Category: pyridine-derivatives

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. 132865-44-2, name is 5-Chloro-6-methoxynicotinaldehyde, the common compound, a new synthetic route is introduced below. Computed Properties of C7H6ClNO2

A mixture of 5-chloro-6-methoxynicotinaldehyde (59.56 mg, 0.347 1 mmol), 4-(2-(3,6- diazabicyclo[3. 1.1 ]heptan-3 -yl)pyrimidin-5 -yl)-6-(2-morpholinoethoxy)pyrazolo[ 1,5 -a]pyridine3-carbonitrile (Intermediate P117; 31 mg, 0.069 mmol) and NaBH(AcO)3 (147.1 mg, 0.6943 mmol) in DCM (694.3 tL) was stirred overnight at ambient temperature. The reaction mixture was purified directly by silica chromatography (using 0-10% MeOH in EtOAc with 0.1% NH4OH as the gradient eluent) to cleanly afford the title compound (15.19 mg, 35% yield). MS (apci) m/z = 602.3 (M+H).

The synthetic route of 132865-44-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ANDREWS, Steven W.; ARONOW, Sean; BLAKE, James F.; BRANDHUBER, Barbara J.; COOK, Adam; HAAS, Julia; JIANG, Yutong; KOLAKOWSKI, Gabrielle R.; MCFADDIN, Elizabeth A.; MCKENNEY, Megan L.; MCNULTY, Oren T.; METCALF, Andrew T.; MORENO, David A.; TANG, Tony P.; REN, Li; (668 pag.)WO2018/71447; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 153034-78-7, 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 153034-78-7, name is 2-Fluoro-3-iodo-5-methylpyridine. This compound has unique chemical properties. The synthetic route is as follows.

In a 20-ml flask, 2-fluoro-3-iodo-5-methylpyridine (1.0 g, 4.2 mmol), potassium acetate (828 mg, 8.4 mmol), acetic acid (1 ml) and aniline (393 mg, 4.2 mmol) were mixed, and the solution was heated to reflux for 10 hours. After allowing the solution to stand overnight at room temperature, aniline (393 mg, 4.2 mmol) was added, and the mixture was further heated to reflux for 10 hours. After allowing the mixture again to stand overnight at room temperature, aniline (393 mg, 4.2 mmol) was added, and the mixture was further heated to reflux for 8 hours. This reaction solution was cooled to room temperature, ethyl acetate (20 ml) was added thereto. The organic layer was separated and washed with water (5 ml) two times. The organic layer was washed twice with a saturated aqueous sodium bicarbonate solution (10 ml) and further washed with saturated brine (10 ml) . The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure, diisopropyl ether (about 50 ml) was added to the residue, and a precipitate was filtered off. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (hexane : ethyl acetate = 4:1). The obtained extract was concentrated under reduced pressure, and dried under reduced pressure at 50C, to yield the title compound (539 mg, 1.7 mmol) as a yellow oily material (yield 41.2%) . 1H-NMR (CDCl3, TMS, 300 MHz) delta (ppm) : 2.17 (s, 3H), 6.77 (brs, IH), 6.98-7.03 (m, IH), 7.28-7.34 (m, 2H), 7.53-7.57 (m, 2H), 7.77-7.79 (s, 2H), 7.96-7.97 (m, IH).13C-NMR (CDCl3, TMS, 300 MHz) delta (ppm) : 17 . 04 , 81 . 16, 119.57 , 122 .48 , 125.72 , 128. 99, 140. 60, 147 .20, 147 .93, 151 . 92 High resolution mass spectrometry (Ci2HiIlN2 )Theoretical value : 308 .9889 [M-H] + Measured value : 309. 9892 [M-H] +

According to the analysis of related databases, 153034-78-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; WO2008/16184; (2008); 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. 607373-83-1, name is 2-Chloro-4-methoxy-5-nitropyridine. This compound has unique chemical properties. The synthetic route is as follows. COA of Formula: C6H5ClN2O3

Under nitrogen, Example 23B (70 mg, 0.42 mmol), 2-chloro-4-methoxy-5-nitropyridine (94 mg, 0.5 mmol), Pd2 (dba)3 (38 mg , 0.04 mmol), Xantphos (24 mg, 0.04 mmol) and cesium carbonate (271 mg, 0.83 mmol) in dioxane (5mL) were stirred at 90 deg.C for 12 hours. LCMS showed the reaction was complete. After the reaction mixture was diluted with water (40mL) (50mL × 2) and extracted with dichloromethane. The organic layer was washed with brine (30mL × 2), dried over anhydrous sodium sulfate, filtered and concentrated. The resulting residue was purified by silica gel column (petroleum ether: ethyl acetate = 4: 1, 3: 1) to give the title compound (50mg, yield 37.5%) as a yellow oil.

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, 607373-83-1, 2-Chloro-4-methoxy-5-nitropyridine.

Reference:
Patent; Nanjing Mingde New Drug Research and Development Co. Ltd.; Qilu Pharmaceutical Co., Ltd.; Ding, Zhaozhong; Zhang, Minghui; Chen, Shuhui; Liu, Xile; Zhu, Yidong; Fan, Chuanwen; Zhao, Baoping; Zhang, Long; Chen, Dong; Yang, Yingying; Zheng, Qingmei; Zheng, Shansong; Wan, Haiwen; Hu, Jinqing; (93 pag.)CN105330698; (2016); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 944401-65-4, Adding some certain compound to certain chemical reactions, such as: 944401-65-4, name is 5-Bromo-6-fluoropyridin-2-amine,molecular formula is C5H4BrFN2, 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 944401-65-4.

A solution of sodium nitrite (21.67g, 314.13mmol) in water (150mL) was added dropwise to a stirred mixture of 5-bromo-6-fluoropyridin-2-amine (50g, 261.78mmol) and sulphuric acid (1.2mL, 22.51mmol) in water (750mL) at 0-5C. The resulting suspension was stirred for 48 h at ambient temperature then the precipitate collected by filtration, washed with water (200mL) and dried under vacuum to afford the desired material (40. Og, 80%) as a pale yellow solid, which was used without further purification. NMR Spectrum: 1H NMR (300MHz, DMSO-d6) delta 6.55 (1H, d), 8.00 (1H, t), 11.71 (1H, bs). Mass Spectrum: m/z (ES+)[M+H]+ = 192.

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. 944401-65-4, 5-Bromo-6-fluoropyridin-2-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; BARLAAM, Bernard Christophe; PIKE, Kurt Gordon; WO2015/170081; (2015); A1;,
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.84249-14-9, name is 2-Amino-4-bromopyridine, molecular formula is C5H5BrN2, molecular weight is 173.0106, as common compound, the synthetic route is as follows.Quality Control of 2-Amino-4-bromopyridine

To a solution of potassium 2-chloro-3 -ethoxy-3 -oxoprop-l-en-l-olate (13.0 g, 68.9 mmol) and 4-bromopyridin-2-amine (3.00 g, 17.3 mmol) in ethanol (60 mL) was added cone. H2SO4 (2 mL). The reaction mixture was stirred at 90 C for 18 h and concentrated in vacuo. The residue was adjusted to pH = 10 with a saturated NaHCO, aqueous solution, and extracted with EtOAc (200 mL x 3). The combined organic phases were washed with brine (100 mL), dried over anhydrous Na2S04, and concentrated in vacuo. The residue was purified by a silica gel column chromatography (EtOAc/PE (v/v) = 1/4) to give the title compound as a white solid (4.6 g, 99%).MS (ESI, pos. ion) m/z: 269.1 [M+H]+;1H NMR (400 MHz, CDCb): d (ppm) 9.17 (d, J= 7.3 Hz, 1H), 8.26 (s, 1H), 7.92 (d, 7= 1.1 Hz, 1H), 7.14 (dd, J= 7.3, 1.6 Hz, 1H), 4.41 (q, J= 7.1 Hz, 2H), 1.42 (t, J= 7.1 Hz, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,84249-14-9, 2-Amino-4-bromopyridine, and friends who are interested can also refer to it.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; CALITOR SCIENCES, LLC; XI, Ning; LI, Minxiong; PENG, Ju; LI, Xiaobo; ZHANG, Tao; HU, Haiyang; CHEN, Wuhong; BAI, Changlin; KE, Donghua; CHEN, Peng; (281 pag.)WO2019/99311; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 918516-27-5, 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.918516-27-5, name is 5-(4-Chlorophenyl)-1H-pyrrolo[2,3-b]pyridine, molecular formula is C13H9ClN2, molecular weight is 228.68, as common compound, the synthetic route is as follows.

To a suspension of 5-(4-chlorophenyl)-1H-pyrrolo[2,3-b]pyridine (6b) (100 mg, 0.44 mmol) and N-(2,4-difluoro-3-formylphenyl)propane-1-sulfonamide (5) (139 mg, 0.53 mmol) in methanol (7.0 mL) was added potassium hydroxide (197 mg, 3.5 mmol). The reaction mixture was stirred at room temperature for 3 d and then evaporated to dryness. The crude reaction mixture was diluted with water (5.0 mL) and the pH adjusted to 7 with 4.0 N hydrochloric acid (10 mL). The resulting mixture was then diluted with water (25 mL) and extracted with ethyl acetate (3 x 20 mL). The combined organic layers were dried over sodium sulphate and evaporated in vacuo to give a crude solid (as a 2:1 mixture of the -OMe and free-OH 7b).

The chemical industry reduces the impact on the environment during synthesis 918516-27-5, I believe this compound will play a more active role in future production and life.

Reference:
Article; Buck, Jason R.; Saleh, Sam; Imam Uddin, Md.; Manning, H. Charles; Tetrahedron Letters; vol. 53; 32; (2012); p. 4161 – 4165;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 90902-84-4, 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. 90902-84-4, name is 2,5-Dibromopyridin-3-amine, molecular formula is C5H4Br2N2, 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.

(c) 1,1-Dimethylethyl (7-bromo-2-oxo-l,2,3,4-tetrahydro-l,5-naphthyridin-3- yl)carbamate; Zinc powder (0.934 g, 14.28 mmol) and iodine (0.054 g, 0.214 mmol) were heated in an evacuated flask which was then flushed with nitrogen 3 times. Methyl N- {[(l,l-dimethylethyl)oxy]carbonyl}-3-iodo-D-alaninate (2.35 g, 7.14 mmol, Aldrich Chemicals ) was dissolved in dry DMF (11.74 mL) and transferred via syringe to the reaction mixture which was previously cooled to 00C (reaction complete after 1.5h). The ice bath was removed and 2,5-dibromo-3-pyridinamine (2.392 g, 9.50 mmol) was added followed by bis (triphenylphosphine)palladium(II) chloride (0.251 g, 0.357 mmol) and the mixture heated at 40 0C for 14h. The mixture was cooled down and filtered through Celite, washing with EtOAc. Solvent was removed in vacuum. The mixture was redisolved in DMF (10 mL) and potassium carbonate (1.283 g, 9.28 mmol) was added. The resulting mixture was stirred at 80 0C for 6h. The mixture was concentrated and diluted with EtOAc, washed with water and brine and dried over Mg2SO4. Solvent was removed and the mixture chromatographed on silica eluting with 0-100% EtOAc :hexane to give the title compound (1.8 g, 5.26 mmol, 73.7 % yield) as light yellow solid. MS (ES+) m/z 343(MH+).

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 90902-84-4, 2,5-Dibromopyridin-3-amine.

Reference:
Patent; GLAXO GROUP LIMITED; WO2008/128961; (2008); A1;,
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.105752-11-2, name is 3-Amino-4-iodopyridine, molecular formula is C5H5IN2, molecular weight is 220.0111, as common compound, the synthetic route is as follows.name: 3-Amino-4-iodopyridine

Step 1: 4-[(2-fluorophenyl)ethvnyl]pyridin-3-amineTo a solution of 3-amino-4-iodopyridine in Dioxane/DMF (1 :1, 0.7M) were sequentially added NEt3 (5eq.), CuI (0.04 eq.), trans-bis(triphenylphosphine) palladium(II) chloride (0.02 eq.) and l-ethynyl-2-fluorobenzene (2 eq.). After heating for 1 h at 70 0C, water was added and the mixture was extracted with Et2O. The combined organic layers were washed with brine, dried over Na2SO4, filtered and the solvent was evaporated in vacuo. The residue was purified by chromatography on silica gel, eluting with PE/EtOAc (50:50), affording the title compound(80%) as a solid. 1H NMR (400 MHz, OMSO-d6 + TFA, 300K) delta, 7.26-7.33 (dd, 2H, J = 7.6 Hz, J= 8 Hz), 7.52-7.53 (m, IH), 7.78 (d, IH, J= 8 Hz), 7.83 (t, IH, J= 6.4 Hz), 7.7 (d, IH, J= 5.6 Hz), 8.21 (s, IH); MS (ES+) m/z 213 (M +H)+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,105752-11-2, 3-Amino-4-iodopyridine, and friends who are interested can also refer to it.

Reference:
Patent; ISTITUTO DI RICERCHE DI BIOLOGIA MOLECOLARE P. ANGELETTI S.P.A.; NARJES, Frank; HABERMANN, Jorg; COLARUSSO, Stefania; WO2010/115901; (2010); A1;,
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.159307-02-5, name is 6-Acetylpicolinonitrile, molecular formula is C8H6N2O, molecular weight is 146.15, as common compound, the synthetic route is as follows.Application In Synthesis of 6-Acetylpicolinonitrile

Compound 4b:to 100 ml by adding three-necked bottle of 2-cyano-6-acetyl-pyridine (3.00g, 20 . 53mmol), 2,6-dimethyl aniline (2.74g, 22 . 58mmol), the toluene sulphonic acid monohydrate (195 mg, 1 . 03mmol), solvent toluene and 50 ml, reflux device installed, heating reaction refluxing 48h. Cooling to room temperature, vacuum concentration, rapid column chromatography purification (ethyl acetate: petroleum ether = 1:20), to get the yellow oily matter (5.04g, 96%),

At the same time, in my other blogs, there are other synthetic methods of this type of compound,159307-02-5, 6-Acetylpicolinonitrile, and friends who are interested can also refer to it.

Reference:
Patent; Shanghai Institute of Organic Chemistry; Huang, Zheng; Zuo, Ziqing; Zhang, Lei; (50 pag.)CN105294667; (2016); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 13091-23-1, 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. 13091-23-1, name is 4-Chloro-3-nitropyridine. A new synthetic method of this compound is introduced below.

Ammonia gas (100 mL) was condensed into THF (300 mL) at -78C in a cardice/acetone bath. Potassium tert- butoxide (395 mmol, 44.25 g) was then added portion-wise with stirring. After 5 minutes, the cardice bath was lowered so only the bottom quarter of the flask was immersed and stirring was continued for a further 20 minutes. Concurrently, tert-butyl hydroperoxide (158 mmol, 26.3 mL) was added to a suspension of 4-chloro-3- nitropyridine (158 mmol, 25 g) in THF (100 mL) cooled in an ice/water bath. This mixture was stirred for 45 minutes then transferred to a dropping funnel and added drop-wise over 1.25 hours to the ammonia solution (0797) prepared above. The mixture was stirred for a further 3 hours then saturated aqueous ammonium chloride solution (35 mL) was added carefully. The mixture was allowed to warm to room temperature overnight allowing the ammonia to vent to atmosphere. The solvents were then removed under reduced pressure and the residue triturated with ice-cold saturated aqueous ammonium chloride solution (50 mL) . The resulting solid was collected by filtration, washed with ice-cold water (2 x 50 mL) then dried under suction prior to further drying by azeotroping with toluene (5 x 100 mL) then in a vacuum oven at 40C overnight to give the title compound as a brown solid (24.96 g, 90%) .

At the same time, in my other blogs, there are other synthetic methods of this type of compound,13091-23-1, 4-Chloro-3-nitropyridine, and friends who are interested can also refer to it.

Reference:
Patent; ONO PHARMACEUTICAL CO., LTD.; SAITO, Tetsuji; HIGASHINO, Masato; KAWAHARADA, Soichi; LEWIS, Arwel; CHAMBERS, Mark Stuart; RAE, Alastair; HIRST, Kim Louise; HARTLEY, Charles David; WO2015/115673; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem