Day: April 14, 2022

Electric Literature of 90145-48-5 ,Some common heterocyclic compound, 90145-48-5, molecular formula is C6H5BrN2O, 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.

a) tert-Butyl 2-(6-carbamoylpyridin-3-yl)-lH-indole-l-carboxylatel-(tert-butoxycarbonyl)indole-2-boronic acid (1 mmol), 5-bromopyridine-2-carboxamide (lmmol), Pd(dppf)Cl2 (0.05 mmol) and aq 2M Na2CO3 (1.5 mL) solution were mixed in THF/water 5:1 (10 mL) in a 20 mL microwave vial. The reaction mixture was stirred at 1200C in the microwave reactor for 15 min. Water was added and the solution was extracted with EtOAc. The organic extracts were dried over Na2SO4, filtered and concentrated. The crude mixture was purified by flash chromatography (Heptane/EtOAc gradient) to afford the title intermediate (172 mg). MS m/z (M+H) 338.

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. 90145-48-5, 5-Bromopyridine-2-carboxamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ASTRAZENECA AB; WO2008/108729; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 823221-93-8, 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.823221-93-8, name is 5-Bromo-2-chloro-4-(trifluoromethyl)pyridine, molecular formula is C6H2BrClF3N, molecular weight is 260.44, as common compound, the synthetic route is as follows.

Step C. (1 S, 1 aS,6aR)-4-((5-(6-chloro-4-(trifluoromethyl)pyridin-3-yl)-2-fluorobenzyl)oxy)- l, la,6,6a-tetrahvdrocyclopropara1indene-l -carboxylic acid, ethyl ester 5-Bromo-2-chloro-4-(trifluoromethyl)pyridine (974 mg, 3.74 mmol) was added to a solution of (l S,laS,6aR)-4-((2-fluoro-5-(4,4,5,5-tetramethyl- l,3,2-dioxaborolan-2- yl)benzyl)oxy)-l, la,6,6a-tetrahydrocyclopropa[a]indene-l -carboxylic acid, ethyl ester (1.583 g, 3.5 mmol) in DME (20 ml) under N2, followed by potassium carbonate (2.43 g, 17.58 mmol) and l,l’-bis(diphenylphosphino)ferrocene-palladium(ii)dichloride dichloromethane complex (35 mg, 0.043 mmol). The mixture was heated at 90C overnight. It was poured into saturated NH4CI solution and extracted with EtOAc (lx). The organic phase was washed with brine, dried (MgS04), filtered and the solvent evaporated. The residue was purified on silica gel using hexane and to give the title compound. MS m/e: (M+H)+ 506, 508.

The chemical industry reduces the impact on the environment during synthesis 823221-93-8, I believe this compound will play a more active role in future production and life.

Reference:
Patent; MERCK SHARP & DOHME CORP.; HAGMANN, William, K.; LI, Bing; SZEWCZYK, Jason, W.; WANG, Bowei; PARKER, Dann; BLIZZARD, Timothy; JOSIEN, Hubert; BIJU, Purakkattle; CHOBANIAN, Harry; GUDE, Candido; NARGUND, Ravi, P.; PIO, Barbara; DANG, Qun; LIN, Linus, S.; HU, Bin; CUI, Mingxiang; CHEN, Zhengxia; DAI, Meibi; ZHANG, Zaihong; LV, Ying; TIAN, Lili; WO2015/95256; (2015); 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 62150-47-4, name is Ethyl 4-bromopicolinate. This compound has unique chemical properties. The synthetic route is as follows. COA of Formula: C8H8BrNO2

To a stirring solution of compound 2.3 (32.4 g,. 0.14 mol). compound 2,4 (32.2 g, 0.17 mol) and Pd(PPh2)4 (8.08 g, 7 ram of) in 1 ,4-dioxane/nrietrianoi (800 rnL 1 :1) was added Na2COs (22.3 g,u.21 mol) under an argon atmosphere and the mixture was stirred at 80C for 15 nr. The solvent was removed under reduced pressure and the resulting residue was diluted with wafer (500 rnL) and extracted with EtOAc (3 x 500 ml). The combined organic layers were dried and concentrated under reduced pressure to give a crude, which was purified by flash chromatography (silica gel/ RhoEpsilon.Alpha 2: 1) to give ethyl 4-(4-formylphenyl picolinate (2.5, 14.2 g, 40%) as a yellow solid.

With the rapid development of chemical substances, we look forward to future research findings about 62150-47-4.

Reference:
Patent; ACHAOGEN, INC.; PATTERSON, Brian D.; LU, Qing; AGGEN, James Bradley; DOZZO, Paola; KASAR, Ramesh Annasaheb; LINSELL, Martin Sheringham; KANE, Timothy Robert; GLIEDT, Micah James; HILDEBRANDT, Darin James; MCENROE, Glenn A.; COHEN, Frederick; WO2013/170165; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 880870-13-3, name is 5-Bromo-2-chloro-4-methoxypyridine. A new synthetic method of this compound is introduced below., Application In Synthesis of 5-Bromo-2-chloro-4-methoxypyridine

A solution of 5-bromo-2-chloro-4-methoxypyridine (5.0 g, 22.48 mmol) in DMF (80 mL) was purged with nitrogen for 15 minutes. At this point, Zn(CN)2 (3.96 g, 33.7 mmol) and Pd(Ph3P)4 (2.60 g, 2.25 mmol) were added, successively. The resulting suspension was stirred at 95 C for 12 hours under nitrogen atmosphere. The reaction mixture was cooled to ambient temperature, and filtered to remove inorganic solid. The solvent (DMF) was evaporated to provide the crude residue as an oil, which was purified on silica gel and eluted with 0-30% ethyl acetate / hexanes to afford the product. 1H NMR (500 MHz, DMSO- , 5 8.69 (s, 1H), 7.50 (s, 1H), 4.04 (s, 3H); LC MS (M+l)+ – 169.

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, 880870-13-3, 5-Bromo-2-chloro-4-methoxypyridine.

Reference:
Patent; MERCK SHARP & DOHME CORP.; WALSH, Shawn, P.; PASTERNAK, Alexander; SHI, Zhi-Cai; CATO, Brian; KIM, Esther, Y.; WO2013/66718; (2013); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 62002-31-7, 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.62002-31-7, name is 4,5,6,7-Tetrahydro-3H-imidazo[4,5-c]pyridine dihydrochloride, molecular formula is C6H11Cl2N3, molecular weight is 196.08, as common compound, the synthetic route is as follows.

To a suspension of 3,3-diphenylpropionic acid (14 mg, 0.06 mmol) and HOBt (9 mg, 0.07 mmol) in ethyl acetate (1.5 mL) a solution of EDC (12 mg, 0.06 mmol) in ethyl acetate (0.5 mL) was added. The resulting mixture was shaken for 20 min at room temperature and then 4,5,6,7-tetrahydroimidazo[4,5-c]pyridine dihydrochloride (12 mg, 0.06 mmol) and triethylamine (0.02 mL) were added. After shaking for 16 h the mixture was washed with brine (2*2 mL), and the organic phase was concentrated. 12 mg (60%) of the title amide was obtained. HPLC (214 nm): elution at 8.71 min. LC-MS: Calcd. for MH+: 332; found: 332. 1H NMR (300 MHz, CDCl31 two rotamers, 1:1): delta2.55 (m, 2H), 3.15 (t, J=7 Hz, 2H), 3.61 (t, J=5 Hz, 1H), 3.80 (t, J=5 Hz, 1H), 4.41 (s, 1H), 4.57 (s, 1H), 4.67 (m, 1H), 7.06-7.30 (m, 10H), 7.39 (s, 0.5H), 7.43 (s, 0.5H).

The chemical industry reduces the impact on the environment during synthesis 62002-31-7, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Novo Nordisk A/S; US6908926; (2005); B1;,
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. 1440519-73-2, name is 2-Chloro-6-(4-methoxybenzyl)-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-5-one, molecular formula is C15H13ClN2O2, 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. SDS of cas: 1440519-73-2

To a solution of 2-chloro-6-(4-methoxy-benzyl)-6,7-dihydro-pyrrolo[3,4-b]pyridin-5-one (5.8 g, 20.0 mmol) in THF (50 mL) was added sodium hydride (60% in mineral oil, 1.7 g, 42.0 mmol) at room temperature. The resulting reaction mixture was stirred for 30 min before iodomethane (6.0 g, 42.0 mmol) was added. After stirring at room temperature over night, the mixture was quenched with water and extracted with EtOAc. The organic layer was then washed with brine, dried over anhy. Na2S04, filtered and concentrated in vacuo to give the crude product which was then purified by flash column chromatography (silica gel 20 g, 5% to 20% ethyl acetate in DCM). The title compound was obtained (3.8 g, 57%) as a white solid. MS: 316.2 (M+H+).

With the rapid development of chemical substances, we look forward to future research findings about 1440519-73-2.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; AEBI, Johannes; AMREIN, Kurt; CHEN, Wenming; HORNSPERGER, Benoit; KUHN, Bernd; LIU, Yongfu; MAERKI, Hans P.; MAYWEG, Alexander V.; MOHR, Peter; TAN, Xuefei; WANG, Zhanguo; ZHOU, Mingwei; WO2013/79452; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 16205-47-3, name is 7-Methylpyrazolo[1,5-a]pyridine-3-carboxylic acid. A new synthetic method of this compound is introduced below., SDS of cas: 16205-47-3

EXAMPLE 11 Synthesis of (R)-(+)-N-(1-azabicyclo[2.2.2]oct-3-yl)-7-methylpyrazolo[1,5-a]pyridine-3-carboxamide A solution of 166 mg (0.945 mmol) of 7-methyl-3-pyrazolo[1,5-a]pyridinecarboxylic acid in 3 ml of thionyl chloride was heated under reflux for 30 minutes. Thionyl chloride was distilled off under reduced pressure and the residue was dissolved in 5 ml of methylene chloride. The resultant solution was added dropwise under ice cooling to a solution of 200 mg (1 mmol) of (R)-(+)-1-azabicyclo[2.2.2]octan-3-amine, which had been prepared in accordance with the procedure disclosed in Japanese Patent Application Laid-Open No. 196583/1988, in 5 ml of methylene chloride.

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, 16205-47-3, 7-Methylpyrazolo[1,5-a]pyridine-3-carboxylic acid.

Reference:
Patent; Asahi Kasei Kogyo Kabushiki Kaisha; US5200415; (1993); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 139163-56-7, Adding some certain compound to certain chemical reactions, such as: 139163-56-7, name is 1-(6-Bromopyridin-2-yl)ethanol,molecular formula is C7H8BrNO, 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 139163-56-7.

Intermediate 17-1 Methyl 6-(1-hydroxyethyl)pyridine-2-carboxylate (1339) (1340) 2.00 g of 1-(6-bromopyridin-2-yl)ethanol (Telfer, Shane G.; Kuroda, Reiko, Chemistry A European Journal, 2005, 11, 57-68) were suspended in 20 ml of methanol and 30 ml of dimethyl sulphoxide. 265 mg of 1,3-bis(diphenylphoshino)propane, 140 mg of palladium(II) acetate and 3.2 ml of triethylamine were added, the mixture was flushed three times with carbon monoxide and stirred in a carbon monoxide atmosphere (12 bar 0.5 h, then at 16 bar overnight). Water was added, the mixture was extracted with ethyl acetate and the extract was concentrated. This gave 1.7 g of methyl 6-(1-hydroxyethyl)pyridine-2-carboxylate as an oil (crude product). (1341) 1H-NMR (400 MHz, CHLOROFORM-d): delta=1.57 (d, 3H), 4.02 (s, 3H), 5.03 (q, 1H), 7.56 (d, 1H), 7.88 (t, 1H), 8.05 (d, 1H).

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. 139163-56-7, 1-(6-Bromopyridin-2-yl)ethanol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Bayer Pharma Aktiengesellschaft; BOTHE, Ulrich; SIEBENEICHER, Holger; SCHMIDT, Nicole; ROTGERI, Andrea; BOeMER, Ulf; RING, Sven; IRLBACHER, Horst; GUeNTHER, Judith; STEUBER, Holger; LANGE, Martin; SCHAeFER, Martina; (191 pag.)US2016/311833; (2016); 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 863878-22-2, name is 6-Chloro-4-methyl-3-nitropyridin-2-amine. This compound has unique chemical properties. The synthetic route is as follows. Safety of 6-Chloro-4-methyl-3-nitropyridin-2-amine

Step A: 6-Chloro-4-methyl-3-nitropyridin-2-amine (187 mg, 1 mmol), iron powder (56 mg, 10 mmol) in AcOH (3 mL) was stirred at 100 C for 16 h. The mixture was concentrated. To the residue was added aqueous NaOH (2 N) until pH >9. The mixture was filtered through Celite. The filtrate was extracted with EtOAc (50 mL X 3). The organic layer was washed with brine, dried over Na2S04 and concentrated to afford 5-chloro-2,7-dimethyl-3H-imidazo[4,5-b]pyridine, which was used without further purification (154 mg crude, 85% crude). MS m/z 182.0, 184.0 [M+H]+.

With the rapid development of chemical substances, we look forward to future research findings about 863878-22-2.

Reference:
Patent; PTC THERAPEUTICS, INC.; WOLL, Matthew, G.; AMEDZO, Lukiana; BABU, Suresh; BARRAZA, Scott, J.; BHATTACHARYYA, Anuradha; KARP, Gary, Mitchell; MAZZOTTI, Anthony, R.; NARASIMHAN, Jana; PATEL, Jigar; TURPOFF, Anthony; XU, Zhenrong; (251 pag.)WO2018/226622; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 166266-19-9 , The common heterocyclic compound, 166266-19-9, name is 5-Iodo-3-methylpyridin-2-amine, molecular formula is C6H7IN2, 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.

Sodium nitrite (0.708 g, 10.25 mmol) was added to a mixture of 5-iodo-3-methyl-pyridin-2- ylamine (2 g, 8.55 mmol) and H2504 (12 mL) at 0 C. The reactiom mixture was stirred 15 mm at 60C, allowed to cool down, and poured onto crushed ice. Boric acid (1.057 g, 17.09 mmol) was added and the solution was quickly heated to 100 C. The reaction mixture was cooled down and neutralized with a saturated aq. NH4OH solution. The suspension was filtered toafford the crude title product (1.67 g, 7.11 mmol, 83% yield) as a brown solid. tR: 2.85 mm (H PLC 1); tR: 0.62 mm (LC-MS 2); ESl-MS: 236 [M+H] (LC-MS 2).

The synthetic route of 166266-19-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; BLANK, Jutta; BORDAS, Vincent; COTESTA, Simona; GUAGNANO, Vito; RUEEGER, Heinrich; VAUPEL, Andrea; WO2014/191896; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem