HCID 68666323, compound → HCID 68666243, compound

HRID 1443414Notes

Reaction equation

HRID 1443414 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][C:17]=1Br)[C:5]([O:7]CC1C=CC=CC=1)=[O:6].[Br-].[CH:20]1([Zn+])[CH2:24][CH2:23][CH2:22][CH2:21]1>C1COCC1.CO.CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C.[Pd]>[F:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][C:17]=1[CH:20]1[CH2:24][CH2:23][CH2:22][CH2:21]1)[C:5]([OH:7])=[O:6]

Participants

7

Reactant 2

HCID 68666323HCID 68666323, compoundHCID 178419768HCID 178419768, compound

Product 1

HCID 68666243HCID 68666243, compound

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 178418851HCID 178418851, compoundCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 0.45 g (1.45 mmol) of benzyl 3-fluoro-4-bromobenzoate (0.45 g, 1.45 mmol) in 4.4 mL of 0.5 M cyclopentylzinc bromide solution in THF was treated with ˜5 mg of bis(tri-t-butylphosphine)palladium(0) and the resulting mixture was stirred at rt for 24 h. The reaction mixture was directly purified on a Biotage 40S cartridge using 1:1 hexanes/EtOAc as the eluant. A mixture of the resulting solid (0.27 g, 0.91 mmol) and 10% Pd/C in 5 mL of MeOH was stirred under 1 atm of H2 for 3 h. The reaction was filtered and concentrated. Purification by HPLC B afforded the title compound: 1H NMR δ 1.58-1.90 (m, 6H), 2.05-2.14 (m, 2H), 3.30 (m, 1H), 7.36 (t, J=7.7, 1H), 7.72 (dd, J=1.6, 10.5, 1H), 7.83 (dd, J=1.6, 8.0, 1H).

Workup

  1. customThe reaction mixture was directly purified on a Biotage 40S cartridge
  2. stirringwas stirred under 1 atm of H2 for 3 h
  3. filtrationThe reaction was filtered
  4. concentrationconcentrated
  5. customPurification by HPLC B

Sources & evidence

ORD record
ord-51aeaedb88264eaa85d438af546b9317
Source dataset
uspto-grants-2010_02
Patent number
US07659294B2

Reaction notes

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