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With ammonium hydroxide In tetrahydrofuran at 20℃; for 18 h;
A mixture of 3-bromomethyl-2,6-dichloroisonicotinic acid ethyl ester (13.4 g, 42.7 mmol), tetrahydrofuran (100 ml_), and ammonium hydroxide (300 ml. of 28-30percent ammonia) is stirred at room temperature for 18 h. The solvents are then removed by rotary evaporation. The nearly dry solid is treated with a small amount of water. The salmon-colored solid is isolated by filtration, washed with small amounts of water and then diethyl ether, and dried under vacuum. Filtration of the cooled filtrate yields additional salmon-colored solid (7.47g, 36.8 mmol, 86percent). MS(ESI) m/z 203.2 (M+1 ). 1H NMR (400 MHz, DMSOd6) δ ppm 9.29 (br. s., 1 H), 7.83 (s, 1 H), 4.45 (s, 2 H).
Reference：
[1] Patent: WO2009/150230, 2009, A1, . Location in patent: Page/Page column 180-181
[2] Journal of Medicinal Chemistry, 2010, vol. 53, # 15, p. 5422 - 5438
With N-Bromosuccinimide; acetic acid; dibenzoyl peroxide; In tetrachloromethane; at 60.0℃; for 5.0h;
To a mixture of <strong>[137520-99-1]2,6-dichloro-3-methylisonicotinic acid ethyl ester</strong> (10.0 g, 42.7 mmol), Example 7E and acetic acid (2.69 g, 44.9 mmol) in carbon tetrachloride (147 ml.) are added lambda/-bromosuccinimide (8.36 g, 47.0 mmol) and then benzoyl peroxide (1.03 g, 4.27 mmol). The mixture is stirred in oil bath at 60 0C under heat lamp for 5 h. The mixture is then cooled to room temperature. About half of the solvent is removed by rotary evaporation. The white succinimide solid is removed by filtration. The overweight filtrate (17 g for a theoretical 13.4 g, 42.7 mmol) is concentrated under reduced pressure and used as a crude immediately for the next step. MS(ESI) m/z 313.99. 1H NMR (400 MHz1CDCI3) delta ppm 7.72 (s, 1 H), 4.99 (s, 2 H), 4.48 (q, J=7.16 Hz, 2 H), 1.46 (t, J=7.07 Hz, 3 H).
With ammonium hydroxide; In tetrahydrofuran; at 20℃; for 18.0h;
A mixture of 3-bromomethyl-2,6-dichloroisonicotinic acid ethyl ester (13.4 g, 42.7 mmol), tetrahydrofuran (100 ml_), and ammonium hydroxide (300 ml. of 28-30% ammonia) is stirred at room temperature for 18 h. The solvents are then removed by rotary evaporation. The nearly dry solid is treated with a small amount of water. The salmon-colored solid is isolated by filtration, washed with small amounts of water and then diethyl ether, and dried under vacuum. Filtration of the cooled filtrate yields additional salmon-colored solid (7.47g, 36.8 mmol, 86%). MS(ESI) m/z 203.2 (M+1 ). 1H NMR (400 MHz, DMSOd6) delta ppm 9.29 (br. s., 1 H), 7.83 (s, 1 H), 4.45 (s, 2 H).
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