Month: April 2022

Reference of 72093-04-0, 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. 72093-04-0, name is 3-Chloro-4-methylpyridine. A new synthetic method of this compound is introduced below.

Example 33 Compounds GK-GL A solution of diisopropylamine (1.23 ML) in dry tetrahydrofuran (15 ML) is stirred and cooled to -70C under a nitrogen atmosphere. To this is added a 2.5 M solution of n-butyl lithium in hexanes (3.52 ML) at -70C. -The mixture is stirred for 30 minutes then a solution of 3-chloro-4-methylpyridine (1.02 g) in dry tetrahydrofuran (10 ML) is added. The mixture is stirred for a further 40 minutes. A solution of 3-cyclopentyloxy-4,N-dimethoxy-N-methylbenzamide (2.23 g; that is prepared as described Reference Example 64) in dry tetrahydrofuran (10 ML) is added and the mixture stirred at -70C for 30 minutes, -40C for 30 minutes, 0C for 30 minutes, and room temperature for 1 hour. A mixture of ethanol and hydrochloric acid 19:1 (40 ML) is added and then the reaction mixture is partitioned between brine (40 ML) and diethyl ether (40 ML). The ethereal phase is dried over sodium sulfate and concentrated in vacuo to give a pale yellow solid (3.0 g). The solid is triturated with diethyl ether and then purified by flash chromatography (ethyl acetate eluent on a silica gel column) to give a solid (1.6 g). The solid is triturated with diethyl ether, collected and dried to afford 2-(3-chloropyrid-4-yl)-1-(3-cyclopentyloxy-4-methoxyphenyl)ethanone (1.35 g) as a cream solid m.p. 124-125C. [Elemental analysis: C,66.2; H,5.89; N,4.12%; calculated for C1920lNO3 C,65.99; H,5.83; N,4.05%.]

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,72093-04-0, its application will become more common.

Reference:
Patent; RHONE-POULENC RORER LIMITED; EP741707; (1998); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 71670-70-7 ,Some common heterocyclic compound, 71670-70-7, molecular formula is C7H9Cl2N, 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 mixture of N-((1S,2S)-2-hydroxycyclohexyl)-7-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide (Intermediate 13), (110 mg), 2-(chloromethyl)-5-methylpyridine hydrochloride (72 mg) and cesium carbonate (302 mg) in DMF (3.6 mL) was stirred at rt overnight. The reaction mixture was filtered and the filtrate was reduced in vacuo. The residue was purified by column chromatography to give the desired compound (142 mg). LCMS: m/z 379.63 [M+H]+. 1H NMR (400 MHz, CDCl3) ppm 1.20-1.87 (m, 6H) 2.15 (d, J=11.5 Hz, 2H) 2.32 (s, 3H) 2.53 (s, 3H) 3.60 (d, J=3.3 Hz, 1H) 3.83-3.98 (m, 1H) 5.56-5.69 (m, 2H) 6.56 (d, J=6.2 Hz, 1H) 6.92 (d, J=3.9 Hz, 1H) 7.39 (d, J=7.7 Hz, 1H) 8.35 (d, J=4.7 Hz, 1H) 8.42 (s, 1H) 9.28 (d, J=6.4 Hz, 1H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,71670-70-7, its application will become more common.

Reference:
Patent; Payne, Andrew; Castro Pineiro, Jose Luis; Birch, Louise Michelle; Khan, Afzal; Braunton, Alan James; Kitulagoda, James Edward; Soejima, Motohiro; US2015/94328; (2015); 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. 505084-55-9, name is 2-Chloro-5-(trifluoromethyl)-4-iodopyridine. A new synthetic method of this compound is introduced below., category: pyridine-derivatives

Example 21; 5-(2-(2-methoxy-4-morpholinophenylamino)-5-(trifluoromethyl)pyridin-4- ylamino)-N-methylthiazole-4- carboxamide; 2-chloro-5-(trifluoromethyl)pyridin-4-amine; 2-chloro-4-iodo-5-(trifluoromethyl)pyridine was dissolved in 7 M Ammonia/Methanol. It was heated in a Biotage Initiator microwave synthesizer at 130 C for 1 h. A mixture of the 2- and 4-substituted products was obtained. The solvent was removed and the residue was purified by silica gel chromatography (DCM/MeOH) gradient. The pure title compound was isolated.

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, 505084-55-9, 2-Chloro-5-(trifluoromethyl)-4-iodopyridine.

Reference:
Patent; THE SCRIPPS RESEARCH INSTITUTE; WO2008/115369; (2008); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 145255-19-2, 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. 145255-19-2, name is 5-Aminopyridine-2-carboxamide. A new synthetic method of this compound is introduced below.

General procedure: 4-(2-chloro-9H-purin-6-yl)morpholine (50 mg, 0.21 mmol), heteroaromatic amine (1.2 equiv), 2 mol % Pd(OAc)2, 3 mol % Xantphos, Cs2CO3(140 mg, 0.43 mmol) in dioxane (1.5 mL) was heated to 160 C in a microwave reactor for 40 min. The solvent was removed under reduced pressure and the crude material was purified by column chromatography on silica gel with CH2Cl2/CH3OH in a 15:1 (v/v)ratio as eluent, to afford product 3m-p.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,145255-19-2, its application will become more common.

Reference:
Article; Tian, Chao; Han, Zifei; Li, Yuanxin; Wang, Meng; Yang, Jiajia; Wang, Xiaowei; Zhang, Zhili; Liu, Junyi; European Journal of Medicinal Chemistry; vol. 151; (2018); p. 836 – 848;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 851484-95-2 ,Some common heterocyclic compound, 851484-95-2, molecular formula is C6H3ClFNO, 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.

To a stirred solution of methyl 2-sulfanylbenzoate (2.5 g, 14.86 mmol) in DMF (30 ml)were added Cs2CO3 (7.267 g, 22.29 mmol) followed by 2-chloro-5-fluoropyridine-3-carbaldehyde (2.37 1 g, 14.86 mmol) and heated at 70C for 30 mm. The reaction mixture was diluted with water and extracted with ethyl acetate. The combined organic layers were washed with water, dried over anhydrous sodium sulfate and concentrated under vacuum. The crude thus obtained, was purified by silica gel column chromatography using ethyl acetate in n-hexane (0-6%) as an eluting solvent to afford methyl 2-[(5-fluoro-3-formylpyridin-2-yl)sulfanyl]benzoate (2.65 g, 61%) as off white solid. LC-MS: 292.0 [M+Hf?.

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. 851484-95-2, 2-Chloro-5-fluoronicotinaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; ALANINE, Alexander; BEIGNET, Julien; BLEICHER, Konrad; FASCHING, Bernhard; HILPERT, Hans; HU, Taishan; MACDONALD, Dwight; JACKSON, Stephen; KOLCZEWSKI, Sabine; KROLL, Carsten; SCHAEUBLIN, Adrian; SHEN, Hong; STOLL, Theodor; THOMAS, Helmut; WAHHAB, Amal; ZAMPALONI, Claudia; (623 pag.)WO2017/72062; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 190271-88-6, 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.190271-88-6, name is Methyl 2-chloro-5-nitronicotinate, molecular formula is C7H5ClN2O4, molecular weight is 216.58, as common compound, the synthetic route is as follows.

The fourth step of Scheme 4: To a 5 mL DMF solution of 2-chloro-5-nitronicotinic acid methyl ester (269 mg, 1.25 mmole) was added methyl thioglycolate (111 muL, 1.25 mmole) followed by potassium carbonate (428 mg, 3.1 mmole) and the mixture was stirred at room temperature overnight. The reaction mixture was then poured into 50 mL water and extracted with CH2Cl2. The aqueous phase was acidified with 2N HCl and extracted with CH2Cl2. Combined organic phases were washed with water and dried over MgSO4. The solids were removed by filtration and the solvent was evaporated under reduced pressure to give 240 mg (76%) 3-hydroxy-5-nitro-thieno[2,3-b]pyridine-2-carboxylic acid methyl ester as a tan colored solid. 1H NMR (400 MHz, CHLOROFORM-D) delta ppm 4.02 (s, 3H) 9.01 (d, J=2.53 Hz, 1H) 9.52 (d, J=2.53 Hz, 1H) 10.19 (s, 1H).

Statistics shows that 190271-88-6 is playing an increasingly important role. we look forward to future research findings about Methyl 2-chloro-5-nitronicotinate.

Reference:
Patent; Lee, Jinbo; Kirincich, Steve J.; Smith, Michael J.; Wilson, Douglas P.; Follows, Bruce C.; Wan, Zhao-Kui; Joseph-McCarthy, Diane M.; Erbe, David V.; Zhang, Yan-Ling; Xu, Weixin; Tam, Steve Y.; US2005/203081; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 116548-04-0, 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. 116548-04-0, name is 2-Oxo-6-(trifluoromethyl)-1,2-dihydropyridine-3-carbonitrile, molecular formula is C7H3F3N2O, 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.

2-Oxo-6-(trifluoromethyl)-1,2-dihydropyridine-3-carbonitrile 1 (5.0 g, 0.03 mol) and potassium carbonate (7.3 g, 0.05 mol) were taken in dry acetone(50 mL), stirred for 30 minutes at RT, followed by the addition of propargyl bromide (3.1 g, 0.03 mol) then catalytic amount of sodium iodide (NaI) was added. The mixture was continuously stirred for 6 h at RT. The progress of the reaction was monitored by TLC, and after completion of the reaction, acetone was removed under reduced pressure. The residue was treated with ice cold water (40 mL) and the aqueous layer was extracted twice with ethyl acetate (2 × 40mL). The combined organic phases were dried over Na2SO4 and evaporated on rotavapor. The resulted residue was purified using 60-120 mesh silica gel column chromatography. Yield 81% (Yellow liquid). FTIR (Neat): 2236 (CN), 2129 (C?C), 1583 cm-1(C=N); 1H NMR (CDCl3, 300 MHz): delta 2.48 (t, 1H, J = 2.26 Hz, C?C-H), 5.14 (d, 2H, J = 2.26 Hz, OCH2), 7.41 (d, 1H, J = 7.55 Hz, Ar-H), 8.10 (d, 1H, J = 7.55 Hz, Ar-H); 13C NMR (CDCl3, 75 MHz): delta 55.53 (O-CH2), 75.90 (Acetylene-C), 76.89 (Acetylene-C), 100.68 (C-CN) 113.51 (Ar-C), 113.80 (CN), 120.27 (q, J = 273.99 Hz) (CF3), 144.93 (Ar-C), 148.81 (q, J = 34.11 Hz) (C-CF3), 162.30 (Ar-C-O); ESI-MS: m/z 227 (M+1); HRMS: m/z Calcd for C10H6F3N2O ([M+H]+): 227.0124. Found: 227.0124.

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 116548-04-0, 2-Oxo-6-(trifluoromethyl)-1,2-dihydropyridine-3-carbonitrile.

Reference:
Article; Kumar, R. Naresh; Mallareddy; Nagender; Rao, P. Sambasiva; Poornachandra; Ranjithreddy; Kumar, C. Ganesh; Narsaiah; Indian Journal of Chemistry – Section B Organic and Medicinal Chemistry; vol. 55B; 11; (2016); p. 1361 – 1375;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 89488-30-2, 5-Bromo-3-methylpyridin-2(1H)-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, Recommanded Product: 89488-30-2, blongs to pyridine-derivatives compound. Recommanded Product: 89488-30-2

To a mixture of compound 4b2 (2 g, 10.6 mmol) and CH2CI2 (100 mL) is added Ag2CO3 (8.8 g, 31.9 mmol) and CH3I (7 mL, 112 mmol). The reaction mixture is stirred at room temperature overnight, then filtered through diatomaceous earth (Celite). The filtrate is concentrated under reduced pressure to give compound4b3.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,89488-30-2, 5-Bromo-3-methylpyridin-2(1H)-one, and friends who are interested can also refer to it.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BOEHRINGER INGELHEIM PHARMA GmbH & CO KG; WO2008/67644; (2008); 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 131747-62-1, name is 3-(Trifluoromethyl)pyridine-2-carboxaldehyde. This compound has unique chemical properties. The synthetic route is as follows. category: pyridine-derivatives

To a solution of 170 (150 mg, 0.7769 mmol) in toluene 15 ml was added 66 (203.9 mg, 1.165 mmol). PTSA (443.06 mg, 0.2337 mmol) was added to the reaction mass, which was stirred at 120 C. for 6 h. The reaction mass was diluted with ethyl acetate and washed with water (3×25 ml). The organic layer was dried over sodium sulphate and concentrated to get the crude, used for the next step without further purification.

With the rapid development of chemical substances, we look forward to future research findings about 131747-62-1.

Reference:
Patent; Vankayalapati, Hariprasad; Yerramreddy, Venkatakrishnareddy; US2015/72980; (2015); 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. 16328-62-4, name is 1H-Imidazo[4,5-b]pyridin-2(3H)-one. This compound has unique chemical properties. The synthetic route is as follows. COA of Formula: C6H5N3O

To a stirred solution of l,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (2.0 g, 14.8 mmol) in 20.0 mL of DMF was added NaFl (0.592 g, 14.8 mmol) at 0 C followed by stirring for 1 hour at 0 C. To this reaction mixture was added Boc anhydride (3.23 g, 14.8 mmol) at 0 C followed by stirring for 12 h at RT. The reaction mixture was quenched with water and extracted with ethyl acetate. The organic layer was washed with water and brine solution and dried over anhydrous sodium sulphate. The organic layer was concentrated to give the title compound (1.20 g, 34.58 %). NMR [300 MHz, DMSO-d6]: d 11.90 (bs, 1H), 8.03 – 8.02 (d, 1H), 7.83 – 7.81 (d, 1H), 7.10 – 7.06 (m, 1H), 1.58 (s, 9H).

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, 16328-62-4, 1H-Imidazo[4,5-b]pyridin-2(3H)-one.

Reference:
Patent; AURIGENE DISCOVERY TECHNOLOGIES LIMITED; CHIKKANNA, Dinesh; PANIGRAHI, Sunil Kumar; SAMMETA, Srinivasa Raju; GERD, Wohlfahrt; MIKKO, Myllymaki; (157 pag.)WO2019/180628; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem