Application background and overview of 2-(aminomethyl)-5-bromopyridine dihydrochloride
2-(Aminomethyl)-5-bromopyridine dihydrochloride is an organic heterocyclic compound that can be used as a pharmaceutical synthesis intermediate.
Application and preparation of 2-(aminomethyl)-5-bromopyridine dihydrochloride
The preparation of 2-(aminomethyl)-5-bromopyridine dihydrochloride is as follows:
Methoxypyridine
Dissolve 5-bromo-2-cyanopyridine (1.4 g, 7.7 mmol), the compound represented by formula 3 pyridinecarbonitrile-A, into tetrahydrofuran (20 ml), and slowly add borane (276 mg, 3 equivalents) , 23mmol), then stir at room temperature for about 16 hours, quench with water, stir at 60°C for about 20 minutes, add 2N hydrochloric acid (10ml) and continue stirring for about 20 minutes, cool to room temperature, add 2N sodium hydroxide solution to adjust the pH to 8 , concentrate to remove water, dissolve the solid with a mixed solution of methanol/dichloromethane = 10/1, filter, and concentrate to obtain 3-b compound 2-(aminomethyl)-5-bromopyridine (1.4 g, 7.5 millimole, yield 98%), yellow oil, LC-MS: M/Z=187, 189 (M+H)+. 2-(Aminomethyl)-5-bromopyridine is salted with hydrochloric acid to obtain 2-(aminomethyl)-5-bromopyridine dihydrochloride.
Applications of 2-(aminomethyl)-5-bromopyridine dihydrochloride
2-(Aminomethyl)-5-bromopyridine dihydrochloride can undergo the following reactions:
Dissolve 2-(aminomethyl)-5-bromopyridine dihydrochloride (1.4 g, 7.5 mmol) in dichloromethane (20 mL), then slowly add DIPEA (1.8 g, 2 equiv, 14 mmol) and isobutyryl chloride (954 mg, 1.3 equiv., 9.0 mmol), stir at room temperature for about 3 hours, add dichloromethane, and then wash with protective brine. The organic layer is dried over anhydrous sodium sulfate and passed through a silica gel column. Chromatography purified the compound shown in Formula 3-C, N-((5-bromo-2-pyridyl)methyl)-2-methyl-propionamide (350 mg, 1.36 mmol, yield 20%) , brown solid, LC-MS: M/Z=257, 259 (M+H)+
