The origin of a common compound about 5-Bromo-2-methoxynicotinaldehyde

At the same time, in my other blogs, there are other synthetic methods of this type of compound,103058-87-3, 5-Bromo-2-methoxynicotinaldehyde, and friends who are interested can also refer to it.

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.103058-87-3, name is 5-Bromo-2-methoxynicotinaldehyde, molecular formula is C7H6BrNO2, molecular weight is 216.032, as common compound, the synthetic route is as follows.Application In Synthesis of 5-Bromo-2-methoxynicotinaldehyde

5-Bromo-2-methoxynicotinaldehyde (0.529 g, 2.450 mmol) and (2S,3S,4S,5S)-tert-butyl 4-amino-3-(tert-butyl)-1-(cyclohexanecarbonyl)-5-phenylpyrrolidine-2-carboxylate (Example 25B, 1 g, 2.333 mmol) were mixed in methanol (12 mL), and the reaction was stirred at room temperature for 1 hour. Sodium cyanoborohydride (0.740 g, 11.78 mmol) was then added in one portion, and the reaction continued to stir at room temperature for 1.5 days. After this time, the solvent was removed in vacuo, and the residue was taken up in 100 mL water and 100 mL CH2Cl2 and transferred to a separatory funnel. The separatory funnel was shaken, the phases were separated, and the aqueous layer was extracted twice more with CH2Cl2 (100 mL each time). The combined organics were dried over Na2SO4, filtered, and concentrated in vacuo. Silica gel chromatography, eluting with 5 to 30% ethyl acetate-heptanes, provided the impure title compound, 1.02 g. The material was taken directly into the next reaction without additional purification. 1H NMR (400 MHz, dimethyl sulfoxide-d6) delta ppm 8.00 (m, 1H), 7.59 (m, 2H), 7.40-7.19 (m, 4H), 5.17 (d, J=6.9 Hz, 1H), 4.40 (d, J=2.7 Hz, 1H), 3.68 (s, 3H), 3.41-3.21 (m, 3H), 2.26 (m, 1H), 2.19 (m, 1H), 1.68-1.02 (m, 10H), 1.43 (s, 9H), 0.98 (s, 9H); MS (ESI+) m/z 628.0 (M+H)+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,103058-87-3, 5-Bromo-2-methoxynicotinaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; AbbVie S.a.r.l.; Galapagos NV; Altenbach, Robert J.; Bogdan, Andrew; Couty, Sylvain; De Lemos, Elsa; Desroy, Nicolas; Duthion, Beranger; Gfesser, Gregory A.; Greszler, Stephen N.; Housseman, Christopher Gaetan; Koenig, John R.; Kym, Philip R.; Liu, Bo; Scanio, Marc J.; Searle, Xenia; Wang, Xueqing; Yeung, Ming C.; Zhao, Gang; (263 pag.)US2018/99931; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem