4-[(4-Methoxyphenyl)ethynyl]benzaldehyde → 6-({4-[(4-methoxyphenyl)ethynyl]benzyl}amino)-2,2-dimethyl-4H-1,3-benzodioxin-4-one

Participants

Reaction Steps

The title compound was prepared following procedure described in Example 1, step c) from 4-[(4-methoxyphenyl)ethynyl]benzaldehyde (1.31 g; 5.53 mmol, intermediate which may be obtained according to methods disclosed in EP03103780.7) and 6-amino-2,2-dimethyl-benzo[1,3]dioxin-4-one (1.07 g; 5.53 mmol). The crude (1.7 g) was purified by recrystallisation from MeOH/EtOAc to give 1.23 g (54%) of the title compound as a yellow powder. HPLC, Rt: 4.77 min (purity: 77%). 1H NMR (CDCl3) δ: 7.46 (m, 4H), 7.31 (d, J=7.9 Hz, 2H), 7.15 (d, J=2.6 Hz, 1H), 6.85 (d, J=8.5 Hz, 2H), 6.78 (m, 2H), 4.30 (s, 2H), 3.81 (s, 3H), 1.68 (s, 6H).

Provenance & Evidence