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. 944401-77-8, name is 2-Amino-4-fluoropyridine, the common compound, a new synthetic route is introduced below. name: 2-Amino-4-fluoropyridine

Step 1. 5-bromo-4-fluoropyridin-2-amine To a solution of 4-fluoropyridin-2-amine (400 mg, 3.57 mmol) in acetonitrile (35. 7 mL) was added NBS (648 mg, 3.64 mmol) in three portions at 0 C. The reaction mixture was stirred at 0 C. for 20 min. LCMS showed the reaction complete. After quenched with sat Na2S2O3 and NaHCO3, stirred for 30 min. The reaction mixture was extracted with EtOAc 3 times. Washed by sat NaHCO3, water and brine. Dried and concentrated. The crude material was triturated with ether and taken to the next step without further purification. LCMS (m/z): 192.9 (MH+), 0.32 min.

The synthetic route of 944401-77-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Novartis AG; Bagdanoff, Jeffrey T.; Ding, Yu; Han, Wooseok; Huang, Zilin; Jiang, Qun; Jin, Jeff Xianming; Kou, Xiang; Lee, Patrick; Lindvall, Mika; Min, Zhongcheng; Pan, Yue; Pecchi, Sabina; Pfister, Keith Bruce; Poon, Daniel; Rauniyar, Vivek; Wang, Xiaojing Michael; Zhang, Qiong; Zhou, Jianguang; Zhu, Shejin; (366 pag.)US9242996; (2016); B2;,
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.58584-86-4, name is Ethyl 2,6-dichloronicotinate, molecular formula is C8H7Cl2NO2, molecular weight is 220.05, as common compound, the synthetic route is as follows.Recommanded Product: 58584-86-4

(a) Ethyl6-{4-[(benzylsulfonyl)carbamoyl]piperidin-1-yl}-2-chloronicotinate A micro wave vial was charged with DIPEA (2.73 g, 21.1 mmol), ethyl2,6-dichloronicotinate (Example 43(a)) (1.547 g, 7.03 mmol), N-(benzylsulfonyl)piperidine-4-carboxamide (Example 6(d)) (2.28 g, 8.08 mmol) and DMF and the mixture was heated to 120 C. for 10 minutes followed by 150 C. for 10 minutes using microwave single node heating. Ratio of the two possible regioisomers was ca. 1:1 together with some bis-addition adduct. The crude product was purified by first using HPLC (Kromasil C8, 10 mum, using a gradient of MeCN with an acidic second eluent (H2O/MeCN/AcOH, 95/5/0.1)) followed by flash chromatography using a stepwise gradient of heptane/EtOAc 1/1 then heptane/EtOAc 1/1+0.15% FA and finally heptane/EtOAc 1/2+0.15% FA. (Rf product (heptane/EtOAc 1/2+0.15% FA)=0.47) to give ethyl6-{4-[(benzylsulfonyl)carbamoyl]piperidin-1-yl}-2-chloronicotinate. Yield: 610 mg (19%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,58584-86-4, Ethyl 2,6-dichloronicotinate, and friends who are interested can also refer to it.

Reference:
Patent; AstraZeneca AB; US2008/171732; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 884495-37-8, 2-Chloro-5-fluoropyridin-3-amine, 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: 2-Chloro-5-fluoropyridin-3-amine, blongs to pyridine-derivatives compound. Recommanded Product: 2-Chloro-5-fluoropyridin-3-amine

A degassed solution of 2-chloro-5-fluoro-3-amino-pyridine (3.5 g), 4- (4,4,5,5-tetramethyl-[l,3,2]dioxaborolan-2-yl)-3,6-dihydro-2/f-pyridine-l-carboxylic acid tert-butyl ester (8.89 g) (prepared as described in WO 2006/003494) and bis(triphenylphosphine)palladium(II) chloride (0.84 g) in dioxane (157 ml) was treated with a degassed solution of sodium carbonate (7.6 g) in water (72 ml). The reaction mixture was stirred at reflux for 1 hour, cooled to ambient temperature and the solvent evaporated in vacuo. The residue was diluted with ethyl acetate, washed with water and brine, dried over sodium sulfate and concentrated in vacuo. Chromatography on silica gel (eluent: cyclohexane / ethyl acetate 8:2) afforded 3-amino-5-fluoro-3′,6′-dihydro-2’H-[2,4′]bipyridinyl-r-carboxylic acid tert-hutyl ester (4.6 g) as a solid. MS (ES+) 294 (MEta+), 238 (M-isoprene); IH NMR (400 MHz, CDCl3) 1.48 (s, 9H), 2.53 (m, 2H), 3.64 (t, 2H), 3.99 (m, 2H), 4.08 (m, 2H), 5.99 (m, IH), 6.70 (dd, IH), 7.85 (d, IH).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,884495-37-8, 2-Chloro-5-fluoropyridin-3-amine, and friends who are interested can also refer to it.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; PITTERNA, Thomas; CASSAYRE, Jerome Yves; CORSI, Camilla; MAIENFISCH, Peter; WO2010/9968; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 88912-26-9, Adding some certain compound to certain chemical reactions, such as: 88912-26-9, name is 2,5-Dichloroisonicotinic acid,molecular formula is C6H3Cl2NO2, 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 88912-26-9.

To a methanolic solution of 2, 5-dichloro- isonicotinic acid was added H2SO4 (cone) (0.5 mL) and the solution was heated to reflux for 12 h. The mixture was cooled to room temperature, neutralized with aqueous NaHCO3, extracted into EtOAc and evaporated to afford the methyl ester (6-2) in 89% yield.

According to the analysis of related databases, 88912-26-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BIOTA SCIENTIFIC MANAGEMENT PTY LTD; WO2008/141385; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 885276-93-7 ,Some common heterocyclic compound, 885276-93-7, molecular formula is C10H9BrN2O2, 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.

Synthesis of fR)-ethyl 5-(2-(3-cvano-5-fluoroDhenyl)-4A-difluoroDyrrolidin-1- yl)pyrazolo[1,5-alpyridine-3-carboxylate (X-8)[000304] A N2 purged flask was charged with ethyl 5-bromopyrazolo[1 ,5-a]pyridine-3- carboxylate (100 mg, 0.37 mmol), palladium acetate (1 .7 mg, 7 muiotaetaomicronIota), xantphos (7 mg, 1 1 muiotaetaomicronIota), cesium carbonate (170 mg, 0.52 mmol), 1 ,4-dioxane (0.5 ml_) and (R)-3- (4,4-difluoropyrrolidin-2-yl)-5-fluorobenzonitrile (I-24) (84 mg, 0.37 mmol). The contents were heated to 140 C for 1 hour under microwave irradiation. Upon cooling to room temperature the reaction was partitioned with EtOAc and water. The organic layer was washed with water, brine, dried over magnesium sulfate, filtered and reduced to dryness. The crude product was purified by column chromatography on silica gel with EtOAc/hexanes gradient as eluant to yield (R)-ethyl 5-(2-(3-cyano-5- fluorophenyl)-4,4-difluoropyrrolidin-1 -yl)pyrazolo[1 ,5-a]pyridine-3-carboxylate (X-8). 1 H NMR (400MHz, CDCI3) delta 8.26 (d, J = 7.6 Hz, 1 H), 8.24 (s, 1 H), 7.38 (s, 1 H), 7.33 – 7.29 (m, 1 H), 7.25 -7.21 (m, 1 H), 6.93 (d, J = 2.8 Hz, 1 H), 6.19 (dd, J = 2.8, 7.6 Hz, 1 H), 5.14 (dd, J = 4.4, 9.2 Hz, 1 H), 4.34 – 4.25 (m, 2 H), 4.25 – 4.16 (m, 1 H), 4.05 – 3.93 (m, 1 H), 3.14 – 2.98 (m, 1 H), 2.53 – 2.42 (m, 1 H), 1 .34 (t, J = 7.2 Hz, 3 H). MS m/z 415.1 (M+1 )+.

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. 885276-93-7, Ethyl 5-bromopyrazolo[1,5-a]pyridine-3-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; IRM LLC; MOLTENI, Valentina; FAN, Yi; LOREN, Jon; SMITH, Jeffrey M.; FLATT, Brenton T.; WO2012/116217; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 868733-96-4, 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. 868733-96-4, name is 2-Boc-Amino-3-iodo-4-chloropyridine. A new synthetic method of this compound is introduced below.

A suspension of (4-chloro-3-iodo-pyridin-2-yl)-carbamic acid tert-butyl ester (5.6 g, 15.8 mmol) in 48% hydrobromic acid was heated at 100 C. for 10 min to give a clear solution. The mixture was cooled, treated with crushed ice and made basic with 6 M NaOH. The precipitated product was collected by vacuum filtration, washed with H2O and sucked partially on the funnel to give a white solid. The product was dissolved in THF and the solution dried over MgSO4 and concentrated in vacuo to give the title compound (3.7 g, 93%) as a white solid. 1H NMR (DMSO-d6) delta 7.84 (d, 1H, J=5.1 Hz), 6.73 (d, 1H, J=5.6 Hz), 6.51 (br s, 2H); MS (ESI+): m/z 254.97 (M+H)+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,868733-96-4, 2-Boc-Amino-3-iodo-4-chloropyridine, and friends who are interested can also refer to it.

Reference:
Patent; Borzilleri, Robert M.; Cornelius, Lyndon A.M.; Schmidt, Robert J.; Schroeder, Gretchen M.; Kim, Kyoung S.; US2005/245530; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 100704-10-7, 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 100704-10-7, name is (2-Chloropyridin-4-yl)methanol. This compound has unique chemical properties. The synthetic route is as follows.

Example 43A 2-Chloro-4-(chloromethyl)pyridine 1.00 g (6.97 mmol) of (2-chloropyridin-4-yl)methanol was dissolved in 40 ml of methylene chloride, 10 ml of thionyl chloride were slowly added at RT and the mixture was stirred at RT overnight. The mixture was then concentrated on a rotary evaporator and the residue was stirred in a mixture of methylene chloride and aqueous sodium bicarbonate solution. The phases were separated and the methylene chloride phase was dried over anhydrous magnesium sulfate, filtered and concentrated on a rotary evaporator. 1.10 g (97% of th.) of the title compound were obtained. 1H-NMR (400 MHz, CDCl3, delta/ppm): 8.49 (d, 1H), 7.38 (s, 1H), 7.27-7.22 (m, 1H), 4.52 (s, 2H). LC/MS (method E, ESIpos): Rt=1.43 min, m/z=162 [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 100704-10-7, (2-Chloropyridin-4-yl)methanol.

Reference:
Patent; BAYER SCHERING PHARMA AKTIENGESELLSCHAFT; Haerter, Michael; Beck, Hartmut; Ellinghaus, Peter; Berhoerster, Kerstin; Greschat, Susanne; Thierauch, Karl-Heinz; Suessmeier, Frank; US2013/196964; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 159981-19-8, 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. 159981-19-8, name is 6-(2,2,2-Trifluoroethoxy)nicotinaldehyde, molecular formula is C8H6F3NO2, 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.

n-Butyllithium (5.14 mL, 13.4 mmol) is added to a suspension of methyltriphenylphosphonium bromide (4.41 g, 12.34 mmol) in tetrahydrofuran (51 mL) at -78 oC under nitrogen atmosphere . The reaction mixture is warmed to room temperature to yield deep red ylide solution. To ylide solution, cooling in ice, is introduced 6-(2,2,2-trifluoroethoxy)nicotinaldehyde (2.11 g, 10.3 mmol, Step-1) in tetrahydrofuran (10 mL) and stirred at room temperature for 3 hours. The reaction mixture is poured into water, extracted with ethyl acetate and dried over sodium sulfate and concentrated in vacuo. The residue is purified by column chromatography on silica gel eluting with n-hexane / ethyl acetate (10:1) to give 1.56 g (75% yield) of the title compound as colorless oil.1H-NMR (300 MHz, CDCl3) delta 8.10 (1H, d, J = 2.6 Hz), 7.75 (1H, dd, J = 8.4, 2.6 Hz), 6.84 (1H, d, J = 8.4 Hz), 6.65 (1H, dd, J = 17.6, 11.0 Hz), 5.68 (1H, d, J = 17.6 Hz), 5.27 (1H, d, J = 11.0 Hz), 4.76 (2H, q, J = 8.4 Hz), MS (ESI) m/z: 204 (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 159981-19-8, 6-(2,2,2-Trifluoroethoxy)nicotinaldehyde.

Reference:
Patent; RAQUALIA PHARMA INC.; YAMAGISHI, Tatsuya; KAWAMURA, Kiyoshi; ARANO, Yoshimasa; MORITA, Mikio; WO2012/53186; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1060811-62-2, 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 1060811-62-2, name is 4,6-Dichloronicotinaldehyde. This compound has unique chemical properties. The synthetic route is as follows.

To a stirred solution of 4,6-dichloronicotinaldehyde (3 x 1.0 g, 1.0 eq) in DME (3 x 14 mL), hydrazine hydrate (3 x 1.14 g, 4.0 eq, 99percent) was added slowly in a vial. The vial was sealed and the contents heated at 75°C for 16 h. After TLC showed completion, the mixture was cooled to rt and diluted with water (3 x 10 mL) and EtOAc (3 x 10 mL). After combining all 3 mixtures, the layers were separated and the organic layer was washed with brine (20 mL), dried over anhydrous sodium sulphate, filtered and concentrated. The resulting crude was purified by flash chromatography (Combiflash® – Redisep, 12 g) using MeOH in DCM as eluent. The desired product was eluted at 1percent MeOH in DCM. The fractions with product were concentrated to obtain pure 6-chloro- lH-pyrazolo[4,3-c]pyridine as yellow solid (1.4 g, 53.43percent, from 3 batches). 1H NMR (400 MHz, DMSO-d6): delta 13.608 (s, 1H), 8.946 (s, 1H), 8.350 (s, 1H), 7.652 (s, 1H). LCMS calculated for (M) 423.15 and found (M+H) 424.23.

According to the analysis of related databases, 1060811-62-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASANA BIOSCIENCES, LLC; VENKATESAN, Aranapakam M.; SMITH, Roger A.; THOMPSON, Scott K.; LAPING, Nicholas; KULKARNI, Bheemashankar; HALLUR, Gurulingappa; VISWANADHAN, Vellarkad N.; PENDYALA, Muralidhar; KETHIRI, Raghava Reddy; TYAGI, Rajiv; SIVANANDHAN, Dhanalakshmi; BAKTHAVATCHALAM, Rajagopal; WO2015/38417; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 5350-93-6, 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.5350-93-6, name is 6-Chloropyridin-3-amine, molecular formula is C5H5ClN2, molecular weight is 128.56, as common compound, the synthetic route is as follows.

A mixture of 3-amino-6-chloropyridine (12.5 g, 98 mmol) and potassium thiocyanate (80 g, 820 mmol) in glacial acetic acid (200 mL) was cooled with ice bath. Bromine (0.6 mL, 11.6 mmoi) was added dropwise. The resulting mixture was stirred at O°C for 1 h and room temperature overnight. Water (100 mL) was added to the mixture, and heated at 85°C. The mixture was filtered, while stifl warm. The solid was collected and washed with warm acetic acid. The combined filtrate was brought to basic by careful addition of ammonium hydroxide. DCM was added to the mixture. The aqueous layer was separated and extracted with DCM. The organic layer was combined, dried (MgSO4), filtered and concentrated. The residue was purified with silica gel column to give 11.2 g (61percent) of a white solid as the desired product 164a.

The chemical industry reduces the impact on the environment during synthesis 5350-93-6, I believe this compound will play a more active role in future production and life.

Reference:
Patent; SCHERING CORPORATION; PALANI, Anandan; RAO, Ashwin, U.; CHEN, Xiao; SHAO, Ning; HUANG, Ying, R.; ASLANIAN, Robert, G.; WO2010/71819; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem