Benzene, 1-chloro-4-ethynyl- → 4-[(4-chlorophenyl)ethynyl]-N-(3-cyclopentylpropyl)-N-(2,2-dimethyl-4-oxo-4H-1,3-benzodioxin-7-yl)benzamide

Participants

Reaction Steps

The title compound was prepared following procedure described in example 26, step d) from 4-bromo-N-(3-cyclopentylpropyl)-N-(2,2-dimethyl-4-oxo-4H-1,3-benzodioxin-7-yl)benzamide (437 mg, 0.90 mmol) and 4-chlorophenylacetylene (Apollo, 118 mg, 0.86 mmol). Purification by flash chromatography on silicagel (EtOAc/c-Hex 20:80) gave 373 mg (80%) of the title compound as a white foam. HPLC, Rt: 6.03 min (purity: 93.6%). LC/MS, M+(ESI): 541.9. 1H NMR (CDCl3) δ: 7.78 (d, J=8.3 Hz, 1H), 7.24-7.45 (m, 8H), 6.74 (dd, J=8.4, 2.0 Hz, 1H), 6.58 (d, J=1.9 Hz, 1H), 3.90 (t, J=7.6 Hz, 2H), 1.46-1.86 (m, 9H), 1.40 (s, 6H), 1.36 (m, 2H), 1.03 (m, 2H).

Provenance & Evidence