6-Amino-2,2-dimethyl-benzo[1,3]dioxin-4-one → HCID 57554502, compound

Participants

Reaction Steps

The title compound was prepared following procedure described in example 1, step c) from 4-{[4-(trifluoromethyl)phenyl]ethynyl}benzaldehyde (1.22 g; 4.43 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 (855 mg; 4.43 mmol). Purification of the crude (2.6g) by precipitation in DCM upon addition of pentane gave 590 mg (30%) of the title compound as a brown solid. HPLC, Rt: 4.76 min (purity: 76.2%). LC/MS, M+(ESI): 452, M−(ESI): 450.1, 1H NMR (CDCl3) δ 7.59 (s, 4H), 7.51 (d, J=7.5 Hz, 2H), 7.34 (d, J=7.7 Hz, 2H), 7.15 (s, 1H), 6.80 (m, 2H), 4.34 (s, 2H), 1.68 (s, 6H). Purification of the filtrate by flash chromatography on silicagel (EtOAc/c-Hex 10:90 then 20:80) gave another 420 mg of the title compound (21%) as a yellow powder.

Provenance & Evidence