g) and a catalytic amount of [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) in dimethoxyethane (30 mL) was heated under reflux under nitrogen atmosphere overnight. After cooling to room temperature, to the reaction mixture was added ethyl acetate (30 mL) and saturated brine (30 mL). The organic layer was separated and washed with brine, dried over sodium sulfate and concentrated in vacuo. The residue is purified by flush chromatography on silica gel (petroleum ether/ethyl acetate=10/0 to 10/1) to give the titled compound (1.0 g) as a yellow powder.

Workup

  1. additionA mixture of the compound
  2. temperatureunder reflux under nitrogen atmosphere overnight
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue is purified
  8. customby flush chromatography on silica gel (petroleum ether/ethyl acetate=10/0 to 10/1)

Sources & evidence

ORD record
ord-d7f8c487f2924efca98271e530ac26e3
Source dataset
uspto-grants-2013_04
Patent number
US08410166B2

Reaction notes

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