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. 1513-66-2, name is 2,3-Difluoropyridine. This compound has unique chemical properties. The synthetic route is as follows. Formula: C5H3F2N

12.8 g of 2-chloro-3-aminopyridine was suspended in 120 mL of 60% aqueous hexafluorophosphoric acid, and 9.0 g sodium nitrite was added little by little thereto at 0C to precipitate crystals. The crystals were collected by filtration and washed with diethyl ether to give 15.75 g diazonium salt. Subsequently, the diazonium salt was suspended in 100 mL xylene and heated at 85C for 3 hours, 28 mL triethylamine was added thereto, and the reaction mixture was diluted with an aqueous saturated sodium bicarbonatesolution and then extracted with ethyl acetate. The extract was washed with brine, and the organic layer was dried over anhydrous sodium sulfate and then filtered through silica gel. The ethyl acetate was removed, and to the resulting xylene solution was added 6.0 mL 2-aminoethanol, and the mixture was heated at 130C for 10 hours. Then, the same procedure as in Production Example 231 was carried out, whereby 385 mg of the title compound (yellowoil) was obtained as a mixture.1H-NMR (CDCl3) delta: 3.60-3.68(m, 2H), 3.84(t, J=4.8Hz, 2H), 6.52-6.60(m, 1H), 7.12-7.20(m, 1H), 7.80-7.85(m, 1H)

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, 1513-66-2, 2,3-Difluoropyridine.

Reference:
Patent; Eisai Co., Ltd.; EP1382603; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 73290-22-9, 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.73290-22-9, name is 2-Bromo-5-iodopyridine, molecular formula is C5H3BrIN, molecular weight is 283.89, as common compound, the synthetic route is as follows.

General procedure: Step 1: 1-(6-Bromo-pyridin-3-yl)-4,4-dimethyl-imidazolidin-2-one [0137]2-bromo-5-iodopyridine (1.0 g, 3.52 mmol), 4,4-dimethyl-imidazolidin-2-one (CAS 24572-33-6) (400 mg, 3.52 mmol, 1.0 equiv.), cesium carbonate (1.72 g, 5.28 mmol, 1.5 equiv.), and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (xantphos) (82 mg, 0.141 mmol, 0.04 equiv.) in 10 ml of toluene was added under argon atmosphere tris(dibenzylideneacetone)dipalladium(0) chloroform adduct (Pd2 (dba)3*CHCl3) (73 mg, 0.07 mmol, 0.02 equiv.). The mixture was stirred for 1 hour at 100 C. The mixture was directly loaded on a 50 g silicagel column and was eluted with an heptan:ethyl acetate gradient 100:0 to 0:100 and an ethyl acetate:methanol gradient 100:0 to 80:20. The desired 1-(6-bromo-pyridin-3-yl)-4,4-dimethyl-imidazolidin-2-one (810 mg, 85% yield) was obtained as a light yellow solid, MS: m/e=207.1/272.1 (M+H+).

The chemical industry reduces the impact on the environment during synthesis 73290-22-9, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Hoffmann-La Roche Inc.; Jaeschke, Georg; Lindemann, Lothar; Ricci, Antonio; Rueher, Daniel; Stadler, Heinz; Vieira, Eric; US2013/90332; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 70201-43-3, 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.70201-43-3, name is 3-Bromoisonicotinaldehyde, molecular formula is C6H4BrNO, molecular weight is 186.0061, as common compound, the synthetic route is as follows.

To a solution of 5-methoxy-1-indanone (0.32 mmol) and 3-bromo-4-pyridinecarboxaldehyde (0.36 g, 2 mmol) in toluene (30 mL) was added p-toluenesulfonic acid (0.45 g, 2.4 mmol). After heated atreflux using a Dean-Stark for 4h, the mixture was cooled to room temperature and the solvent was removed in vacuum, then 5% sodium bicarbonate solution was added until pH 8. After extraction with dichloromethane (4x), the organic layer was dried over magnesium sulfate and concentrated to dryness. The residue was taken up with EtOAc and the solid was filtered, rinsed with EtOAc to afford the title compound 91 as a yellow solid (Yield 330 mg, 50%).1fl NMR (300 MHz, CDC13, 6): 3.91 (br s, 5H), 6.96-7.00 (m, 2H), 7.49 (d, 1H, J 5,1 Hz), 7.74(t, 1H, J= 2.4 Hz), 7.87 (d, 1H, J= 8.4 Hz), 8.58 (d, 1H, J= 5.1 Hz), 8.82 (s, 1H).?3C NMR (75 MHz, CDCI3, 6): 31.7, 55.8, 109.8, 115.8, 123,5, 126.7, 128.2, 131.1, 141.2, 143.1, 148.3, 152.3, 153.0, 165.8, 191.3.

The chemical industry reduces the impact on the environment during synthesis 70201-43-3, I believe this compound will play a more active role in future production and life.

Reference:
Patent; INSA (INSTITUT NATIONAL DES SCIENCES APPLIQUEES) DE ROUEN; CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE (CNRS); UNIVERSITE DE ROUEN; VFP THERAPIES; MARSAIS, Francis; LEVACHER, Vincent; PAPAMICAEL, Cyril; BOHN, Pierre; PEAUGER, Ludovic; GEMBUS, Vincent; LE FUR, Nicolas; DUMARTIN-LEPINE, Marie-Laurence; WO2014/114742; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 72990-37-5 ,Some common heterocyclic compound, 72990-37-5, molecular formula is C6H4ClNO, 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 solution of 6-methoxy-2-methylquinoline (200 mg, 1.15 mmol), p-toluenesulfonamide (197 mg, 1.15 mmol) and 3-chloroisonicotinaldehyde (163 mg, 1.15 mmol) in toluene (5 mL) was refluxed at 120 C. for 12 h in a reaction tube under N2. After the mixture was cooled to room temperature, the solvent was removed under reduced pressure. Then the concentrate was purified by column chromatography with EtOAc/Hexane (1:4, v/v) on silica gel, affording TZ-36-48 as a yellow solid (255 mg, 65%). 1H NMR (400 MHz, CDCl3) delta 8.61 (s, 1H), 8.47 (d, J=5.1 Hz, 1H), 8.07 (dd, J=16.7, 8.9 Hz, 2H), 7.87 (d, J=16.4 Hz, 1H), 7.72 (d, J=8.5 Hz, 1H), 7.65-7.54 (m, 2H), 7.39 (d, J=9.2 Hz, 1H), 7.28-7.21 (m, OH), 7.07 (s, 1H), 3.91 (d, J=13.2 Hz, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,72990-37-5, its application will become more common.

Reference:
Patent; Washington University; Tu, Zhude; Li, Junfeng; Yue, Xuyi; Kotzbauer, Paul; (100 pag.)US2017/189566; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 874302-76-8, 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.874302-76-8, name is 4-nitrophenyl 2-(pyridin-2-yldisulfanyl)ethyl carbonate, molecular formula is C14H12N2O5S2, molecular weight is 352.39, as common compound, the synthetic route is as follows.

To a solution of compound 2 (10 mg, 0.028 mmol) and doxorubicin hydrochloride (12 mg, 0.020 mmol) in DMF (1 mL) under N2, DIPEA (8 jiL, 0.028 mmol) is added at room temperature and stirred for 16 h. Then, the solvent is evaporated and the residue is purified by flash chromatography (eluent: CH2C12/MeOH 20:1) to obtain compound 3(Figure 3) as red solid in 90% yield; 1H NMR (500 MHz, CDC13) oe 13.94 (s, 1H), 13.18(s, 1H), 8.40 (d, J= 3.8 Hz, 1H), 8.00 (d, J 7.6 Hz, 1H), 7.76 (t, J 8.0 Hz, 1H), 7.70(d, J 7.5 Hz, 1H), 7.63 (t, J 7.4 Hz, 1H), 7.37 (d, J= 8.5 Hz, 1H), 7.07 (t, J= 1H),5.50 b(s, 1H), 5.26 (dd, J= 3.7, 2.0 Hz, 1H), 5.15 (d, J= 8.8 Hz, 1H), 4.74 b(s, J 21.4Hz, 2H), 4.56 (bs, 1H), 4.42 – 4.34 (m, 1H), 4.21 – 4.08 (m, 2H), 4.06 (s, 3H), 3.81 (m,1H), 3.62 (bs, 1H), 3.22 (dd, J= 18.8, 1.5 Hz, 1H), 3.14-2.86 (m, 5H), 2.33 (d, J14.6 Hz, 1H), 2.15 (dd, J= 15.0, 3.6 Hz, 1H), 1.81 (m, 2H), 1.48 – 1.42 (m, 2H), 1.29(d, J 6.5 Hz, 3H); 13C NMR (126 MHz, CDC13) oe 213.9, 187.0, 186.6, 161.0, 160.1,156.2, 155.6, 155.2, 149.8, 149.4, 137.3, 135.7, 135.4, 133.6, 133.6, 120.9, 120.8,119.9, 119.8, 118.4, 111.5, 111.4, 100.9, 69.7, 69.0, 67.4, 65.6, 63.5, 56.7, 53.4, 47.0,37.5, 35.6, 33.9, 30.0, 29.7, 28.3, 17.0; MS (ESI): mlz (%)757(100), (figures 13 and14).

Statistics shows that 874302-76-8 is playing an increasingly important role. we look forward to future research findings about 4-nitrophenyl 2-(pyridin-2-yldisulfanyl)ethyl carbonate.

Reference:
Patent; FUNDACION IMDEA NANOCIENCIA; LOPEZ CORTAJARENA, Aitziber; SOMOZA CALATRAVA, Alvaro; COULEAUD, Pierre; OCAMPO GARCIA, Sandra; AIRES TRAPOTE, Antonio; LATORRE LOZANO, Alfonso; (66 pag.)WO2016/150521; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 4548-45-2, 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. 4548-45-2, name is 2-Chloro-5-nitropyridine. A new synthetic method of this compound is introduced below.

N-BOC piperazine (0.5g) and 2-chloro-5-nitropyridine (0.424g) in DMF (16ml) were treated with potassium carbonate (0.744g) and DIPEA (1.41ml). The resulting mixture was heated at 1200C for 4 hours.After cooling to room temperarure, the solvent was removed in vacuo and the residue partitioned between ethyl acetate and water. Organic layer washed again with water then dried over anhydrous magnesium sulphate. After filtration, the solvent evaporated to dryness in vacuo to afford the title compound as a pale brown solid in 95%.LCMS (ES+) 209.05 (MH+-BOC)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,4548-45-2, its application will become more common.

Reference:
Patent; GLAXO GROUP LIMITED; WO2006/94840; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 108281-79-4, 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.108281-79-4, name is 6-Bromo-[1,2,4]triazolo[4,3-a]pyridine, molecular formula is C6H4BrN3, molecular weight is 198.02, as common compound, the synthetic route is as follows.

To a solution of 6-bromo-[1,2,4]triazolo[4,3-a]pyridine (35 mg, 0.18 mmol) in anhydrous THF (1 mL) was added n-BuLi (0.15 mL, 0.38 mmol) dropwise at -65 C. under N2, then it was maintained at this temperature for 3 h. To this solution was added dropwise a solution of 1-(3-(N-methoxy-N-methylcarbamoyl)benzyl)quinazoline-2,4(1H,3H)-dione (50 mg, 0.15 mmol) in THF (1 mL), then it was stirred for 4 h at -65 C. It was allowed to warm to 0 C. for over 4 h. The reaction solution was poured into saturated aqueous NH4Cl, extracted with ethyl acetate (3*10 mL). The combined organic layers were washed with brine, dried over anhydrous Na2SO4, and concentrated. The crude product was purified by preparative TLC to give the title compound (6.5 mg, 11% yield) as white solid. 1H NMR (CD3OD+CDCl3): 9.42 (d, J=7.2 Hz, 1H), 8.41-8.39 (m, 2H), 8.10 (d, J=7.2 Hz, 1H), 7.95 (d, J=9.0 Hz, 1H), 7.58-7.45 (m, 4H), 7.18-7.11 (m, 3H), 5.38 (s, 2H). MS: m/z 398.2 [M+H]+.

The chemical industry reduces the impact on the environment during synthesis 108281-79-4, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Impact Therapeutics, Inc.; Cai, Sui Xiong; Tian, Ye Edward; Dong, Haijun; Xu, Qingbing; Wu, Lizhen; Liu, Lijun; Jiang, Yangzhen; Bao, Qingli; Wang, Guoxiang; Yin, Feng; Gu, Chengyun; Hu, Xiuhua; Wang, Xiaozhu; Kang, Sishun; Chen, Shengzhi; US2014/23642; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 36052-26-3, 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 36052-26-3, name is Methyl 6-aminopicolinate. This compound has unique chemical properties. The synthetic route is as follows.

To a stirred solution of methyl 6-aminopicolinate (1 eq.) in CHCI3 (0.5 M) is added bromine (1 eq. ). The reaction is stirred for 12 h at room temperature. Afterwards, the reaction mixture is washed with saturated sodium thiosulfate and water. The organic phase is washed with brine, dried over Na2SO4, filtered, and concentrated to dryness. The crude product was purified on silicagel (Gradient: 0 – 75% EtOAc in hexane) to provide 1 and 2 as a white solids, m/z 232 (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 36052-26-3, Methyl 6-aminopicolinate.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BOEHRINGER INGELHEIM PHARMA GMBH & CO. KG; WO2009/140101; (2009); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 53636-65-0, 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. 53636-65-0, name is 5-Methylpyridine-2,3-dicarboxylic acid, molecular formula is C8H7NO4, 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.

EXAMPLE 44 Preparation of 5-chloromethyl-2,3-pyridinedicarboxylic acid anhydride STR107 A solution of 75.0 g (0.41 m) of 5-methyl-2,3-pyridinedicarboxylic acid in 500 mL of 1,2-dimethoxyethane is treated with 125 g acetic anhydride (1.2 m) and 81 g pyridine (1.02 m). The resulting solution is stirred for 18 hours at room temperature. The solution is stripped in vacuo to leave 70.3 g (100%) of 5-methyl-2,3-pyridinedicarboxylic acid anhydride.

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 53636-65-0, 5-Methylpyridine-2,3-dicarboxylic acid.

Reference:
Patent; American Cyanamid Company; US5334576; (1994); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem