Tag: M.W:100-200

13472-85-0, 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. 13472-85-0, name is 5-Bromo-2-methoxypyridine. A new synthetic method of this compound is introduced below.

Step A: (5 -bromo-2-methoxyisonicotinaldehyde (39-1)To a solution of diispropylamine (63 g, 642 mmol) in anhydrous THF (500 ml) was added nBuLi (2.5 M, in hexane, 256 mL, 642 mmol) dropwise under a N2 atmosphere at -78 C, and the mixture was stirred for 30 mm. To the reaction mixture was added a solution of 5-bromo-2-methoxypyridine (100 g, 535 mmol) in 100 mL of THF. The reaction mixture was stirred at -78C for lh, and then DMF (50 ml, 642 mmol) was added. After stirring for 30 mm, the reaction mixture was quenched with water and extracted with EtOAc. The organic layer was washed with water and brine, and dried over Na2SO4. After filtration and concentration, the residue was purified by silica gel column chromatography (eluted with petroleum ether: ethyl acetate= 10:1) togive solid 39-1. MS(ESI) mle (M+Hj: 216.0/218.0.

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. 13472-85-0, 5-Bromo-2-methoxypyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK SHARP & DOHME CORP.; HAGMANN, William, K.; NARGUND, Ravi, P.; BLIZZARD, Timothy, A.; JOSIEN, Hubert; BIJU, Purakkattle; PLUMMER, Christopher, W.; DANG, Qun; LI, Bing; LIN, Linus, S.; CUI, Mingxiang; HU, Bin; HAO, Jinglai; CHEN, Zhengxia; WO2014/22528; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

55589-47-4, 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. 55589-47-4, name is 3-Methylpicolinaldehyde. This compound has unique chemical properties. The synthetic route is as follows.

To a microwave vial was added 4-[6-(2,4-dimethylpyrazol-3-yl)pyridazin-3-yl]oxy- l,2,3,3a,4,5,6,6a-octahydrocyclopenta[c]pyrrole hydrochloride (12 mg, 0.04 mmol) in DCM (0.5 mL) and THF (0.5 mL). Next, 3-methyl-2-pyridinecarboxaldehyde (20.5 mu^, 0.18 mmol) was added followed by sodium triacetoxyborohydride (39 mg, 0.18 mmol). The resulting suspension was stirred at ambient temperature for 18h then analyzed by LCMS. To the reaction was added saturated NaHCCb, and extracted with chloroform/IPA (4: 1). The organic solvents were concentrated, and the crude product was dissolved in DMSO (1 mL) and purified using the Gilson (Acidic, 30 x 50 mm column, 15 – 60percent ACN/ 0.1percent aqueous TFA, 4 min run). Fractions containing the product were basified with saturated NaHCC and extracted with chloroform/IPA (4: 1). The solvents were concentrated to give the title compound (8.1 mg, 0.020 mmol, 55percent yield, 5: 1 dr) as a clear oil. LCMS (90 sec method): RT = 0.598, m/z = 405.2 [M + H]+. Major Product NMR (400 MHz, chloroform-^: delta 8.33 – 8.34 (m, 1H), 7.45 (d, J = 9.10 Hz, 1H), 7.42 – 7.44 (m, 1H), 7.39 (s, 1H), 7.07 – 7.11 (m, 1H), 6.98 (d, J = 9.10, 1H), 5.55 – 5.61 (m, 1H), 4.02 (s, 3H), 3.71 (s, 2H), 3.09 – 3.15 (m, 1H), 2.76 – 2.86 (m, 1H), 2.64 – 2.71 (m, 2H), 2.48 – 2.52 (m, 1H), 2.44 (s, 3H), 2.30 – 2.35 (m, 1H), 2.13 (s, 3H), 1.97 – 2.10 (m, 2H), 1.71 – 1.80 (m, 1H), 1.53 – 1.57 (m, 1H).

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, 55589-47-4, 3-Methylpicolinaldehyde.

