Month: April 2022

Application of 946002-90-0, 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.946002-90-0, name is (S)-1-(5-Bromopyridin-2-yl)pyrrolidin-3-ol, molecular formula is C9H11BrN2O, molecular weight is 243.1, as common compound, the synthetic route is as follows.

(R)-5-Bromo-2-[3-(2,6-dichloro-4-methyl-phenoxy)-pyrrolidin-l-yl]-pyridine. ADDP (11.7 g, 45.4 mmol) was added to a sol. of compound Gl (8.82 g, 36.3 mmol) and 2,6-dichloro-/?-cresol (7.37 g, 40.0 mmol) in toluene (200 mL). The mixture was degassed with nitrogen for 5 min, and PBu3 (85%, 15.8 mL, 46.2 mmol) was added. The mixture was heated rapidly to 100 0C, and stirred at this temperature for 2 h. The mixture was allowed to cool to rt, and was diluted with heptane (200 mL). The mixture was filtered, and the filtrate was evaporated under reduced pressure. Purification of the residue by FC (EtO Ac/heptane 1 :7) yielded a crude title compound that was diluted with CH2Cl2. This mixture was washed with aq. IM NaOH. The org. layer was dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Drying the residue under high vacuum yielded the pure title compound (13.5 g, 93%). LC-MS: tR = 0.92 min; ES+: 402.98.

The chemical industry reduces the impact on the environment during synthesis 946002-90-0, I believe this compound will play a more active role in future production and life.

Reference:
Patent; ACTELION PHARMACEUTICALS LTD; WO2007/88514; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 896722-51-3, name is 6-Methyl-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine, the common compound, a new synthetic route is introduced below. HPLC of Formula: C14H12N2O2S

A solution of 50% NaOH (0.573 g) was added to N-protected 6-methyl-7-azaindole (0.390 g, 1.43 mmol) in Ethanol (10 mL). After refluxed for 8 h, the mixture was concentrated and was extracted with CHCl3. The organic layer was washed with water and dried. The solvent was evaporated in vacuo and the residue was purified on a silica gel column eluting with EtOAc/hexane (1:3) to give 6-methyl-1H-pyrrolo[2,3-b]pyridine (0.148 g, 78%).

The synthetic route of 896722-51-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hsieh, Hsing-Pang; Chao, Yu-Sheng; Liou, Jing-Ping; Chang, Jang-Yang; Tung, Yen-Shih; US2006/148801; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 179687-79-7, Adding some certain compound to certain chemical reactions, such as: 179687-79-7, name is 2-((2-Chloro-4-nitrophenoxy)methyl)pyridine,molecular formula is C12H9ClN2O3, 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 179687-79-7.

Preparation of 3-chloro-4-(2-pyridylmethoxy)aniline from the nitrobenzene product of Example 1 was accomplished with catalytic hydrogenation using platinum on carbon. A typical hydrogenation was done using 6 volumes of THF, 2% by weight of 5% Pt/C (50% water wet), at 25 psi and at 25-30 C. for approximately 4-6 hours. The reaction is slightly exothermic and the temperature will rise to about 30-35 C. Cooling is necessary to maintain the temperature below 30 C. As a specific example, a mixture of 3-chloro-4-(2-pyridylmethoxy)nitrobenzene (0.15 kg, 0.57 mole) and 2% (w/w) of 5% Pt/C (6.0 g) in tetrahydrofuran (0.90 L) was hydrogenated at 25 psi for at least 5 hours. The mixture was filtered through a celite pad and washed with tetrahydrofuran (0.60 L). The filtrate was distilled to a volume of about 0.75 L and ethanol (1.12 L) was added. Distillation was continued to a volume of about 0.75 L and ethanol (2.85 L) was added. The mixture may be used ?as is? in the step of Example 3 below. ; Performing the hydrogenation in isopropyl alcohol (IPA), methanol (MeOH), or ethanol (EtOH) may result in the product being contaminated with late eluting impurity that partially precipitates out on standing in solution. It was found that performing the hydrogenation in a solvent where both the product and starting material are soluble, such as tetrahydrofuran (THF), resulted in greater product purity and required much less solvent. Thus, THF is a preferred solvent for this step. Experimental results showing the effect of different reaction conditions are shown in Table 2. For the larger scale runs, the first aniline intermediate was not isolated (?NI?) before proceeding with the next step. TABLE 2 Hydrogenation to Form First Aniline Intermediate 5% Scale (g) Pt/C** Solvent Vol Time (h) Yield (%) 2.0 1 IPA 50 3 79.6 18 2.0 5 EtOH 60 3100* 10 1 THF 10 4 94.5 7 10 1 EtOH 10 3 95.6 30 1.05 THF 6.5 12 96.3 14 100 2 THF 6 4.5 97.1 400 2 THF 6 4 NI 500 2 THF 6 4 NI 100 2 THF 6 5 NI 150 2 THF 6 5 NI 7 *Solid impurities noted after reaction completion. **percent by weight of starting material.

According to the analysis of related databases, 179687-79-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; WYETH; US2006/270668; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1201676-03-0, 4,6-Dichloro-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-1-one, 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, Application In Synthesis of 4,6-Dichloro-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-1-one, blongs to pyridine-derivatives compound. Application In Synthesis of 4,6-Dichloro-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-1-one

A mixture of 4,6-dichloro-2,3-dihydro-pyrrolo[3,4-c]pyridin-1-one (1.19 g, 5.87 mmol), triethylamine (2.97 g, 29.3 mmol), and crude trifluoroacetic acid salt of piperidine-4- carboxylic acid isobutyl amide [obtained by stirring 4-isobutylcarbamoyl-piperidine-1- carboxylic acid te/f-butyl ester (2.63 g, 8.80 mmol) in dichloromethane (20 mL) and trifluoroacetic acid (6 mL) for 1.5 hours, then removing solvents by rotary evaporation] in dioxane (10 mL) is heated in a 75 mL sealed tube at 120 0C for 68 h. Filtration of room temperature mixture does not lead to separation of regioisomers. The filtrate is concentrated down to dryness by rotary evaporation, dissolved into ethyl acetate, and then washed with water and brine. The organic layer is dried over sodium sulfate, filtered and concentrated down to dryness by rotary evaporation. This residue is then combined with solids from first filtration and eluted through a silica gel column (80:20 ethyl acetate / heptane, then 100% ethyl acetate, then 95:5 ethyl acetate / methanol). The more polar regioisomer (TLC solvents: 90:10 ethyl acetate / methanol) is concentrated down to dryness by rotary evaporation, then treated with a small amount of methanol. The pink solid is isolated by filtration (0.647 g, 1.84 mmol, 31 %). MS(ESI) m/z 351.20 (M+1 ). 1H NMR (400 MHz, DMSOd6) delta ppm 9.00 (s, 1 H), 7.79 (t, J=5.81 Hz, 1 H), 6.84 (s, 1 H), 4.54 (s, 2 H), 4.19 (d, J=13.39 Hz, 2 H), 3.09 – 2.92 (m, 2 H), 2.86 (dd, J=6.57, 6.06 Hz, 2 H), 2.48 – 2.36 (m, 1 H), 1.79 – 1.71 (m, 2 H), 1.71 – 1.52 (m, 3 H), 0.82 (d, J=6.82 Hz, 6 H).

The synthetic route of 1201676-03-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; WO2009/150230; (2009); 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 52559-11-2, name is Pyridine-2,3,4-triamine. This compound has unique chemical properties. The synthetic route is as follows. category: pyridine-derivatives

2-(4-Nitro-phenyl)-3H-imidazo[4,5-c]pyridine-6-ylamine (8): 2,4,5 Triaminopyridine (6, 0.660 g, 5.32 mmol), p-nitro benzoic acid (7, 0.888 mg 5.32 mmol) was taken in PPA (30 g) and heated at 180 C. for 7 h. The reaction mixture was cooled to room temperature and poured on to crushed ice. The excess PPA was neutralized carefully by addition of solid K2CO3 portion wise (caution) till effervescence ceased. The brownish green precipitate was filtered and washed with water and dried. The solid was taken in (CH2Cl2: MeOH:THF:NH4OH 50:30:17:3) mixture and filtered (repeated the process 3-4 times). The solvents were removed and the nitro amine precipitated with EtOAc to give 8 (0.575 g, 56%). 1H NMR (DMSO-d6; 500 MHz): delta11.10 (1H, brs), 8.77 (1H, s), 8.45-8.25 (4H m), 6.50 (1H, s), 5.67 (2H, brs); EIMS m/z: 256.4 (M+1) and 290 (M+Cl-);

With the rapid development of chemical substances, we look forward to future research findings about 52559-11-2.

Reference:
Patent; Sircar, Jagadish C.; Thomas, Richard J.; Richards, Mark L.; Sinha, Anjana; US2004/116466; (2004); 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. 98197-88-7, name is 2-(Hydroxymethyl)-4-nitropyridine. A new synthetic method of this compound is introduced below., Computed Properties of C6H6N2O3

A 100-mL round- bottomed flask open to air was charged with (4-nitropyridin-2-yl)methanol (1.03 g, 6.69 mmol), EtOH (17 mL), and EtONa (1.73 g, 25.4 mmol, 3.8 equiv). The vessel was fitted with a reflux condenser and heated to reflux. After 15 h, more EtONa (2.52 g, 37.0 mmol, 5.5 equiv) was added, and the reaction mixture was let stir at reflux. After 3 h, the reaction mixture was cooled to 23 C and neutralized with aqueous 4.0 M HCI. The mixture was concentrated in vacuo to remove organic solvent and then dissolved in saturated aqueous NaHCOa. The resulting aqueous layer was extracted with CH2CI2 (3 c 30 mL) using a separatory funnel. The combined organic layers were dried over anhydrous Na2S04, filtered, and concentrated in vacuo to afford (4-ethoxypyridin-2~yl)methanol (1.03 g, quantitative yield) as a red solid which was pure by 1H NMR.

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, 98197-88-7, 2-(Hydroxymethyl)-4-nitropyridine.

Reference:
Patent; UNIVERSITY OF PITTSBURGH – OF THE COMMONWEALTH SYSTEM OF HIGHER EDUCATION; KOIDE, Kazunori; BEIN, Kiflai; BRESSIN, Robert, Kruger; BURROWS, James, Proviano; GAMBINO, Adriana; LEIKAUF, George, D.; PHAM, Dianne; (80 pag.)WO2020/27905; (2020); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 709652-82-4, 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. 709652-82-4, name is 2-Amino-5-bromonicotinonitrile. A new synthetic method of this compound is introduced below.

In a vial was placed 2-amino-5-bromo-pyridine-3-carbonitrile (150 mg, 0.758 mmol), 4,4,5,5- tetramethyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3,2-dioxaborolane (288 mg, 1.14 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (11.7 mg, 0.015 mmol), and potassium acetate (149 mg, 0.515 mmol. Degassed ACN (9.5 mL) was added, and the reaction mixture was vacuum purged and back-filled with N2 (3X). The vial was capped, and the reaction mixture was microwaved at 150C for 30 min and then cooled to room temperature. To the reaction mixture was then added (5R,8S)- 8-(2-chloropyrimidin-4-yl)-3-(2,6-difluorophenyl)-9,9-dimethyl-5,6,7,8-tetrahydro-5,8-methanocinnoline (201 mg, 0.504 mmol), sodium carbonate (137 mg, 1.29 mmol), potassium acetate (74.3 mg, 0.757 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (11.7 mg, 0.015 mmol), and water (3.8 mL). The vial was recapped, and the reaction mixture was microwaved at 120C for 30 min and then filtered through a pad of Celite to rid Pd solid. The Celite pad was rinsed well with iPrOAc, and the filtrate was diluted with iPrOAc. The biphasic solution was separated. The organic layer was washed with water and brine, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The crude product was purified by silica gel chromatography eluted with methanol/isopropyl acetate followed by reverse phase prep-HPLC to give 120.4 mg of the title compound as a white solid. 1H NMR (DMSO- d6, 400 MHz): delta 9.21 (d, J = 2.3 Hz, 1H), 8.89 (d, J = 5.2 Hz, 1H), 8.69 (d, J = 2.3 Hz, 1H), 7.83 (s, 1H), 7.69- 7.57 (m, 2H), 7.47 (s, 2H), 7.35- 7.26 (m, 2H), 3.38- 3.23 (m, 2H), 2.49- 2.41 (m, 1H), 1.65- 1.56 (m, 1H), 1.33- 1.24 (m, 1H), 1.11 (s, 3H), 0.74 (s, 3H); LCMS ES+ 482.1 [M+1]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,709652-82-4, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; BRONNER, Sarah M.; CRAWFORD, James J.; CRIDLAND, Andrew; CYR, Patrick; FAUBER, Benjamin; GANCIA, Emanuela; GOBBI, Alberto; HURLEY, Christopher; KILLEN, Jonathan; LEE, Wendy; RENE, Olivier; VAN NIEL, Monique Bodil; WARD, Stuart; WINSHIP, Paul; ZBIEG, Jason; (439 pag.)WO2018/83105; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 6945-67-1, 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 6945-67-1, name is 2-Bromo-4-nitropyridine. This compound has unique chemical properties. The synthetic route is as follows.

The crude title compound from Step A above was dissolved in a mixture of degassed 1,4- dioxane (8.6 mL) and water (2 mL) in a microwave vial. Then [1 ,1 – bis(diphenylphosphino)ferrocene]dichloro-palladium(ll), complex with dichloromethane (0.034 g, 0.04 mmol), 2-bromo-4-nitropyridine (0.1 g, 0.49 mmol) and cesium carbonate (0.266 g, 0.82 mmol) were added and the reaction mixture was heated at ~115C in a sand- bath for 6 hours. The reaction mixture was diluted with ethyl acetate (100 mL) and water (30 mL), the organic phase separated, dried over Na2S04, filtered and the solvents evaporated in vacuo. The dark residue was purified by chromatography on silica (25 g puriFlash, Interchim) using a Biotage Isolera system employing an ethyl acetate/n-heptane gradient (5/95 -> 100/0 -> 100/0) to afford a mixture of the title compound and byproducts (0.076 g). Step C (0435) The mixture of the title compound from Step B above and byproducts (0.076 g) was dissolved in dichloromethane (10 mL) and trifluoroacetic acid (2.4 mL) was added. The reaction mixture was stirred at room temperature for 6 hours and then methanol was added (10 mL). The solvents were evaporated in vacuo and the residue suspended in methanol (10 mL). The solvents were again evaporated in vacuo and the residue suspended in dichloromethane (4 mL). After the addition of triethylamine (2 mL, 14.4 mmol), di-tert-butyl dicarbonate (0.2 g, 0.86 mmol), and 4-(dimethylamino)-pyridine (0.0036 g, 0.028 mmol), the reaction mixture was stirred at room temperature for 18 hours. The reaction mixture was diluted with ethyl acetate (100 mL) and water (40 mL). The organic phase was separated, dried over Na2S0 , filtered and the solvents removed in vacuo. The residue was purified on silica (25 g puriFlash, Interchim) using a Biotage Isolera One purification system employing an ethyl acetate/n-heptane gradient (5/95 -> 100/0 -> 100/0) to afford the Comparative Example C9 (F-9) Precursor and the byproduct as ~1.1-mixture (0.0231 g, pale yellow solid). 1H-NMR (400 MHz, CDCI3) delta = 9.38 (d, 1 H), 9.35 (d, 1 H), 9,31 (s, 2Eta), 9.02 (d, 1 H), 8.76- 8.70 (m, 5H), 8.68 (d, 1 H), 8.55 (d, 1 H), 8.43-8.37 (m, 3H), 8.12 (dd, 1 H), 8.07 (dd, 1 H), 7.43 (d, 1 H), 7.41 (d, 1 H), 1.82 (s, 18H) (0436) MS (ESI): m/z = 291.94 [MH-Boc of the title compound]*, 170.04 [MH+-Boc of byproduct]*

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 6945-67-1, 2-Bromo-4-nitropyridine.

Reference:
Patent; AC IMMUNE S.A.; PIRAMAL IMAGING SA; KROTH, Heiko; MOLETTE, Jerome; DARMENCY, Vincent; SCHIEFERSTEIN, Hanno; MUeLLER, Andre; SCHMITT-WILLICH, Heribert; BERNDT, Mathias; ODEN, Felix; GABELLIERI, Emanuele; (93 pag.)WO2018/15549; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 59020-10-9, 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.59020-10-9, name is 3-(Tributylstannyl)pyridine, molecular formula is C17H31NSn, molecular weight is 368.1447, as common compound, the synthetic route is as follows.

General procedure: 4.Aryl halide (0.5 mmol), base (1 mmol), CuI (20 mol %), alkylstannylpyridine(0.75 mmol), and catalyst (1 mol %) were dissolvedin DMF (2 mL) in a 10 mL vial and heated at a specific temperatureunder N2 for 12 h. After the reaction was complete, and thenquenched with water. The mixture was diluted with ethyl acetate(10 mL), filtered through a pad of Celite, and followed by extractionwith ethyl acetate for three times. The combined organic layer wasdried over anhydrous Na2SO4, filtered, and evaporated under reducedpressure. The residual was purified by flash chromatographyon silica gel (ethyl acetate/hexane) to give the desired product.3.12 1-[4-(Pyridin-3-yl)phenyl]ethanone (3la) 19 Yellow solid, mp 74-75 C; 1H NMR (400 MHz, CDCl3): delta=8.89 (s, 1H), 8.66 (s, 1H), 8.07 (d, J=7.96 Hz, 2H), 7.91 (d, J=7.52 Hz, 1H), 7.68 (d, J=7.92 Hz, 2H), 7.40-7.42 (m, 1H), 2.65 (s, 3H); 13C NMR (100 MHz, CDCl3): delta=26.7, 123.7, 127.3, 129.1, 134.5, 135.4, 136.5, 142.3, 148.3, 149.3, 197.5; HRMS-ESI (m/z): [M+H]+ calcd for C13H12NO+: 198.0913, found: 198.0918.

The chemical industry reduces the impact on the environment during synthesis 59020-10-9, I believe this compound will play a more active role in future production and life.

Reference:
Article; Ma, Gaizhi; Leng, Yuting; Wu, Yusheng; Wu, Yangjie; Tetrahedron; vol. 69; 2; (2013); p. 902 – 909;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1033810-70-6, [1,2,4]Triazolo[1,5-a]pyridin-7-ol, 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, Recommanded Product: 1033810-70-6, blongs to pyridine-derivatives compound. Recommanded Product: 1033810-70-6

The mixture of l-fluoro-2-methyl-4-nitrobenzene (96 mg, 0.617 mmol), [l,2,4]triazolo[l,5-a]pyridin-7-ol (100 mg, 0.740 mmol) aid cesium carbonate (482 mg, 1.48 mmol) in dimethyl sulfoxide (2.5 ml) was stirred at 80 C for 3 hr. The resulting mixture was poured into ice water and the precipitate was filtered and dried using blowing nitrogen gas to give 4-([l,2,4]triazolo[l,5-a]pyridin-7-yloxy)-3-methylaniline as a brown solid (145 mg, 87 %).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1033810-70-6, [1,2,4]Triazolo[1,5-a]pyridin-7-ol, and friends who are interested can also refer to it.

Reference:
Patent; DANA-FARBER CANCER INSTITUTE, INC.; GRAY, Nathanael S.; JANG, Jaebong; JANNE, Pasi; SON, Jieun; (116 pag.)WO2019/241715; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem