Day: April 12, 2022

Electric Literature of 65169-42-8 , The common heterocyclic compound, 65169-42-8, name is Methyl 6-chloro-5-methylnicotinate, molecular formula is C8H8ClNO2, 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.

Preparation 3; 5-Formyl-3-methyl-2-pyridinecarbonitrile (Used to prepare Example 32) (a) (6-Chloro-5-methyl-3-pyridinyl)methanolTo a solution of methyl 6-chloro-5-methyl-3-pyridinecarboxylate (84 mg, 0.453 mmol) in DCM (2 ml), DIBAL-H (1.5 M solution in toluene, 0.905 ml, 1.358 mmol) was added dropwise under N2 at -78 C. The reaction mixture was allowed to attain rt and stirred overnight. After 18 h, TLC showed no starting material. The reaction was quenched by addition of sodium-potassium tartrate saturated solution, extracted with DCM, dried, filtered, and concentrated to afford (6-chloro-5-methyl-3-pyridinyl)methanol (63 mg, 0.400 mmol, 88% yield) pure enough to be used in the next step.1H-NMR (delta ppm, CDCl3): 8.17 (s, 1H), 7.60 (s, 1H), 4.69 (s, 2H), 2.37 (s, 3H).

The synthetic route of 65169-42-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Alemparte-Gallardo, Carlos; Barfoot, Christopher; Barros-Aguirre, David; Cacho-Izquierdo, Monica; Fiandor Roman, Jose Maria; Hennessy, Alan Joseph; Pearson, Neil David; Remuinan-Blanco, Modesto Jesus; US2009/306089; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 915006-52-9, 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. 915006-52-9, name is 6-Bromo-2-iodopyridin-3-amine, molecular formula is C5H4BrIN2, 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.

To a mixture of 6-bromo-2-iodopyridin-3-amine (100 mg, 0.34 mmol), 1,2-dimethoxy-4-(prop-1-yn-1-yl)benzene (74 mg, 0.42 mmol), lithium chloride (18 mg, 0.42 mmol), sodium carbonate (180 mg, 1.68 mmol) and Pd(dppf)Cl2 (12.5 mg, 0.017 mmol) in a screw cap vial was added DMF (2 mL). The vial was fitted with a Teflon-lined septum cap. The system was evacuated under vacuum (via a needle from a nitrogen/vacuum manifold line) and backfilled with nitrogen gas. The procedure was repeated three times. The needle was removed and the vial was heated at 100 C. for 16 h. LCMS analysis shows formation of two isomers, in approximately 3:1 ratio. 1H NMR analysis suggested the major product to be 5-bromo-2-(3,4-dimethoxyphenyl)-3-methyl-1H-pyrrolo[3,2-b]pyridine (5A-1). The reaction mixture was diluted with EtOAc (50 mL), poured into a separatory funnel and washed with 10% aqueous LiCl solution (2*10 mL) and saturated aqueous NaCl solution (10 mL), dried (Na2SO4), filtered and the filtrate was concentrated. The crude product was dissolved in a small amount of DCM and purified on a silica gel column chromatography with a 15 min gradient from 0%-100% DCM/EtOAc to afford 5-bromo-2-(3,4-dimethoxyphenyl)-3-methyl-1H-pyrrolo[3,2-b]pyridine (Intermediate 5A-1) that was contaminated with Intermediate 5A-2, 5-bromo-3-(3,4-dimethoxyphenyl)-2-methyl-1H-pyrrolo[3,2-b]pyridine, m/z (303, M+1), 80 mg (67%).

According to the analysis of related databases, 915006-52-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; Dyckman, Alaric J.; Dodd, Dharmpal S.; Mussari, Christopher P.; Sherwood, Trevor C.; Whiteley, Brian K.; Gilmore, John L.; Kumar, Sreekantha Ratna; Pasunoori, Laxman; Srinivas, Pitani Veera Venkata; Duraisamy, Srinivasan Kunchithapatham; Hegde, Subramanya; Anumula, Rushith Kumar; US2019/185469; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 956010-87-0, 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 956010-87-0 as follows.

To compound 12 (100 mg, 0.53 mmol) and morpholine (93 mg, 1.07 mmol) was added a 1N aqueous sodium hydroxide solution (2.0 mL), and the mixture was heated in a microwave oven to 150 C for 10 min. The mixture was extracted with ethyl acetate, neutralized with 4N HCl solution and again extracted. The combined organic layers were dried over sodium sulfate, and the solvent was evaporated to yield 117mg (95 %) of the title compound. 1H NMR (400 MHz, DMSO-d6): delta 3.63-3.75 (m, 6H), 4.07-4.15 (m, 2H), 7.32 (dd, J=8.1, 4.5Hz, 1H), 8.42 (dd, J=8.1, 1.5Hz, 1H), 8.60 (dd, J=4.5, 1.5Hz, 1H), 14.15 (br s, 1H). 13C NMR (125 MHz, DMSO-d6): delta 42.3, 46.9, 66.1, 66.4, 114.8, 118.2, 131.1, 138.1, 149.5, 151.6, 161.0. HRMS m/z calcd for C11H12N4O2: 232.0960; found: 232.0962.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,956010-87-0, its application will become more common.

Reference:
Article; Schirok, Hartmut; Griebenow, Nils; Fuerstner, Chantal; Dilmac, Alicia M.; Tetrahedron; vol. 71; 34; (2015); p. 5597 – 5601;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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.89640-55-1, name is 3-Iodo-4-methoxypyridine, molecular formula is C6H6INO, molecular weight is 235.02, as common compound, the synthetic route is as follows.HPLC of Formula: C6H6INO

Preparation 94 To a suspension of 3-iodo-4-methoxypyridine (0.62g), 3-nitrophenylboronic acid (0.57g) and tetrakis(triphenylphosphine)palladium(0) (152mg) in dimetoxyethane (10ml) was added aqueous sodium carbonate (2M, 3.43ml) and the mixture was stirred at 60C for 6 hours. The mixture was diluted with ethyl acetate and washed with aqueous sodium hydroxide (1N) and brine. The separated organic layer was dried over magnesium sulfate and evaporated. The residue was purified with silica gel (25g) column chromatography and eluted with 40-80% ethyl acetate in n-hexane to give 3-(4-methoxypyridin-3-yl)nitrobenzene (84mg). APCI-mass;m/z231(M+H+) 1H-NMR(DMSO-d6): delta;3.90(3H,s), 7.24(1H,d,J=5.8Hz), 7.75(1H,t,J=8.0Hz), 8.00 (1H,d,J=8.0Hz), 8.24(1H,dt,J=8.2Hz,1.1Hz), 8.35(1H,t,J=1.0Hz), 8.48(1H,s), 8.53(1H, d,J=7.6Hz)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,89640-55-1, 3-Iodo-4-methoxypyridine, and friends who are interested can also refer to it.

Reference:
Patent; FUJISAWA PHARMACEUTICAL CO., LTD.; EP1264820; (2002); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 3796-24-5, Adding some certain compound to certain chemical reactions, such as: 3796-24-5, name is 4-(Trifluoromethyl)pyridine,molecular formula is C6H4F3N, 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 3796-24-5.

Reagents and conditions: (i) mCPBA, EtOAc; (ii) POCl3; (iii) PdPPh3) 2C12, Ba(OH)2, DME-H2O, 110 0C; (iv) 5-fluoro-lH- pyrazolo [3, 4-b] pyridin-3-amine, Pd(OAc)2, Xantphos, K2CO3, dioxane, 120 0C.[0054] Scheme III above shows a general synthetic route that is used for preparing the compounds III-5. Compounds of formula III-5 can be prepared from intermediate III-l. The formation of chloropyridine derivative III-2 is achieved by treating the corresponding pyridine III-l with m-CPBA in EtOAc followed by conversion of the corresponding N-oxide to the chloropyridine by treating it with POCl3. Intermediate III-2 is then reacted with the corresponding boronic acid derivative to yield compound III- 3 using Suzuki coupling conditions well known for those skilled in the art. This reaction is amenable to a variety of boronic acid derivatives. The pyridine III-3 is then converted in a chloropyridine derivative III-4 using the same two step procedures as used in step 1, m-CPBA oxidation followed by POCl3 treatment. Intermediate III-4 is then treated with 5-fluoro-lH- pyrazolo [3, 4-b] pyridin-3-amine in the presence of Pd as a catalyst to yield the final compound III-5.

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. 3796-24-5, 4-(Trifluoromethyl)pyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; WO2009/18415; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 89415-54-3, 5-Bromo-N2-methylpyridine-2,3-diamine, 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, name: 5-Bromo-N2-methylpyridine-2,3-diamine, blongs to pyridine-derivatives compound. name: 5-Bromo-N2-methylpyridine-2,3-diamine

To a solution of 5-bromo-N2-methylpyridine-2,3-diamine (14 g, 69 mmol) in DMF (702 mL) at room temperature was added CDI (29 g, 180 mmol). The reaction mixture was stirred for 16 h. LCMS analysis of the crude reaction mixture showed that the reaction was not complete, and the resultant residue was re-dissolved in THF and CDI (11.2, 69 mmol) was added. The reaction mixture was stirred at 60 C for 16 h. The reaction mixture was quenched with water and diluted with Et2O. The suspension was filtered and the resulting solid was washed with Et2O and dried under vacuum to yield the title compound as a black solid (15.8 g, 35.7 mmol), which was used in the next step without further purification. MS (ESI): mass calcd. for C7H6BrN3O, 226.97; m/z found, 227.0 [M+H]+.

The synthetic route of 89415-54-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; CHROVIAN, Christa C.; LETAVIC, Michael A.; RECH, Jason C.; RUDOLPH, Dale A.; JOHNSON, Akinola Soyode; STENNE, Brice M.; WALL, Jessica L.; (533 pag.)WO2018/67786; (2018); 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. 61494-55-1, name is 2-(2-Chloropyridin-3-yl)acetic acid. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 2-(2-Chloropyridin-3-yl)acetic acid

INTERMEDIATE 13; r2-Chloropyridin-3-yl)acetic acid methyl ester; To a suspension of Intermediate 12 (3.88 g, 22.6 mmol) in methanol was added acetyl chloride (1.8 mL, 24.9 mmol) and the mixture heated at 700C for 18 hours. The solvents were removed in vacuo to give the title compound as a pale brown oil (4.63 g, quant). deltaH (DMSOd6) 8.35 (IH, dd, J4.7, 1.9 Hz), 7.88 (IH, dd, J 8.5, 1.9 Hz), 7.43 (IH, dd, J8.5, 4.7 Hz), 3.80 (2H, s), 3.65 (3H, s). LCMS (ES+) RT 2.40 minutes, 186 (M+H)+.

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, 61494-55-1, 2-(2-Chloropyridin-3-yl)acetic acid.

Reference:
Patent; UCB PHARMA S.A.; WO2007/88345; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 884494-51-3 ,Some common heterocyclic compound, 884494-51-3, molecular formula is C6H3FINO2, 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 suspension of 2-fluoro-4-iodonicotinic acid (896 mg, 3356 mumol) in 6M hydrochloric acid (13423 mul, 80540 mumol) was heated at 100 0C. After 5 min, the reaction became a solution, and then a precipitate appeared. The reaction mixture was stirred 60 min at 100 0C and then cooled to room temperature. Filtration afforded 2- hydroxy-4-iodonicotinic acid (710 mg, 2679 mumol, 80% yield). MS (ESI pos. ion) m/z: 248(M+H-H2O). Calc’d exact mass for C6H4INO3: 265.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,884494-51-3, its application will become more common.

Reference:
Patent; Amgen Inc.; WO2006/116713; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 21427-61-2, 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 21427-61-2, name is 5-Chloro-2-hydroxy-3-nitropyridine. This compound has unique chemical properties. The synthetic route is as follows.

(Reference Example 8-1) To an 80% aqueous ethanol suspension (150 ml) of 5-chloro-3-nitropyridin-2-ol (15.0 g) and calcium chloride (9.54 g) was added iron powder (24.0 g), followed by stirring at room temperature for 30 minutes, and further under heating at reflux for 1 hour. After the temperature was brought back to room temperature, the reaction suspension was filtered through Celite. Water was added to the filtrate, and extracted 8 times with a methanol-dichloromethane (1:10) mixed solvent. The collected organic layer was dried over anhydrous sodium sulfate, and concentrated under reduced pressure to afford 3-amino-5-chloropyridin-2-ol (8.86 g). 1H NMR (400 MHz, DMSO-D6) delta: 5.43 (s, 2H), 6.38 (d, 1H, J = 2.7 Hz), 6.72 (d, 1H, J = 2.7 Hz), 11.52 (s, 1H).

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 21427-61-2, 5-Chloro-2-hydroxy-3-nitropyridine.

Reference:
Patent; Daiichi Sankyo Company, Limited; EP2471792; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 2859-68-9, Adding some certain compound to certain chemical reactions, such as: 2859-68-9, name is 3-(Pyridin-2-yl)propan-1-ol,molecular formula is C8H11NO, 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 2859-68-9.

3-(2-Pyridyl)-propionic Acid In a 50 mL round-bottomed flask equipped with a stirring bar was placed 3-(2-pyridyl)-propanol (1 g, 7.6 mmol), water (13 mL) and concentrated sulfuric acid (0.5 9, 5.1 mmol). To this stirred solution was added over a period of 30 min potassium permanganate (1.8 g, 11.3 mmol) while the reaction temperature was maintained at 50 C. After the addition was completed, the mixture was held at 50 C. until the color of the reaction mixture turned brown, then heated at 80 C. for 1 hour and filtered. The filtrate was evaporated to dryness to yield quantitatively the desired acid (1.14 g) suitable for next step without further purification. To prepare a pure acid, the residue thus obtained was boiled in ethanol (10 mL) in the presence of charcoal (0.1 g) for 5 min, filtered and cooled to give crystalline 3- (2-pyridyl)-propionic acid (0.88 g, 78%).

According to the analysis of related databases, 2859-68-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Abbott Laboratories; US6162927; (2000); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem