Hexanal → Methyl 5-[{4-[(4-tert-butylphenyl)ethynyl]benzyl}(hexyl)amino]-2-fluorobenzoate

Participants

Reaction Steps

The title compound was prepared following procedure described in Example 49, step a) from 4-[(4-tert-butylphenyl) ethynyl]benzaldehyde (500 mg; 1.91 mmol, intermediate which may be prepared according to methods disclosed in EP0310378.0.7) and methyl 5-amino-2-fluorobenzoate (322 mg; 1.91 mmol) and hexanal (Aldrich, 690 μl; 5.72 mmol). Purification of the crude (700 mg) by preparative HPLC using a X-Terra column afforded 440 mg (46%) of the title compound as a red oil. HPLC, Rt: 6.46 min (purity=89.9%). LC/MS: M+(ESI): 500.3. 1H NMR (CDCl3) δ: 7.57 (d, J=1.9 Hz, 2H), 7.54 (d, J=2.3 Hz, 2H), 7.45 (d, J=8.3 Hz, 2H), 7.35-7.20 (m, 3H), 7.04 (t, J=9.6 Hz, 1H), 6.85 (m, 1H), 4.61 (s, 2H), 4.00 (s, 3H), 3.47 (t, J=7.72 Hz, 2H), 1.70 (m, 2H), 1.39 (s, 15H), 0.99 (t, J=6.6Hz, 3H).

Provenance & Evidence