Category: 149806-06-4

Synthetic Route of 149806-06-4, 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.149806-06-4, name is 6-Bromonicotinaldehyde, molecular formula is C6H4BrNO, molecular weight is 186.01, as common compound, the synthetic route is as follows.

6-bromo-pyridine-3-carbaldehyde (5 g, 26.9 mmol, 1.0 eq.) and 4-ethyl-piperidine was dissolved in dichloromethane (100 ml), stirred for 2 hours, acetic acid was added portionwise inside borohydride sodium (6.2 g, 29.2 mmol, 1.1 eq). After 16 hours of reaction, an aqueous solution of sodium hydroxide was added thereto 2 mol/L to adjust the PH to alkaline, extracted with dichloromethane, and concentrated under reduced pressure to give a white solid of 1-(6-bromopyridin-3-yl)methyl-4-ethylpiperidine (6.98g, yield: 91.4%).

The chemical industry reduces the impact on the environment during synthesis 149806-06-4, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Guangzhou Kaisheng Beite Pharmaceutical Co., Ltd.; Cai, Xiong; Qian, Changgeng; Liu, Bin; Li, Junqi; Lin, Mingsheng; Qing, Yuanhui; Weng, Yunwo; Wang, Yanyan; Xue, Weicai; You, Huajin; Zhou, Shiqing; (67 pag.)CN105622638; (2016); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 149806-06-4 ,Some common heterocyclic compound, 149806-06-4, molecular formula is C6H4BrNO, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

Reagents: i) Methaneboronic acid, 16%; ii) Ethyl acrylate ; iii) NaOH, 35% yield for the last two steps.LC/MS data of 2805 – Calculated MW is 177; observed (the peak at 11.2 min, TIC): 178 [M+H].Gradient: 0-5 min: 5% ACN; 5-20 min: 5-10% ACN; 20-30 min: 10-98%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,149806-06-4, its application will become more common.

Reference:
Patent; TRUSTEES OF TUFTS COLLEGE; WO2008/16968; (2008); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 149806-06-4, 6-Bromonicotinaldehyde, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound, Quality Control of 6-Bromonicotinaldehyde, blongs to pyridine-derivatives compound. Quality Control of 6-Bromonicotinaldehyde

To a solution of compound 5 (10 g, 54 mmol, 1 eq) in DCM (170 mL) was added compound 6 (7.4 g, 65 mmol, 1.2 eq). The mixture was stirred at rt for 30 minutes, then NaBH(OAc)3 (17.1 g, 81 mmol, 1.5 eq) was added portion wise. The mixture was stirred at rt for 12 h. After completion, the mixture was diluted with DCM (300 mL) and 2N NaOH (100 mL). The organic layer was separated and the aqueous layer was extracted with DCM (100 mL). The combined organic layers were dried over sodium sulfate, concentrated and purified by silica column chromatography to give the desired product (7 g, 46%). NMR (300 MHz, CDCb) delta 8.30 (s, 1 H), 7.55 (d, J= 8.1 Hz, 1 H), 7.44 (d, J= 8.1 Hz, 1 H), 3.49 (s, 2 H), 2.55- 2.48 (m, 10 H), 1.12 (t, J= 7.2 Hz, 3 H). LCMS: (M+H)+: 283.9.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,149806-06-4, 6-Bromonicotinaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; BEIJING XUANYI PHARMASCIENCES CO., LTD.; SONG, Yuntao; CHEN, Xiaoqi; (188 pag.)WO2019/35008; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem