Dichloromethane → 5-{[4-(4-Butyl-phenylethynyl)-benzyl]-cyclopentylmethylamino}-2-fluoro-benzoic acid methyl ester

Participants

Reaction Conditions

Reaction Steps

A solution of methyl 5-({4-[(4-butylphenyl)ethynyl]benzyl}amino)-2-fluorobenzoate (800 mg, 1.93 mmol) in DCE (16 mL) was treated with cyclopentanecarboxaldehyde (Aldrich, 283 mg, 2.89 mmol) then with sodium triacetoxyborohydride (1.22 g, 5.78 mmol). The resulting mixture was stirred at 70° C. for 2 h. The reaction mixture was allowed to cool down, dichloromethane (40 mL) was added and the organic layer was washed twice with water and with brine, dried over magnesium sulfate, filtered and concentrated. Purification by flash chromatography on silicagel afforded the title compound as a colorless oil (590 mg, 60%). HPLC, Rt: 6.47 min (purity: 97.1%), LC/MS, M+(ESI): 498.1. 1H NMR (CDCl3) δ: 7.42 (m, 4H), 7.22 (m, 1M), 7.14 (m, 4H), 6.92 (m, 1H), 6.75 (m, 1H), 4.55 (s, 2H), 3.89 (s, 3H), 3.33 (d, 2H), 2.60 (t, J=7.7 Hz, 2H), 2.29 (m, 1H), 1.65 (m, 2H), 1.70-1.46 (m, 6H), 1.42-1.15 (m, 6H), 0.91 (t, J=7.3 Hz, 3H).

Provenance & Evidence