Sodium Hydroxide → Methyl 5-{[{4-[(4-butylphenyl)ethynyl]benzoyl}(hexyl)amino]methyl}-2-fluorobenzoate

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-(4-butylphenylethynyl)benzoic acid (312 mg; 1.12 mmol) in DCM (15 mL) were added HOBT (181 mg; 1.35 mmol), EDC-HCl (258 mg; 1.35 mmol) and DIEA (362 mg; 2.81 mmol). The mixture was stirred for 10 min at room temperature under N2 atmosphere before the addition of methyl 2-fluoro-5-[(hexylamino)methyl]benzoate (300 mg; 1.12 mmol). The reaction mixture was then stirred at 25° C. under N2 atmosphere overnight. It was diluted in DCM (100 mL) and poured into NaOH (1N, 75 mL). The organic layer was washed with brine (100 mL), dried over magnesium sulfate, filtrated and the solvent was removed under reduced pressure. Purification by flash chromatography using silicagel (c-Hex/EtOAc, gradient from 9:1 to 1:1) gave 350 mg (59%) of the title compound as a white powder. HPLC, Rt: 6.19 min (purity=99.7%). LC/MS, M+(ESI): 528.3. 1H NMR (CDCl3) δ: 7.91 (m, 1H), 7.55 (m, 3H), 7.41 (m, 4H), 7.15 (m, 3H), 4.72 (m, 1H), 4.50 (m, 1H), 3.93 (s, 3H), 3.42 (m, 1H), 3.15 (m, 1H), 2.61 (t, J=5.5 Hz, 2H), 1.59 (qt, J=7.7 Hz, 2H), 1.2 (m, 10H), 0.92 (t, J=7.3 Hz, 3H), 0.8 (m, 3H).

Provenance & Evidence