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. 94805-51-3, name is 2-Oxo-1,2-dihydropyridine-4-carbonitrile. This compound has unique chemical properties. The synthetic route is as follows. HPLC of Formula: C6H4N2O

2-Hydroxy-4-cyano-pyridine (240 mg, 2 mmol, 1 equiv.) was dissolved in DMF (6 ml), K2CO3 (415 mg, 3 mmol, 1.5 equiv.) and NaI (60 mg, 0.4 mmol, 0.2 equiv.) were added and the mixture was stirred at r.t. for 10 min. 5-Chloro-2-(chloromethyI)-1,3- benzothiazole (436 mg, 2 mmol, 1 equiv.) was added and the reaction mixture was stirred at 600C for 3 h and at r.t. overnight. By addition of H2O, brown solid precipitated, which was filtered, rinsed with H2O, dried and re-crystallised from CH3CN. Yield 280 mg (46%), mp 224-227C, HPLC-MS (method 1): m/z 302 [M+H]+, Rt = 3.80 min. By 13C-NMR analysis it was identified to be the N-alkylated derivative (Scheme 24). The DMF-H2O mother liquors were evaporated to dryness under reduced pressure and the residue was purified by column chromatography on silica, eluted with EtOAc/hexane (10%-100% gradient) to give 45 mg (7.5% yield) of a brown solid, HPLC-MS (method 1): m/z 302 [M+H]+, Rt = 4.86 min. By 13C-NMR analysis, it was identified to be the desired O-alkylated derivative (Scheme 24).

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, 94805-51-3, 2-Oxo-1,2-dihydropyridine-4-carbonitrile.

Reference:
Patent; PROLYSIS LTD; WO2007/107758; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 73583-37-6, 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. 73583-37-6, name is 4-Bromo-2-chloropyridine, molecular formula is C5H3BrClN, 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.

tert-butyl (4-(2-chloropyridin-4-yl)phenyl)carbamateTo a mixture of (4-boc-aminophenyl)boronic acid (200mg, 0.84mmol) and 2-chloro-4- bromopyridine (162mg, 0.84mmol) in 10ml of 1,4-dioxane, was added PdCl2(PPh3)2 (10mg, 0.014mmol) and 1M Na2CO3 aqueous solution (0.5ml, 1.0mmol). The mixture was heated at 70 C under N2 for 2 hours, cooled to room temperature and poured into 100ml of water. The brown precipitates were filtered, washed with water and dried to give tert-butyl (4-(2- chloropyridin-4-yl)phenyl)carbamate as the crude product.

According to the analysis of related databases, 73583-37-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ALLERGAN, INC.; GUO, Xialing; ZHU, Zhen; WO2015/69287; (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. 19337-97-4, name is trans-3-(3-Pyridyl)acrylic acid. This compound has unique chemical properties. The synthetic route is as follows. Product Details of 19337-97-4

(2E)-3-(pyridin-3-yl)prop-2-enoic acid (698 mg, 4.68 mmol) was dissolved in DMF (24 mL) and treated with DIPEA (2 mL, 11.7 mmol) and HATU (1.80 g, 4.68 mmol). After 5 minutes, tert-butyl 4-(4-aminobutyl)piperidine-l -carboxylate (1.00 g, 3.90 mmol) was added as a solution in DMF (8 mL). The reaction was stirred at room temperature overnight. The reaction solvent was removed in vacuo, and the residue redissolved in EtOAc then washed once with water, twice with saturated NaHCC , and once with brine. The organic layer was dried over Na2S04 and concentrated. The crude product was purified by silica gel chromatography (EtOAc/hexanes) to provide the title compound (1.16 g, 3.00 mmol, 77%). LCMS: tR = 1.22 min; m/z = 388.3 [M+H]+. lH NMR (400 MHz, Chloroform-d) delta 8.78 – 8.71 (m, 1H), 8.57 (dd, J = 4.8, 1.6 Hz, 1H), 7.83 – 7.75 (m, 1H), 7.62 (d, J = 15.7 Hz, 1H), 7.35 – 7.29 (m, 1H), 6.45 (d, J = 15.7 Hz, 1H), 5.68 (t, 1H), 4.18 – 3.90 (m, 2H), 3.40 (td, J = 7.2, 5.9 Hz, 2H), 2.76 – 2.55 (m, 2H), 1.70 – 1.51 (m, 4H), 1.45 (s, 9H), 1.43 – 1.31 (m, 3H), 1.31 – 1.20 (m, 2H), 1.07 (qd, J = 12.5, 4.4 Hz, 2H).

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, 19337-97-4, trans-3-(3-Pyridyl)acrylic acid.

Reference:
Patent; SEATTLE GENETICS, INC.; NEUMANN, Christopher Scott; OLIVAS, Kathleen; (446 pag.)WO2018/75600; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 13959-02-9 , The common heterocyclic compound, 13959-02-9, name is 3-Bromoisonicotinic acid, molecular formula is C6H4BrNO2, 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.

General procedure: A mixture of theappropriate carboxylic acid (1.38 mmol) and 1,1′-carbonyldiimidazole(0.25 g, 1.52 mmol) in 1,4-dioxane (10 ml)was stirred for 30 min at 80, followed by the addition ofcompound 8l (0.36 g, 1.38 mmol) and stirring for 3 h at100. The substrate conversion was monitored by TLC(eluent CHCl3-MeOH, 7:3). After the reaction wascomplete, the solvent was evaporated under vacuum, and the product was isolated chromatographically (eluting withEtOAc in the case of compounds 9a,b,e, and with CHCl3-MeOH, 10:1 in the case of compounds 9,d).

The synthetic route of 13959-02-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Krolenko, Konstantin Yu.; Vlasov, Sergiy V.; Zhuravel, Irina A.; Chemistry of Heterocyclic Compounds; vol. 52; 10; (2016); p. 823 – 830; Khim. Geterotsikl. Soedin.; vol. 52; 10; (2016); p. 823 – 830,8;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 109205-68-7, name is 5-(Hydroxymethyl)pyridin-2(1H)-one, molecular formula is C6H7NO2, 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. Recommanded Product: 109205-68-7

STR18 2.0 g (0.016 mol) of 5-hydroxymethyl-2-pyridinone are added to a mixture of 6.7 g (0.032 mol) of phosphorus pentachloride and 2.5 g (0.016 mol) of phosphorus oxychloride, the mixture is stirred at reflux temperature for 7 hours, cooled and taken up in ethyl acetate, ice water is then added, the mixture is rendered neutral using sodium carbonate, the organic phase is separated off and dried over magnesium sulphate, and the solvent is removed under reduced pressure. The residue may be purified by distillation. 2.5 g (96% of theory) of 2-chloro-5-chloromethylpyridine of boiling point 70 C.-80 C. at 1 mbar are obtained.

With the rapid development of chemical substances, we look forward to future research findings about 109205-68-7.

Reference:
Patent; Bayer Aktiengesellschaft; US4958025; (1990); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 15862-37-0, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 15862-37-0 as follows.

43.00 g (152.52 mol) of 2,5-dibromo-3-nitropyridine are hydrogenated in 1.5 g of Pd (10%) on activated charcoal in 450 ml of methanol until the calculated mount of hydrogen has been consumed, the catalyst is filtered off, and the filtrate is freed from solvent, giving 37.56 g of 3-amino-2,5-dibromopyridine. STR12

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,15862-37-0, its application will become more common.

Reference:
Patent; Hoechst Aktiengesellschaft; US5445763; (1995); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 80194-70-3, 3-Chloro-5-(trifluoromethyl)picolinonitrile, 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, 80194-70-3, blongs to pyridine-derivatives compound. Formula: C7H2ClF3N2

Add 863g of absolute ethanol to a 3L four-necked round bottom flask and cool to 0 C to 5 C.HCl gas into 4 to 5 hours, weighed found that the quality of the system after the increase of 575g stopped by the HCl gas,Hydrogen chloride in ethanol was obtained. 110 g (0.533 mol) of 2-cyano-3-chloro-5-trifluoromethylpyridine was addedThe pyridine was dissolved in 15 g of ethanol, added dropwise to the above system at 30 C and stirred at 30 C3 hours. The system was warmed to 45 C and the reaction stirred at 45 C for 12 hours. The system was warmed to 75 C~ 80 , and the reaction was stirred at 75 ~ 80 for 4 hours. Concentrate the ethanol, and add 300mL of water,The mixture was stirred at 25 C to 30 C for 2 hours. The resulting system was extracted with 3 × 300 mL of dichloromethane,The combined organic layers were washed with 100 mL of saturated aqueous sodium bicarbonate until neutral. Concentrate diluted dichloromethaneThe residue was distilled under reduced pressure to collect the distillate from 120 C to 130 C and from 5 mmHg to 8 mmHg118.3 g of a colorless liquid was obtained in a yield of 87.6% and a GC purity of 99.58%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,80194-70-3, its application will become more common.

Reference:
Patent; Lianhua Technology Co., Ltd.; Zou Benli; Xu Tinghua; Yuan Li; Tan Wenping; Xie Siwei; (13 pag.)CN106905231; (2017); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 14432-12-3, 4-Amino-2-chloropyridine, 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, 14432-12-3, blongs to pyridine-derivatives compound. name: 4-Amino-2-chloropyridine

10.3 Synthesis of 2-chloro-3-iodo-pyridin-4-ylamine 2a* 2-Chloro-pyridin-4-ylamine 1a* (3.2 g, 25 mmol) and sodium acetate (4.1 g, 50 mmol) were stirred in acetic acid (20 mL). A solution of iodine monochloride (4.1 g, 25 mmol) in acetic acid (10 mL) was added and the reaction mixture was heated to 70 C for approximately three h (NB: reaction mixture became a solution at ?50 C, the brown colour faded and a precipitate formed as the reaction proceeded). The reaction mixture was cooled to room temperature, then poured onto water (700 mL), and extracted with AcOEt (2 x 750 mL). The organic phase was carefully washed with a saturated aqueous solution of sodium carbonate (500 mL) followed by a 10% solution of sodium thiosulfate (500 mL), dried over MgSO4 and concentrated in vacuo. The crude product was purified by column chromatography using 10% AcOEt in DCM to yield 2-chloro-3-iodo-pyridin-4-ylamine 2a* (2.6 g, 41 %). 1H NMR (400 MHz, CDCl3) delta (ppm): 7.88 (1 H, d, J = 5.5 Hz), 6.46 (1 H, d, J = 5.5 Hz), 4.96 (2 H, s).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,14432-12-3, its application will become more common.

Reference:
Patent; Max-Planck-Gesellschaft zur Foerderung der Wissenschaften e.V.; Ullrich, Axel (Prof. Dr.); Falcenberg, Mathias (Dr.); EP2818472; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 113118-81-3, 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 113118-81-3, name is 5-Bromonicotinaldehyde. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 5-bromonicotinaldehyde (LV) (2.0 g, 10.8 mmol, 1 eq) in MeOH (20 mL) was added NaB (2.4 g, 64.9 mmol, 6 eq) and the reaction mixture was stirred at room temperature for 3 h. The mixture was concentrated in vacuo and the residue was diluted in water (15 mL), the aqueous phase was extracted with DCM (10 mL x 3). The combined organic layers were dried over MgS04, filtered and concentrated in vacuo to afford (5-bromopyridin-3- yl)methanol (LXII) (1.8 g, 9.57 mmol, 90.0% yield) as a colorless oil. NMR (CDC13, 500 MHz) delta ppm 4.73 (s, 2H), 7.90 (s, 1H), 8.47 (s, 1H), 8.57 (s, 1H). ESIMS found for C6H6BrNO mlz 188.0 (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 113118-81-3, 5-Bromonicotinaldehyde.

Reference:
Patent; SAMUMED, LLC; KC, Sunil Kumar; WALLACE, David Mark; CAO, Jianguo; CHIRUTA, Chandramouli; HOOD, John; (280 pag.)WO2017/23986; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1480-65-5, 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. 1480-65-5, name is 5-Chloro-2-fluoropyridine, molecular formula is C5H3ClFN, 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.

To 2-methyl-4-(3-pipendin-4-ylpropoxy)benzoic acid hydrochloride (Preparation 22, 574 mg, 1.83 mmol) in DMSO (850 muL) was added 5-chloro-2-fluoropyndine (288 mg, 2.20 mmol), DBU (960 muL, 6 41 mmol) and H2O (6 drops) The resulting suspension was heated in a sealed tube in the microwave at 13O0C for 3 h The reaction mixture was diluted with H2O, acidified to pH 5 with 2M HCl and extracted with EtOAc (3x), then the combined organic extracts were washed with brine, before being dried (MgSO4). Filtration, removal of solvent under reduced pressure and purification by column chromatography (EtOAc-IH, 2 3 to 3:2) afforded the title compound: RT = 3.87 min; mlz (ES+) = 403.11 [M + H]+ (Method A).

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 1480-65-5, 5-Chloro-2-fluoropyridine.

Reference:
Patent; PROSIDION LIMITED; BERTRAM, Lisa, Sarah; FYFE, Matthew, Colin, Thor; JEEVARATNAM, Revathy, Perpetua; KEILY, John; WO2010/4344; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem