Category: pyridine-derivatives

Application of 98555-51-2, Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 98555-51-2, name is 5-Bromopyridine-2,3-dicarboxylic acid. A new synthetic method of this compound is introduced below.

Example 12 2-Bromo-7-(4-fluoro-benzyl)-5,9-dihydroxy-pyrrolo[3,4-g]quinoline-6,8-dione; 1008 Following the literature procedure of M.-D. Le Bas et al. (Synthesis 2001, 16, p. 2495), 100 ml CCl4 was mixed with 250 ml of an aqueous NaOCl solution. To this mixture was added 40 mg of RuO2, followed by 3 g 3-bromoquinoline dissolved in 50 ml CCl4. Additional 30 ml portions of bleach were added at 2, 4, and 6 h. After 24 h, the aqueous layer was collected and acidified to pH 1 with 3N HCl. The aqueous layer was then extracted with ethyl acetate, dried over Na2SO4 and volatiles removed by evaporation to give the 1.7 g product as a yellow resin, (48% yield). 1H NMR and MS data matched that reported in the literature. The resulting anhydride, 1 g, was then carried through the previously reported multistep sequence to afford the corresponding cyano-ester. Dieckmann condensation between 80 mg (0.3 mmol) of the ester and 80 mg (3.6 mmol) of the imide utilizing 900 uL LiHMDS in 2 ml dry THF gave the crude product. After the typical work-up, approximately 60 mg (30%) of unpurified product was obtained as a yellow solid which was further refined by trituration with diethyl ether to provide 2 mg highly pure product 1008. 1H NMR (300 MHz, d6-DMSO) delta 9.20 (d, 1H), 9.05 (d, 1H) and 4.85 (s, 2H) ppm, MS=416.1 (M+H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,98555-51-2, 5-Bromopyridine-2,3-dicarboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; Cai, Zhenhong R.; Jabri, Salman Y.; Jin, Haolun; Lansdown, Rachael A.; Metobo, Samuel E.; Mish, Michael R.; Pastor, Richard M.; US2008/58315; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 905306-69-6, The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 905306-69-6, name is (5-Methoxypyridin-2-yl)methanamine. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 1-(5-methoxypyridin-2-yl)methanamine (138 mg, 1 mmol) and 2-chloro-3-methyl-7-(propan-2-yl)imidazo[5,1-f][1,2,4]triazin-4(3H)-one (90 mg, 0.4 mmol) in DMF (1.5 mL) was added DIEA (104 mg, 0.8 mmol). The reaction mixture was stirred at 50C for 10 h and purified by preparative HPLC (MeCN and H2O with 0.01% NH3.H2O as mobile phase) to give the titled compound (40 mg, yield 30 %).LC-MS (m/z) = 329 [M + H]+.1H-NMR (400 MHz, DMSO-d6): delta 1.40 (d, J = 7.2 Hz, 6H), 3.46-3.52 (m, 1H), 3.53 (s, 3H), 3.89 (s, 3H), 4.55 (d, J = 4.0 Hz, 2H), 6.07 (s, 1H), 7.27-7.31 (m, 2H), 7.75 (s, 1H), 8.26 (d, J = 2.4 Hz, 1H).

According to the analysis of related databases, 905306-69-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SUMITOMO DAINIPPON PHARMA CO., LTD.; FUJII, Yuki; FUJIWARA, Hiroaki; KAWASUMI, Muneo; IWAMA, Seiji; IKEDA, Tomoko; KIYOSHIGE, Saori; (219 pag.)WO2016/147659; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 183208-35-7, The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 183208-35-7, name is 5-Bromo-1H-pyrrolo[2,3-b]pyridine. This compound has unique chemical properties. The synthetic route is as follows.

EXAMPLE 1; Compound 1-1; 5-?-methyl-lH-pyrazol-4-yl)-3-(6-piperazin-l-ylpyrazin-2-v?-lH-pyrrolor2,3-b1pyridine; Step 1 : 5-bromo-l-(phenylsulfonylMH-pyrrolo[2,3-fr]rhoyridine; To a stirred solution of 5-bromo-lH-pyrrolo[2,3-Z>]pyridine (20.0 g, 102 mmol) in DMF (400 ml) at 0 0C was added NaH (60% mineral oil dispersion; 4.87 g, 122 mmol) slowly (CAUTION: GAS EVOLUTION). The reaction mixture was stirred at 0 C for 2 h. Benzenesulfonyl chloride (17.0 ml, 132 mmol) was added dropwise, and the reaction mixture was allowed to warm to ambient. After 1 hour the reaction mixture was cooled in an ice bath, and 100 mL of water was added slowly (CAUTION: GAS EVOLUTION, EXOTHERM). The reaction mixture was partitioned between ethyl acetate (500 mL) and brine (600 mL). The organic layer was washed with additional brine (500 mL), followed by saturated aqueous ammonium chloride (250 mL). The first and 3rd aqueous layers were combined and back- extracted with ethyl acetate (500 mL). The combined organics were dried over sodium sulfate, filtered and concentrated to a thick slurry. EtOAc (100 mL) was added, followed by hexanes (100 mL). The mixture was filtered, and the filter cake was rinsed with 1 :1 EtOAc/Hexanes (50 mL) to afford 5-bromo-l-(phenylsulfonyl)-lH-pyrrolo[2,3-£]pyridine as a grey solid. The filtrate can be concentrated and purified by silica gel chromatography (EtOAc/etaexanes gradient) to afford additional product. LRMS (ESI) calculated for C13H9BrN2O2S [M+H]+, 337.0; found 336.9.

According to the analysis of related databases, 183208-35-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK & CO., INC.; WO2009/54941; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 71255-09-9, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 71255-09-9, name is 2-Methoxynicotinaldehyde, molecular formula is C7H7NO2, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

A round bottom flask was charged with 0.44g (3.23mM) of 2-methoxy-3-pyridine carboxaldehyde (24), 1.24g (16.15mM) of ammonium acetate, and 0.61g (19.69mM) of sodium cyanoborohydride. The flask was then flushed with argon, and then 5OmL of dry MeOH was added by syringe. The reaction was stirred for 2 days, at which point the MeOH was evaporated off. 25mL of water was added, and the mixture was brought to pH 2 with cone. HCl. This was extracted twice with EtOAc to remove the alcohol side product. The mixture was brought to pH 10 using sodium hydroxide pellets, saturated with NaCl, and extracted twice with DCM and once with EtOAc. The combined organics were dried and evaporated to give 0.31g (69%) of 3-aminomethyl-2-methoxypy?dine (25).

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 71255-09-9, 2-Methoxynicotinaldehyde.

Reference:
Patent; PHARMACOPEIA , INC.; WO2008/60301; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 153034-94-7 ,Some common heterocyclic compound, 153034-94-7, molecular formula is C6H5FIN, 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.

Step 1: N-(2,4-dimethoxybenzyl)-4-iodo-5-methylpyridin-2-amine A solution of 2-fluoro-4-iodo-5-methylpyridine (85 g, 340 mmol) in 1-(2,4-dimethoxyphenyl)methanamine (270 mL, 1.68 mol) was allowed to stir at 110 C. overnight. The reaction mixture was allowed to cool to rt and diluted with EtOAc. A precipitate formed and was filtered and then washed with EtOAc. The solid was purified further by column chromatography to give N-(2,4-dimethoxybenzyl)-4-iodo-5-methylpyridin-2-amine (138 g, 50%).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 153034-94-7, 2-Fluoro-4-iodo-5-picoline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MILLENNIUM PHARMACEUTICALS, INC.; Bharathan, Indu T.; Blackburn, Chris; Ciavarri, Jeffrey P.; Chouitar, Jouhara; Cullis, Courtney A.; D’Amore, Natalie; Fleming, Paul E.; Gigstad, Kenneth M.; Gipson, Krista E.; Girard, Mario; Hu, Yongbo; Lee, Janice; Li, Gang; Rezaei, Mansoureh; Sintchak, Michael D.; Soucy, Francois; Stroud, Stephen G.; Vos, Tricia J.; Wong, Tzu-Tshin; Xu, He; Xu, Tianlin; Ye, Yingchun; US2015/225422; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 135795-46-9, name is 3-Amino-2-bromo-6-methoxypyridine, molecular formula is C6H7BrN2O, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below. Quality Control of 3-Amino-2-bromo-6-methoxypyridine

b N-(2-Bromo-6-methoxy-3-pyridinyl)-2-chloro-3-pyridinecarboxamide To a solution of 3-amino-2-bromo-6-methoxypyridine (2.7 g) in methylene chloride (20 ml) and pyridine (1 ml) was added 2-chloronicotinoyl chloride (2.2 g), and the resulting mixture was stirred 20 min. The mixture was then diluted with methylene chloride (100 ml), washed with water (100 ml), dried (anhydrous magnesium sulfate), and concentrated. The semisolid residue was saturated with hexane, filtered, and dried to give 4.1 g of product suitable for use in the next reaction.

With the rapid development of chemical substances, we look forward to future research findings about 135795-46-9.

Reference:
Patent; Boehringer Ingelheim Pharmaceuticals, Inc.; US5366972; (1994); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 16135-36-7, The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 16135-36-7, name is Methyl 4-aminonicotinate. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of dichloromethane (100 mL), 4-amino-nicotinic acid methyl ester (4.60 g, 30.2 [MMOL)] and diisopropylethyl amine (8.25 mL, 46.7 [MMOL),] was added (1-fluorocarbonyl-2-methyl-propyl)-carbamic acid benzyl ester (11.8 g, 46.7 [MMOL)] at room temperature and the mixture stirred overnight. The solvent was removed under reduced pressure and the residue purified by flash silica gel chromatography using hexane-EtOAc (stepwise gradient from 3: 1 to 1: 1) as eluents to obtain the desired amide of Formula 506, 4- (2-benzyloxycarbonylamino-3-methyl- butyrylamino)-nicotinic acid methyl ester (10.5 g, 90. 1%). MS [(CI)] M/E: 386.2.

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 16135-36-7, Methyl 4-aminonicotinate.

Reference:
Patent; CYTOKINETICS, INC.; SMITHKLINE BEECHAM CORPORATION; WO2003/103575; (2003); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 13466-38-1, The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 13466-38-1, name is 5-Bromopyridin-2-ol. This compound has unique chemical properties. The synthetic route is as follows.

A mixture of 5-bromopyridin-2-ol (1 g, 5.75 mmol), ClCF2COONa (0.876 g, 5.75 mmol), Cs2CO3 (2.81 g, 8.62 mmol) in DMF (20 mL) was heated at 100oC for 3h. LCMS indicated that the desired compound was formed.40 mL of water and 40 mL of EA were added to the reaction mixture. The organic phase was separated, washed with water(20 mL), brine(20 mL), dried over Na2SO4, filtered and concentrated under vacuum to give a residue, which was purified by silica gel chromatography (PE/EA=100/1) to give the title compound as a colorless oil (0.3g, 23.30%).

According to the analysis of related databases, 13466-38-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; EDGEWISE THERAPEUTICS, INC.; HUNT, Kevin; KOCH, Kevin; RUSSELL, Alan; SCHLACHTER, Stephen; WINSHIP, Paul; STEELE, Chris; UZOHO, Grace; (219 pag.)WO2020/97265; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 100367-39-3, name is 4-Bromo-2-methoxypyridine. This compound has unique chemical properties. The synthetic route is as follows. Product Details of 100367-39-3

General procedure: 5.1.12 2-[4-({[1-Methyl-4-(2-methylpyridin-4-yl)-1H-pyrazol-3-yl]oxy}methyl)phenyl]quinoline dihydrochloride (13a) Under argon gas atmosphere, to the mixture of 12 (200 mg, 0.45 mmol), 4-bromo-2-methylpyridine (156 mg, 0.91 mmol), and Na2CO3 (144 mg, 1.36 mmol) in DMF (2.0 mL) and water (0.87 mL) was added [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane complex (PdCl2(dppf)·CH2Cl2, 22 mg, 0.027 mmol), and the mixture was stirred at 100 C for 1 h. After cooling at room temperature, the mixture was concentrated in vacuo, and the residue was purified by silica gel column chromatography (0-5% MeOH in CHCl3) to give a free from of the title compound, which was dissolved in MeOH and the mixture was treated with 4 M HCl/EtOAc. The precipitate formed was collected by filtration and washed with Et2O to give 13a (91 mg, 42%) as a colorless solid. 5.1.14 2-[4-({[4-(2-Methoxypyridin-4-yl)-1-methyl-1H-pyrazol-3-yl]oxy}methyl)phenyl]quinoline dihydrochloride (13c) Compound 13c was prepared from 12 and 4-bromo-2-methoxylpyridine in a manner similar to that described for compound 13a, with a yield of 51% as a colorless solid. 1H NMR (DMSO-d6) delta 3.79 (s, 3H), 3.95 (s, 3H), 5.47 (s, 2H), 7.29 (s, 1H), 7.41 (dd, 1H, J = 5.9, 1.3 Hz), 7.71-7.76 (m, 3H), 7.89-7.95 (m, 1H), 8.13 (d, 1H, J = 8.2 Hz), 8.17 (d, 1H, J = 5.9 Hz), 8.28 (d, 2H, J = 8.7 Hz), 8.33 (d, 2H, J = 8.4 Hz), 8.45 (s, 1H), 8.72 (d, 1H, J = 8.6 Hz); MS (ESI) m/z 423 [M+H]+; Anal. Calcd for C26H22N4O2·2.2HCl·3.5H2O: C, 56.10; H, 5.58; N, 10.06; Cl, 12.74. Found: C, 56.33; H, 5.68; N, 9.88; Cl, 12.52.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, 100367-39-3, 4-Bromo-2-methoxypyridine.

Reference:
Article; Hamaguchi, Wataru; Masuda, Naoyuki; Miyamoto, Satoshi; Shiina, Yasuhiro; Kikuchi, Shigetoshi; Mihara, Takuma; Moriguchi, Hiroyuki; Fushiki, Hiroshi; Murakami, Yoshihiro; Amano, Yasushi; Honbou, Kazuya; Hattori, Kouji; Bioorganic and Medicinal Chemistry; vol. 23; 2; (2015); p. 297 – 313;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 13472-60-1, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 13472-60-1, name is 3,5-Dibromo-2-methoxypyridine, molecular formula is C6H5Br2NO, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Preparation 46-Bromo-2,2-dimethyl-2H-pyrano[2,3-b]pyridin-4(3H)-one[00153]A solution of 3,5-dibromo-2-methoxypyridine (1 1 .4 g, 42.7 mmol) in dry diethyl ether is cooled to -65 C and treated with BuLi (19 mL 2.5 M solution in hexane, 47.5 mmol) under argon atmosphere. The mixture is stirred at -70 C for 0.5 h. A solution of 3-methylbut-2-enal (3.44 g, 40.9 mmol) in dry THF (10 mL) is added to the mixture, and stirring is continued for another 0.5 h at -70 C. The reaction mixture is then warmed to r.t. and quenched with a saturated solution of sodium bicarbonate (100 mL). After extraction with DCM (3 x 100 mL) the combined organic layers are dried over Na2S04 and concentrated under reduced pressure to yield 1 -(5-bromo-2-methoxypyridin-3-yl)-3- methylbut-2-en-1 -ol (1 1 g, 95%).

According to the analysis of related databases, 13472-60-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERZ PHARMA GMBH & CO. KGAA; HENRICH, Markus; ABEL, Ulrich; MULLER, Sibylle; KUBAS, Holger; MEYER, Udo; HECHENBERGER, Mirko; KAUSS, Valerjans; ZEMRIBO, Ronalds; WO2012/52451; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem