HCID 68666323, compound → HCID 68666243, compound

Participants

Reaction Steps

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).

Provenance & Evidence