Reference:
Patent; VANDERBILT UNIVERSITY; LINDSLEY, Craig W.; CONN, P. Jeffrey; ENGERS, Darren W.; TEMPLE, Kayla J.; (87 pag.)WO2019/89676; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

823-56-3, Adding a certain compound to certain chemical reactions, such as: 823-56-3, 2-Fluoro-3,5-dichloropyridine, 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, 823-56-3, blongs to pyridine-derivatives compound.

To a mixture of methyl (lr, 4r) -4-hydroxy-2′ -oxo-1′ , 2′ – dihydrospiro [cyclohexane-1, 3′ -indole] -5′ -carboxylate (1.00 g) and tetrahydrofuran (60 ml) was added sodium hydride (60% in oil, 436 mg) at 0C, and the mixture was stirred at the same temperature for 30 min and 3, 5-dichloro-2-fluoropyridine (723 mg) was added. After stirring at room temperature for 8 hr, N, -dimethylformamide (60 ml) was added, and the mixture was further stirred at room temperature for 12 hr. The reaction mixture was poured into ice-cooled water and extracted with ethyl acetate. The organic layer was separated, washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/petroleum ether) to give a white solid. To a mixture of the obtained solid, tetrahydrofuran (20 ml) and water (20 ml) was added lithium hydroxide monphydrate (130 mg) at room temperature, and the mixture was stirred at 50C for 3 hr and concentrated under reduced pressure. The residue was adjusted to pH=3.0 by adding 3N hydrochloric acid and extracted with ethyl acetate. The organic layer was separated, washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/petroleum ether) to give the title compound (1.00 g)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,823-56-3, its application will become more common.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; TERAO, Yoshito; TAKAHASHI, Masashi; HARA, Ryoma; HIDAKA, Kousuke; FURUKAWA, Hodeki; YAMASAKI, Takeski; KASAI, Shizuo; (147 pag.)WO2018/182051; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 16063-70-0 as follows., 16063-70-0

767 mg of ethyl 2-cyanopropionate and then 833 mg of potassium carbonate were added to a solution of 500 mg of 2,3,5-trichloropyridine in 5 ml of dimethyl sulfoxide.The reaction was stirred at 100 C. for 5 hours.After completion of the reaction, the reaction solution was cooled to room temperature, 10 ml of water was added, and the mixture was partitioned with 20 ml of ethyl acetate.The obtained organic layer is concentrated under reduced pressure, and the obtained residue is purified by silica gel chromatography (ethyl acetate: hexane = 1: 2)Thus, 270 mg of the desired product was obtained as a colorless oil (yield 49%).

The chemical industry reduces the impact on the environment during synthesis 16063-70-0, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Nissan Chemical Industries, Ltd.; Nakayama, Yosuke; Saito, Fumiyo; Nanju, Yusuke; (53 pag.)JP2019/34892; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

74115-13-2, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 74115-13-2, name is 5-Bromo-3-pyridinol, the common compound, a new synthetic route is introduced below.

Step 2: Synthesis of 3-bromo-5-(2-fluoroethoxy)pyridine A solution of 1.0 g (5.75 mmol) 3-bromo-5-hydroxypyridine, 1.85 g (13.2 mmol) K2CO3, and 2.25 g (10.3 mmol) 2-fluoroethyl tosylate in 14 mL DMF was heated overnight at 60C. After cooling to room temperature the solvent was stripped on the oil pump, and the residue was taken up in 100 mL water and extracted three times each with 50 mL chloroform. After stripping the solvent the crude product was obtained, which was purified by column chromatography: 1: 500 mL CH2Cl2 2: CH2Cl2/CH3OH 98/2 1.04 g (4.73 mmol, 82.2% yield) of a yellow liquid was obtained. Product characteristics: Thin-layer chromatography (silica gel): Rf 3-bromo-5-hydroxypyridine (CH2Cl2) = 0.05 Rf 3-bromo-5-(2-fluoroethoxy)pyridine (CH2Cl2) = 0.25 1H-NMR (CDCl3): delta = 8.28 (d, 1H), 8.22 (d, 1H), 7.30 (t, 1H), 4.75 (t, 1H), 4.60 (t, 1H), 4.28 (t, 1H), 4.17 (t, 1H)

Statistics shows that 74115-13-2 is playing an increasingly important role. we look forward to future research findings about 5-Bromo-3-pyridinol.

Reference:
Patent; Julius-Maximilians-Universitaet Wuerzburg; EP2394668; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

13472-85-0, 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.13472-85-0, name is 5-Bromo-2-methoxypyridine, molecular formula is C6H6BrNO, molecular weight is 188.02, as common compound, the synthetic route is as follows.

To a solution of diisopropylamine (22.7 g, 0.22 mol) in THF (0.5L) was cooled to -30C, and then added n-BuLi (140 mL, 0.22 mol). After addition, the resulting solution was stirred for 0.5 h. The mixture was cooled to -60 C, Example 60a (35.1 g,0.19 mol) dissolved in THF (200 mL) was added dropwise,maintained the temperature below -60 C, the resulting solution was stirred for 1 h. DMF (20.4 g 0.28 mol) was added dropwise at -60 C, the resulting solution was stirred for 1 h .The reaction mixture was quenched by saturated NH4C1 (200 mL) aqueous, and allowed warmed to room temperature .the residue was extracted with EtOAc (200 mL * 2). The combined organic phase was washed with brine, dried over Na2S04, filtrated and concentrated under reduced pressure to give the crude product which was further purified by silica gel chromatography to give the pure product (Example 60b, 26.4 g, yield 64.3%) as a white solid. i NMR ^OO MHz, CDC13) delta 10.28 (s, 1H), 8.40 (s, 1H), 7.16 (s, 1H), 3.95 (s, 3H)

Statistics shows that 13472-85-0 is playing an increasingly important role. we look forward to future research findings about 5-Bromo-2-methoxypyridine.

Reference:
Patent; FRONTHERA U.S. PHARMACEUTICALS LLC; JIN, Bohan; DONG, Qing; HUNG, Gene; (212 pag.)WO2017/218960; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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 271-63-6, name is 1H-Pyrrolo[2,3-b]pyridine. This compound has unique chemical properties. The synthetic route is as follows. 271-63-6

General procedure: A solution of indole, azaindole or pyrrole (0.1 mmol) in dichloromethane (5 mL) was added to a suspension of 1:1 (W/W) ICl (concentration indicated in the Table; 0.1 mmol = 162 mg) and Celite (162 mg) ratio in dichloromethane (10 mL). The mixture was stirred at room temperature for the time indicated in Tables 1-4. The reaction mixture was then poured into saturated thiosulfate solution (20 mL) extracted with dichloromethane (2 x 15 mL). The organic layer was washed in brine and, dried over sodium sulfate and the solvent was removed at reduced pressure. The desired compound was purified by chromatography column using hexane and ethyl acetate mixtures as eluting solvent. Yields of iodinated compounds are summarized in Tables 1-4. All the compounds were characterized by IR, NMR and were compared with authentic samples.

Statistics shows that 271-63-6 is playing an increasingly important role. we look forward to future research findings about 1H-Pyrrolo[2,3-b]pyridine.

Reference:
Article; Hamri, Salha; Rodriguez, Jose; Basset, Joan; Guillaumet, Gerald; Dolors Pujol; Tetrahedron; vol. 68; 31; (2012); p. 6269 – 6275;,
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. 609-71-2, name is 2-Oxo-1,2-dihydropyridine-3-carboxylic acid. This compound has unique chemical properties. The synthetic route is as follows. 609-71-2

This compound was synthesized by a method similar to the method described in . To a 50-mL round bottom flask, 2-oxo-1,2-dihydropyridine-3-carboxylic acid (500 mg, 3.59 mmol) was added, and suspended in methanol (5 mL) and water (0.8 mL), then potassium hydroxide (400 mg, 7.13 mmol) was added to the suspension, and the resulting mixture was stirred at 100C for 15 minutes. The reaction solution was returned to room temperature, iodomethane (2.6 mL, 41.8 mmol) was added to the reaction solution, and the resulting mixture was stirred at 100C for 45 minutes, and then concentrated under reduced pressure until the solvent volume was reduced by half. To the reaction solution, 3 N hydrochloric acid (20 mL) was added, and the produced solid was collected by filtration, washed with water and acetonitrile, and then dried under reduced pressure to obtain the title compound (64.9 mg, 12%) as white powder. 1H NMR(CD3 OD, 400 MHz): 8 8.43 (dd, 1H, J = 6.9, 2.3 Hz), 8.05 (dd, 1H, J = 6.9, 2.3 Hz), 6.65 (t, 1H, J = 6.9 Hz), 3.70 (s, 3H)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,609-71-2, 2-Oxo-1,2-dihydropyridine-3-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; Nippon Chemiphar Co., Ltd.; NAGASE, Hiroshi; FUJII, Hideaki; SAITOH, Akiyoshi; NAKATA, Eriko; HIROSE, Masaaki; OOI, Isao; HAYASHIDA, Kohei; (88 pag.)EP3513792; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding some certain compound to certain chemical reactions, such as: 53939-30-3, name is 5-Bromo-2-chloropyridine, 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 53939-30-3. 53939-30-3

2-chloro-5-bromopyridine (4.0 mmol) was added to CHC13 (40 mL), stirred under nitrogen, and BPO (0.08 mmol) and NBS (4.4 mmol) were added to the mixture. The reaction was heated to reflux for 5 h and cooled.The solvent was distilled off under reduced pressure to give a crude product.A solution of morpholine (0.50 mol) in ethanol was added to the crude product of the previous step under nitrogen and stirred at room temperature overnight.The solvent was removed under reduced pressure.The crude product was purified by column chromatography to give 4-(4-bromo-2-fluorophenyl)morpholine.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 53939-30-3.

Reference:
Patent; Ocean University of China; Shao Changlun; (69 pag.)CN108658937; (2018); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

100-26-5, 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 100-26-5, name is 2,5-Pyridinedicarboxylic acid. This compound has unique chemical properties. The synthetic route is as follows.

To a round bottom flask connected with condenser, pyridine-2, 5- dicarboxylic acid (20 mmol, 3.34 g), SOCI2 (60 mmol, 7.14 g) and 5 ml_ of DMF were added and the reaction was carried out at 90C under argon for 4 h. The reaction mixture was then cooled down to room temperature, Et3N (6 equiv. , 1 6.8 ml_) and glycerol carbonate (80 mmol, 9.45 g in 1 2 mL of THF) were added slowly and was further heated at 90C overnight. After the reaction, the excess amount of Et3N, SOCI2 and solvent were removed under vacuum. The product bis((2-oxo-1 ,3-dioxolan-4-yl)methyl)pyridine-2,5- dicarboxylate was isolated as a white solid, filtered and washed with water (30 mL, 2 times) and with Et20 (30 mL, 2 times) to give 4.61 g (1 2.6 mmol) of pure product (63%) which was characterized by 1 H, 13C-NMR and HRMS. 1 H- NMR (CDCb, 400 MHz) : 9.1 9 (dd, J = 2.1 , 0.8 Hz, 1 H), 8.49 (dd, J = 8.2, 2.2 Hz, 1 H), 8.21 (dd, J = 8.1 , 0.8 Hz, 1 H), 5.36 – 5.05 (m, 2H), 4.84 – 4.31 (m, 8H). 13C NMR (CDCb, 100 MHz): d= 168.8, 168.6, 159.9, 159.8, 1 55.5, 1 55.4, 143.8, 1 33.2, 1 30.3, 79.4, 79.3, 71 .4, 71 .3, 70.2, 70.1 . HR-MS (ESI) (M+H)+ m/z Calcd. for CisHuNOio: 368.061 2. Found: 368.061 0.

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 100-26-5, 2,5-Pyridinedicarboxylic acid.

Reference:
Patent; AGENCY FOR SCIENCE, TECHNOLOGY AND RESEARCH; SEAYAD, Jayasree; JANA, Satyasankar; SEAYAD, Abdul Majeed; (115 pag.)WO2019/190409; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem