Water → N-(2-(5-bromo-7-chlorobenzofuran-2-yl)ethyl)-2,2-dimethoxyethanamine

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Reaction Conditions

Reaction Steps

To a solution of the product of Example 84, step C (2.0 g, 4.65 mmol) in dioxane (10 mL) was added 2,2-dimethoxyethanamine (1.47 g, 13.95 mmol). The reaction mixture was heated to 90° C. for 3 h, cooled to ambient temperature, treated with water (20 mL) and extracted with dichloromethane (3×20 mL). The combined organic extracts were washed with brine, dried over Na2SO4, filtered, and the filtrate concentrated in vacuo. Purification by flash column chromatography (SiO2, hexanes/ethyl acetate) gave N-(2-(5-bromo-7-chlorobenzofuran-2-yl)ethyl)-2,2-dimethoxyethanamine (1.27 g, 75%) as a colorless oil: 1H NMR (CDCl3, 400 MHz) δ 7.49 (d, J=1.8 Hz, 1H), 7.33 (d, J=1.8 Hz, 1H), 6.44 (s, 1H), 4.48 (t, J=5.5 Hz, 2H), 3.38 (s, 6H), 3.09-2.94 (m, 4H), 2.78 (d, J=5.4 Hz, 2H).

Provenance & Evidence