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.Application In Synthesis of 5-Bromonicotinaldehyde
To a mixture of 5-bromopyridine-3-carbaldehyde (XXXVIII) (6.00 g, 32.26 mmol, 1.0 eq), 3,3-difluoropyrrolidine (5.56 g, 38.71 mmol, 1.20 eq) and TEA (5.39 mL, 38.71 mmol, 1.2 eq) in DCE (200 mL) was stirred at room temperature for 30 mm, then added sodium triacetoxyborohydride (10.25 g, 48.38 mmol, 1.50 eq) in one portion at room temperature under N2. The mixture was stirred at room temperature for 6 h. TLC showed the reaction was complete. The reaction was quenched with iN NaOH (100 mL), extracted with DCE (100 mL x 2). The combined organic layers were washed with brine (100 mL), dried and concentrated. The residue was purified by silica gel chromatography (column height: 50 mm, diameter: 50 mm, 300-400 mesh silica gel, DCMIMeOH=3 0/1 -*20/1) to give 3 -bromo-5 -((3,3 -difluoropyrrolidin- 1- yl)methyl)pyridine (XL): Yellow oil (8.00 g, 28.9 mmol, 89.5% yield). ?H NMR (CDC13, 400 MHz) ppm 2.30 (spt, J=7.2Hz. 2H), 2.75 (t, J=6.8Hz, 2H), 2.91 (t, J13.2Hz, 2H), 7.85 (s, 1H), 8.45 (s, 1H), 8.59 (d, J=2Hz, 1H); ESIMS found for C,0H,,BrF2N2 m/z 277.0 (M+H).
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; SAMUMED, LLC; KC, Sunil Kumar; WALLACE, David Mark; CAO, Jianguo; CHIRUTA, Chandramouli; HOOD, John; (271 pag.)WO2017/24026; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem