Category: pyridine-derivatives

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. 884495-38-9, name is 6-Chloro-4-methylnicotinaldehyde. This compound has unique chemical properties. The synthetic route is as follows. SDS of cas: 884495-38-9

General procedure: To a solution of Intermediate 47B (1.00g. 8.92 mrnol) and 6bromo4 methylnicotinonitrile (1.76 g, 8.92 mmol) in dioxane (20 mL) was added K2C03 (308 g. 22.30mmol) and XANTPHOS (1.03 g, 1.78 mmol) and the resulting reaction mixture was degassed with nitrogen for 5 minutes. Pd2(dha)3 (0.82 g, 089 mmol) was added and the resulting mixture was degassed again for 5 minutes then heated at 100 C for 16 h. The reaction mixture was cooled to ambient temperature, filtered t1i?ough Celite and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography (Redisep40 g, 22. 5%MeOHDCM) to obtain Intermediate 47C (120 g, 59.0%) as a pale yellow solid. 1H NMR (300 MHz, DMSO-d6) ppm 2.57 (s. 3 H) 2.65 (t, J= 6.61 Hz, 2 H) 3.55 3.67 (m, 2 H) 4.71 (br. s., I H) 7.80 (s, I H) 7.96 (d, J= 0.76 Hz, I H) 8.47 (s, I H) 8.82 (s, I H). LCMS Qvlethod-D):retention time 086 mm, [M±ij 229.3.

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, 884495-38-9, 6-Chloro-4-methylnicotinaldehyde.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; GUNAGA, Prashantha; BHIDE, Rajeev S.; BORA, Rajesh Onkardas; PANDA, Manoranjan; YADAV, Navnath Dnyanoba; PRIESTLEY, Eldon Scott; RICHTER, Jeremy; (321 pag.)WO2018/93569; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 63996-36-1 , The common heterocyclic compound, 63996-36-1, name is 2-(4-Bromophenyl)pyridine, molecular formula is C11H8BrN, 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.

967 mg (4.10 mmoL) of Compound J, 759 mg (4.14 mmoL) of phenoxazine, 28 mg (0.123 mmoL) of Pd(OAc)2, 99 mg (0.492 mmoL) of P(t-Bu)3, and 569 mg (5.92 mmoL) of NaOt-Bu are dissolved in 40 mL of toluene, and the mixture is heated to 110 C., and the temperature is maintained until the reaction is terminated. When the reaction is terminated, the resultant is subjected to a work-up procedure and column chromatography to obtain Compound K (yield: 80%).

The synthetic route of 63996-36-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Samsung Electronics Co., Ltd.; Yang, Hae Yeon; Son, Jun Mo; Ju, Won Jae; (34 pag.)KR101594129; (2016); B1;,
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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. 135124-71-9, name is 5-(Hydroxymethyl)nicotinonitrile, the common compound, a new synthetic route is introduced below. name: 5-(Hydroxymethyl)nicotinonitrile

To a solution of 5-(hydroxymethyl)pyridine-3-carbonitrile (2 g, 14.91 mmol) in DCM (10 mL) was added hydrogen chloride in dioxane (4M, 5 mL) and concentrated. To the residue was added SOCl2(6.50 mL, 89.61 mmol) and stirred for 3 hr at 60 C. After cooling, toluene (200mL) was added and the mixture was filtered. The filtrate was adjusted to pH = 7 with sat. NaHCCh and extracted with DCM (3 x 50 mL). The organic phase was combined and dried over Na2S04and then concentrated under reduced pressure to give 5-(chloromethyl)pyridine-3- carbonitrile (l .7g, 74.72% yield) as a black solid.

The synthetic route of 135124-71-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ARBUTUS BIOPHARMA, INC.; BI, Yingzhi; DORSEY, Bruce D.; FAN, Yi; MOORE, Christopher Brooks; NGUYEN, Duyan; (169 pag.)WO2019/191624; (2019); 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. 13472-84-9, name is 3-Chloro-2-methoxypyridine. A new synthetic method of this compound is introduced below., Recommanded Product: 3-Chloro-2-methoxypyridine

General procedure: An oven-dried reaction flask, equipped with a reflux condenser was charged with heteroaryl chloride (1.0 mmol), 4-(N-Boc-N-methyl)aminopiperidine (1.3 equiv.), Pd(OAc)2 (3 mol%), DavePhos (3 mol%), t-BuONa (1.2 equiv.). The flask was sealed, and was evacuated and backfilled with argon for three times. Then 3 mL toluene was added to the system with a syringe. The reaction mixture was stirred at 120 C for 12 h. After cooling to the room temperature, the resulting residue was filtered through a plug of silica gel and washed with ethyl acetate. The mixture was then poured into water and extracted. The combined organic layers were washed with brine, dried over MgSO4, and filtered. The solvent was removed under vacuum. The residue was purified by flash column chromatography to afford the desired product.

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, 13472-84-9, 3-Chloro-2-methoxypyridine.

Reference:
Article; Zhang, Kena; Li, Hui; Li, Jingya; Zou, Dapeng; Wu, Yangjie; Wu, Yusheng; Tetrahedron Letters; vol. 58; 20; (2017); p. 1976 – 1979;,
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Electric Literature of 1160791-13-8, 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.1160791-13-8, name is 2-Amino-6-bromothiazolo[5,4-b]pyridine, molecular formula is C6H4BrN3S, molecular weight is 230.09, as common compound, the synthetic route is as follows.

Step 2: l-allyl-3- (6-bromothiazolo [5,4-b] pyridin-2-yl) urea (Intermediates). In a 25 ml round-bottomed flask, 6-bromothiazolo [5,4-b] pyridin-2-amine (0.575 g, 2.5 mmol) was suspended in tetrahydrofuran (15 mL). To this triethylamine (0.697 mL,5.00 mmol) was added in one portion and resulting reaction mixture was stirred at RT.Then allyl isocyanate (0.331 mL, 3.75 mmol) was added and stirred at RT for overnight.The reaction mixture was evaporated in vacuo, ice-cold water was added, sonicated well and the precipitated solid was filtered and dried under high vacuum. The crude product was triturated with acetonitrile gave the pure product as brown solid (0.650mg, 83%).MS (ES+): 314 for C10H9BrN4OS1H NMR (DMSO-d6) delta: 3.82 (t, 2H,CH2); 5.10 -5.25(m, 2H,CH2); 5.80 -5.95(m,IH5CH); 6.95 (t, IH5NH); 8.15 (bs, IH5NH); 8.23 (s, lH,Aro.); 8.48 (s, lH,Aro.).

The chemical industry reduces the impact on the environment during synthesis 1160791-13-8, I believe this compound will play a more active role in future production and life.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2009/147431; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 2604-39-9 , The common heterocyclic compound, 2604-39-9, name is 2-Chloro-5-nitropyridin-4-amine, molecular formula is C5H4ClN3O2, 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.

NBS (564 mg, 3.17 mmol) was added to a solution of 1 (500 mg, 2.88 mmol) in 8 mL of AcOH. The resulting mixture was stirred at 60 C for 4 h. After cooled to room temperature, the mixture was diluted with water. The precipitate was collected by filtration to afford 580 mg of 2 as a yellow solid, which was used in the next step without further purification. [M+Hj : 251.91, 253.96.

The synthetic route of 2604-39-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF MICHIGAN; WANG, Shaomeng; ZHANG, Dengyou; ZHENG, Canhui; CHEN, Zhuo; LIU, Liu; HUANG, Liyue; YANG, Chao-Yie; (110 pag.)WO2018/213211; (2018); A1;,
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Pyridine | C5H5N – PubChem

Electric Literature of 1206968-88-8, 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.1206968-88-8, name is (5-Bromo-3-chloropyridin-2-yl)methanol, molecular formula is C6H5BrClNO, molecular weight is 222.467, as common compound, the synthetic route is as follows.

DMP (45.83g, 102.lOmmoI) was added portion wise to a stirred solution of (5-bromo-3-chloropyridin-2-yl)-methanol (16g, 72.O7mmoI) in DCM (320mL) at 0C and stirred for 16h at RT. The RM was filtered through celite and washed with DCM (3x100mL).The filtrate was washed with Aq.NaHCO3 (200mL), water (200mL), brine(250mL), dried (Na2SO4), filtered, concentrated under reduced pressure to give crude. The crude was purified by CC (0-5% EtOAc in PE) to give 5-bromo-3-chloropicolinaldehyde (lOg, 66%) as light yellow solid.

The chemical industry reduces the impact on the environment during synthesis 1206968-88-8, I believe this compound will play a more active role in future production and life.

Reference:
Patent; GRUeNENTHAL GMBH; SCHUNK, Stefan; REICH, Melanie; JAKOB, Florian; DAMANN, Nils; HAURAND, Michael; KLESS, Achim; ROGERS, Marc; SUTTON, Kathy; WO2015/158427; (2015); A1;,
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Pyridine | C5H5N – PubChem

Electric Literature of 73406-50-5, Adding some certain compound to certain chemical reactions, such as: 73406-50-5, name is Ethyl 3-hydroxypicolinate,molecular formula is C8H9NO3, 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 73406-50-5.

2-(pyrrolidin-1-yl)carbonyl-3-hydroxy pyridine 18 g (0.093 moles) of ethyl-3-hydroxypicolinate [J. Heterocyclic Chem. 23, 665, 1986] were cooled at -5 C. and ml 250 of pyrrolidine were added under nitrogen atmosphere. After the addition, the solution was allowed to reach room temperature, stirred 24 h and then evaporated in vacuo to give 15 g of the title compound as a slight yellow oil which crystallized on standing.

According to the analysis of related databases, 73406-50-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Dr. L. Zambeletti SpA; US5089507; (1992); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 722550-01-8, 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 722550-01-8, name is 4-(Pyrrolidin-1-yl)pyridin-2-amine. This compound has unique chemical properties. The synthetic route is as follows.

A solution of 2-bromo-1-(5-chloro-2,4-dimethoxyphenyl)ethanone 3 (70 mg, 0.24 mmol) and 4-(pyrrolidin-1-yl)pyridin-2-amine 4a (39 mg, 0.24 mmol) in acetone (3 mL) was heated at 75 C for 16 h. The reaction mixture was cooled to room temperature; the white precipitate was collected by filtration, washed with acetone, and dried under reduced pressure to afford 2-(5-chloro-2,4-dimethoxyphenyl)-7-(pyrrolidin-1-yl)imidazo[1 ,2-a]pyridine hydrobromide 5a (45 mg, 43%) as a pink solid. 1H NMR (300 MHz, DMSO-d6) . delta 13.03 (s, 1H), 8.50 (d, J = 7.6 Hz, 1H). 8.20 (s, 1H), 7.89 (s, 1H), 6.97 (s, 1H), 6.95 (dd, J=2.2, 7.6 Hz, 1H), 6.30 (d, J= 2.0 Hz, 1H), 4.05 (s, 3H), 3.99 (s, 3H). 3.48-3.38 (m, 4H), 2.08- 1.98 (m, 4H); HPLC ( Method 4) 98.7% (AUG), tR = 19.02 min. APCI MS m/z 358 [M + H]+ .

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 722550-01-8, 4-(Pyrrolidin-1-yl)pyridin-2-amine.

Reference:
Patent; ONCOTHERAPY SCIENCE, INC.; MATSUO, Yo; HISADA, Shoji; NAKAMURA, Yusuke; CHAKRABARTI, Anjan; RAWAT, Manish; RAI, Sanjay; SATYANARAYANA, Arvapalli, Venkata; DUAN, Zhiyong; TALUKDAR, Arindam; RAVULA, Srinivas; DECORNEZ, Helene; (491 pag.)WO2017/58503; (2017); A1;,
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Application of 73177-35-2, Adding some certain compound to certain chemical reactions, such as: 73177-35-2, name is 2-Methyl-1H-pyrrolo[3,2-b]pyridine,molecular formula is C8H8N2, 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 73177-35-2.

Example 2 (see general route 2, procedure E, F, C and D)2-(l-(4-chlorobenzyl)-2-methyl-lH-pyrrolo[3,2-b]pyridin-3-yl)-N-(2-methoxypyridin- 4-yl)-2-oxoacetamide (3) [00252] To a solution of 2-methyl-lH-pyrrolo[3,2-b]pyridine (74.4 mg, 0.563 mmol) and 4-chlorobenzyl chloride (0.0780 mL, 0.619 mmol) in DMSO (8 mL) at room temperature was added powdered potassium hydroxide (69.5 mg, 1.24 mmol). The reaction was stirred at room temperature for 12 hours, after which LCMS analysis indicated that the reaction was complete. The reaction mixture was diluted in water and extracted with dichloromethane (3 x 50 mL), dried (sodium sulfate), filtered and concentrated to a clear residue. Purification was achieved by silica gel chromatography using 30 to 90% ethyl acetate in hexanes over 80 minutes affording l-(4-chlorobenzyl)-2 -methyl- lH-pyrrolo[3,2-b]pyridine (64.2 mg, 0.250 mmol, 44% yield) as an off-white solid. NMR (400 MHz, CDC13) delta (ppm): 8.41 (dd, 1H), 7.41 (d, 1H), 7.24 (d, 2H), 7.01 (dd, 1H), 6.86 (d, 2H), 6.54 (s, 1H), 5.27 (s, 2H), 2.41 (s, 3H).[00253] To a solution of l-(4-chlorobenzyl)-2-methyl-lH-pyrrolo[3,2-b]pyridine (341 mg, 1.33 mmol) in dichloromethane (25 mL) was added aluminum trichloride (886 mg, 6.65 mmol). The mixture was stirred at room temperature for 20 minutes, after which ethyl oxalyl chloride (0.744 mL, 6.65 mmol) was added. The reaction mixture was stirred at room temperature for an additional three hours, after which it was poured over ice and extracted with ethyl acetate (3 x 50 mL), dried (sodium sulfate) filtered and concentrated to afford 2-(l- (4-chlorobenzyl)-2-methyl-lH-pyrrolo[3,2-b]pyridin-3-yl)-2-oxoacetic acid (76.5 mg, 0.233 mmol, 18% yield) an off-white solild. This material was used without any purification in the next step. The intended product of this reaction, ethyl 2-(l-(4-chlorobenzyl)-2-methyl-lH- pyrrolo[3,2-b]pyridin-3-yl)-2-oxoacetate, was observed in trace amounts and was not isolated from the reaction mixture. NMR (400 MHz, CDC13) delta (ppm): 8.44 (dd, 1H), 7.41 (dd, 1H), 7.20 (d, 2H), 7.04 (dd, 1H), 6.84 (d, 2H), 6.54 (s, 1H), 5.27 (s, 2H), 2.77 (s, 3H)[Carboxylic acid proton not detected in 1H NMR]. LCMS: 2.18 min, [ES]” found 327.10.[00254] To a solution of 2-(l-(4-chlorobenzyl)-2-methyl-lH-pyrrolo[3,2-b]pyridin-3- yl)-2-oxoacetic acid (76.5 mg, 0.218 mmol) in acetonitrile (7 mL) was added triethylamine (0.304 mL, 2.18 mmol), 2-methoxypyridin-4-amine (29.8 mg, 0.240 mmol), followed by a 50% ethyl acetate solution of T3P (972 mg, 1.53 mmol). The reaction was heated to 60 C for 2 hours, after which additional triethylamine (0.304 mL, 2.18 mmol) and T3P solution (972 mg, 1.53 mmol) were added. The reaction mixture was stirred at 60 C for 12 hours, after which it was diluted in water, extracted with ethyl acetate (3 x 50 mL), dried (sodium sulfate), filtered and concentrated to a residue. Purification was achieved by silica gel chromatography (Luknova 40g, 20 mL/min) using 10 to 60% ethyl acetate in hexanes over 60 minutes. 2-(l-(4-chlorobenzyl)-2-methyl-lH-pyrrolo[3,2-b]pyridin-3-yl)-N-(2- methoxypyridin-4-yl)-2-oxoacetamide (31 mg, 0.071 mmol, 33% yield) was isolated as a light-tan solid. NMR (400 MHz, CDC13) delta (ppm): 12.5 (br. s, IH), 8.55 (dd, IH), 8.08 (d, IH), 7.55 (dd, IH), 7.23-7.29 (m, 4H), 7.18 (dd, IH), 6.87 (d, 2H), 5.34 (s, 2H), 3.90 (s, 3H), 2.70 (s, 3H).

According to the analysis of related databases, 73177-35-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; IRONWOOD PHARMACEUTICALS, INC.; HUDSON, Colleen; BARDEN, Timothy, C.; JIA, James; MERMERIAN, Ara; PENG, Bo; YANG, Jane; YU, Xiang, Y.; SPROTT, Kevin; WO2012/88469; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem