Cyclopentylacetylene → HCID 57804210, compound

HRID 2102906Notes

Reaction equation

HRID 2102906 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7](Br)=[CH:6][C:5]=1[F:11].[C:13]([CH:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1)#[CH:14]>C(N(CC)CC)C.[Cu](I)I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH:15]1([C:13]#[C:14][C:7]2[CH:8]=[CH:9][C:4]([C:3]([O:2][CH3:1])=[O:12])=[C:5]([F:11])[CH:6]=2)[CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

6

Reactant 2

HCID 136725CyclopentylacetyleneHCID 113453114-Bromo-2-fluoro-benzoic acid methyl ester

Product 1

HCID 57804210HCID 57804210, compoundYield 93.4%

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8471TriethylamineSolvent

Conditions

Temperature
80 °C

Procedure

4-Bromo-2-fluorobenzoic acid methyl ester (1.0 g, 4.0 mmol) was dissolved in triethylamine (5 mL). To the mixture was added copper iodide (38 mg, 5 mol %), followed by PdCl2(PPh3)2 (140 mg, 5 mol %) and ethynylcyclopentane (0.85 mL, 6.3 mmol). The mixture was heated in a sealed pressure tube at 80° C. for 3 hours. After completion of the reaction, the triethylamine was removed under vacuum and the residue was dissolved in EtOAc and filtered through Celite®. The organic layer was washed with water, brine, and dried (Na2SO4), filtered and the mixture concentrated under vacuum. The residue was purified using column chromatography on sililca using EtOAc-hexane (0-100% gradient) as eluent to give the product (0.92 g).

Workup

  1. customAfter completion of the reaction
  2. customthe triethylamine was removed under vacuum
  3. dissolutionthe residue was dissolved in EtOAc
  4. filtrationfiltered through Celite®
  5. washThe organic layer was washed with water, brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationthe mixture concentrated under vacuum
  9. customThe residue was purified

Sources & evidence

ORD record
ord-72225eb22cff47a4897bae73e31d2856
Source dataset
uspto-grants-2009_08
Patent number
US07576099B2

Reaction notes

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