With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.113118-81-3, name is 5-Bromonicotinaldehyde, molecular formula is C6H4BrNO, molecular weight is 186.0061, as common compound, the synthetic route is as follows.Computed Properties of C6H4BrNO
Intermediate 22(E)-3-Bromo-5-(3-methoxystyryl)pyridine. To a solution of diethyl 3- methoxybenzylphosphonate (5 g, 19.36 mmol) in dimethylformamide (50 mL) at room temperature was added sodium methoxide (2.092 g, 38.7 mmol) and 18-Crown- 6 (2.047 g, 7.74 mmol). After stirring at room temperature for 5 min, the reaction was cooled to 0C and treated with 5-bromonicotinaldehyde (4.32 g, 23.23 mmol) as a solid in one portion. The ice bath was removed and the reaction stirred at room temperature for 2 h. The reaction was poured into water (500 mL) with vigorous stirring. The resulting suspension was extracted with diethyl ether, washed with water (3X), then brine, dried over magnesium sulfate, and concentrated to an oil which crystallized upon standing. The solid was triturated with a minimum of ethanol (ca. 12 mL) and placed in the freezer for 72 h. The resulting solid was broken up with a spatula, collected by filtration, and rinsed with a minimum of cold ethanol to give 3.79 g (68%) as a white crystalline solid. ¾-NMR (CDC13> 500MHz) delta 8.64 (d, J=1.8, IH), 8.57 (d, J=2.1, IH), 8.00 (dd, J=2.1, 1.8, IH), 7.33 (dd, J=7.9, 7.9, IH), 7.10-7.20 (m, 2H), 7.07 (m, IH), 7.01 (d, J=16.5, IH), 6.91 (dd, J=7.6, 2.1, IH), 3.88 (s, 3H). 13C-NMR (CDC13, 126 MHz) delta 160.1, 149.5, 146.7, 137.7, 135.1, 134.8, 132.4, 130.0, 123.7, 121.1, 1 19.6, 1 14.4, 112.2, 55.4. Mass spec: 290.14 (MH)+..
At the same time, in my other blogs, there are other synthetic methods of this type of compound,113118-81-3, 5-Bromonicotinaldehyde, and friends who are interested can also refer to it.
Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; DEGNAN, Andrew P.; HUANG, Hong; SNYDER, Lawrence B.; YANG, Fukang; GILLMAN, Kevin W.; PARKER, Michael F.; WO2012/64603; (2012); A1;,
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