Pyridine-derivatives

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.156772-60-0, name is 2,5-Dibromo-3-fluoropyridine, molecular formula is C5H2Br2FN, molecular weight is 254.88, as common compound, the synthetic route is as follows.Product Details of 156772-60-0

To a solution of 2,5-dibromo-3-fluoropyridine (2.077 g, 8.149 mmol) in toluene (35 mL) cooled to -78 C, was added BuLi (2.7 M, 3.169 mL, 8.556 mmol). The mixture was stirred 5 min at -78 C, then dimethylacetamide (1.035 g, 1.1 mL, 11.88 mmol) was added. The cooling bath was removed and the resulting mixture was stirred at 25 C for 30 min. The mixture was quenched with saturated aqueous solution of NH4CI (30 mL) and the resulting mixture was extracted with CH2CI2 (3 x 30 mL). The combined organic extracts were dried over MgSCL, filtered, and the solvent was evaporated in vacuo. The residue was purified by flash column chromatography (hexane :EtO Ac; 1 :0 to 20: 1 to 15: 1 to 10: 1). The product was obtained as a white solid (1.24 g, 70 %). (0348) NMR (500 MHz, Chloroform-d) (ppm) 8.56 (dd, / = 1.8, 1.1 Hz, 1H), 7.73 (dd, / = 9.7, 1.8 Hz, 1H), 2.68 (d, / = 1.0 Hz, 3H); (0349) 13C NMR (126 MHz, Chloroform-d) d (ppm) 197.0 (d, J = 4.5 Hz), 157.9 (d, J = 280.5 Hz), 146.1 (d, J = 4.7 Hz), 140.5 (d, / = 5.4 Hz), 128.7 (d, / = 22.5 Hz), 124.6 (d, / = 3.6 Hz), 28.0; (0350) 19L NMR (471 MHz, Chloroform-d) fit ppm) -116.90.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,156772-60-0, 2,5-Dibromo-3-fluoropyridine, and friends who are interested can also refer to it.

Reference:
Patent; MASARYKOVA UNIVERZITA; PARUCH, Kamil; CARBAIN, Benoit; HAVEL, Stepan; DAMBORSKY, Jiri; BREZOVSKY, Jan; DANIEL, Lukas; SISAKOVA, Alexandra; NIKULENKOV, Fedor; KREJCI, Lumir; (190 pag.)WO2019/201865; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1209459-88-0, 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 1209459-88-0, name is 4-Bromo-N-methylpicolinamide. This compound has unique chemical properties. The synthetic route is as follows.

Add 4.71g of 4-amino-3-fluorophenol, 4.13g of sodium hydroxide, 32.11g of potassium iodide, 22.78g of triethylbenzylammonium chloride, 500ml of water to the reaction flask, and heat to 30 C to stir and dissolve. When the temperature reaches At 70 C, 21.61 g of compound III was added dropwise, and the reaction was stirred for 2 h. After completion of the reaction, the mixture was cooled, washed with a 2% aqueous sodium hydroxide solution, and the mixture was separated. The organic layer was recrystallized from ethanol to give compound IV 25.48 g, product yield 97.5%, purity 99.96%.

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 1209459-88-0, 4-Bromo-N-methylpicolinamide.

Reference:
Patent; Shandong Luoxin Pharmaceutical Group Hengxin Pharmaceutical Co., Ltd.; Liu Zhenteng; Hou Junkai; Fan Xuezhen; Yang Taotao; (6 pag.)CN108329260; (2018); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 137129-98-7, 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. 137129-98-7, name is 6-Chloro-2-methylnicotinic acid, molecular formula is C7H6ClNO2, 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.

HATU (425 mg, 1.12 mmol) was added to a solution of 6-chloro-2-methyl-3-pyridinecarboxylic acid (commercially available, e.g. from Anichem, or may be prepared according to known methods) (160 mg, 0.93 mmol) in DMF (3 ml) and the mixture was treated with DIPEA (0.407 ml, 2.33 mmol). This mixture was stirred for ca. 10 min at ambient temperature. 3-Methyl-4-{[(3S)-3-methyl-1-piperazinyl]sulfonyl}benzonitrile (may be prepared as described in Description 11) (313 mg, 1.12 mmol) was added as a solution in DMF (2 ml) and stirring was continued for ca. 1 hour. The reaction mixture was partitioned between DCM and sat aq. NaHCO3 solution (20 ml each). The layers were separated and the aqueous was washed with further DCM (2×20 ml). The combined organic layers were dried (hydrophobic frit) and concentrated to leave a dark brown gum. Purification by silica chromatography (Biotage SP4, 25S cartridge), eluting with 12-100% ethyl acetate in isohexane, gave the title compound as a pale cream foam (376 mg).m/z (API-ES) 433/435 [M+H]+ (Cl isotopes)

According to the analysis of related databases, 137129-98-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Beswick, Paul John; Campbell, Alister; Cridland, Andrew; Gleave, Robert James; Heer, Jag Paul; Nicholson, Neville Hubert; Page, Lee William; Vile, Sadie; US2010/22555; (2010); A1;,
Pyridine – Wikipedia,
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. 1620-76-4, name is 4-Methylpicolinonitrile, the common compound, a new synthetic route is introduced below. HPLC of Formula: C7H6N2

Reference Example 55 4-Methyl-2-pyridinecarbaldehyde diisobutyl aluminium hydride in toluene (1.5 M, 43.5 ml, 65 mmol) was added dropwise to a solution of 2-cyano-4-methylpyridine (7.0 g, 59 mmol) in dichloromethane (180 ml) at -78 C, and the mixture was stirred at the same temperature for 2 hrs.. The reaction mixture was combined with concentrated hydrochloric acid (28 ml) and water (112 ml), and the water layer and the organic layer were separated.. The organic layer was extracted with 2 N hydrochloric acid.. The water layer was combined, neutralized with sodium hydrogen carbonate and extracted with diethyl ether.. The extract was washed with saturated brine and dried over anhydrous magnesium sulfate.. The solvent was evaporated to give the titled compound (2.7 g, 37 %).

The synthetic route of 1620-76-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Takeda Chemical Industries, Ltd.; EP1424336; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 15069-92-8, Adding some certain compound to certain chemical reactions, such as: 15069-92-8, name is 5-Hydroxypicolinic acid,molecular formula is C6H5NO3, 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 15069-92-8.

5-Hydroxypyridine-2-carboxylic acid (1.50 g) was dissolved in a mixed solvent of tetrahydrofuran (7.5 mL)/N,N-dimethylformamide (7.5 mL), tert-butylamine (1.7 mL), 1-hydroxybenzotriazole (2.20 g), triethylamine (4.5 mL) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (3.10 g) were successively added, and the mixture was stirred at room temperature for 24 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was separated and purified by silica gel column chromatography (hexane:ethyl acetate=33:67?0:100?ethyl acetate_methanol=95:5) to give the title compound (1.05 g) as an orange oil. 1H-NMR (CDCl3) delta: 1.49 (9H, s), 7.23 (1H, dd, J = 2.6 Hz, 8.6 Hz), 7.90-8.01 (2H, m), 8.17 (1H, d, J = 2.6 Hz), 8.57 (1H, br s)

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. 15069-92-8, 5-Hydroxypicolinic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Takeda Pharmaceutical Company Limited; EP2103620; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1678-53-1, 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.1678-53-1, name is 3-Methyl-4-nitropyridine, molecular formula is C6H6N2O2, molecular weight is 138.12, as common compound, the synthetic route is as follows.

To a solution of 250 mg (1.86 mmol) of furopyridine 71, 618 mg (4.47 mmol) of nitropicoline 35 in 8 mL of THF was added 4.47 mL (4.47 mmol) of a 1 M solution of TBAF and 732 mg (5.59 mmol) of Huenig’s base. The mixture was stirred at 60 C for 5 days at which point a slurry had formed. The mixture was cooled to room temperature, filtered, and the product washed with 5 mL of THF and dried under vacuum/N2 sweep overnight to give 350 mg (59%) of dimeric furopyridine 72 as a colorless solid: mp 228e229 C; 1 H NMR (500 MHz, CDCl3) d 3.25 (dd, 2H, J 15.8 and 8.1 Hz), 3.72 (dd, 2H, J 15.8 and 9.6 Hz), 5.88 (dd, 2H, J 9.6 and 8.1 Hz), 6.84 (d, 2H, J 5.6 Hz), 7.42 (s, 4H), 8.40 (m, 4H); 13C NMR (125 MHz, CDCl3) d 35.5, 84.8, 105.6, 123.4, 126.1, 141.0, 145.9, 150.2, 166.0. Anal. Calcd. For C20H16N2O2: C, 75.93; H, 5.10; N, 8.86. Found: C, 75.88; H, 5.07; N, 8.89.

The chemical industry reduces the impact on the environment during synthesis 1678-53-1, I believe this compound will play a more active role in future production and life.

Reference:
Article; Kuethe, Jeffrey T.; Tetrahedron; vol. 75; 34; (2019);,
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. 84249-14-9, name is 2-Amino-4-bromopyridine, molecular formula is C5H5BrN2, 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. COA of Formula: C5H5BrN2

Step 1: N-(4-bromopyridin-2-yl)cyclopropanecarboxamide To a stirring solution of 4-bromopyridin-2-amine (200 g, 1160 mmol) in DCM (2000 mL) and pyridine (183 g, 2310 mmol) was added cyclopropanecarbonyl chloride (157 mL, 1500 mmol) dropwise at 0 C. under a nitrogen atmosphere. The reaction mixture was allowed to stir at 0 C. for 12 h then the reaction mixture was allowed to warm to rt. The reaction mixture was washed with 1N HCl solution (3*500 mL) and brine (500 mL). The organic solution was dried over Na2SO4, filtered and concentrated to give N-(4-bromopyridin-2-yl)cyclopropanecarboxamide (224 g, 80% yield) as a white solid. LCMS (FA): m/z=241.0 (M+H).

With the rapid development of chemical substances, we look forward to future research findings about 84249-14-9.

Reference:
Patent; MILLENNIUM PHARMACEUTICALS, INC.; Bharathan, Indu T.; Blackburn, Chris; Ciavarri, Jeffrey P.; Chouitar, Jouhara; Cullis, Courtney A.; D’Amore, Natalie; Fleming, Paul E.; Gigstad, Kenneth M.; Gipson, Krista E.; Girard, Mario; Hu, Yongbo; Lee, Janice; Li, Gang; Rezaei, Mansoureh; Sintchak, Michael D.; Soucy, Francois; Stroud, Stephen G.; Vos, Tricia J.; Wong, Tzu-Tshin; Xu, He; Xu, Tianlin; Ye, Yingchun; US2015/225422; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 193537-14-3 , The common heterocyclic compound, 193537-14-3, name is Ethyl 6-Boc-2-amino-4,7-dihydro-5H-thieno[2,3-c]pyridine-3-carboxylate, molecular formula is C15H22N2O4S, 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 solution of 6-tert-butyl 3-ethyl 2-amino-4,7-dihydrothieno[2,3-c]pyridine-3,6(5H)-dicarboxy- late from Example 9A (1.23 kg, 3.77 mol) in DMF (10.3 L) was added formamidine acetate (588 g, 5.65 mol). The mixture was heated to 1000C overnight. The solvent was removed in vacuo. The residue was stirred with ethyl acetate (3 L) for 2 h. The precipitate was collected by suction filtration and rinsed with ethyl acetate. The solid was dried to yield 1.02 kg (88%) of the title compound.1H-NMR (400 MHz, DMSOd6): delta = 1.43 (s, 9H), 2.91-2.96 (m, 2H), 3.62 (t, 2H), 4.58 (s, 2H), 8.05 (s, IH), 12.38 (br. s, IH).LC/MS (method 4): R, = 2.03 min; MS (ESIpos): m/z = 308 [M+H]+.

The synthetic route of 193537-14-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER HEALTHCARE AG; WO2009/33581; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 173435-32-0 ,Some common heterocyclic compound, 173435-32-0, molecular formula is C6H7FN2, 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.

2-Fluoro-4-methylpyridin-3-amine (1.0 g, 7.93 mmol) and 2 , 5-dimethoxytetrahydrofuran (1.08 mL, 1.05 equiv. ) were suspended in 3 mL of acetic acid and refluxed for 2 hours. The reaction was cooled down to room temperature. The solvents were removed and the residue was purified by silica gel chromatography (EtOAc/hexanes = 1:8, Rf = 0.3) to afford 1.0 g (72%) oil. XH NMR (400 MHz, CDC13) delta 8.10 (dd, J=0.8, 5.1 Hz, 1H) , 7.17 (d, J=5.1 Hz, 1H) , 6.74 (td, J=2.1, 0.9 Hz, 2H) , 6.40 (t, J=2.1 Hz, 2H) , 2.26 (s, 3H) . 13C NMR (101 MHz, CDC13) delta 160.2, 157.8, 149.6, 149.5, 145.5, 145.4, 123.80, 123.76, 122.1, 109.8, 17.29, 17.25. HRMS (m/z) calcd for Ci0Hi0F 2 (M+H) 177.0828; found 177.0827. Richards, et al. (2008) Bioorg. & Med. Chem. Lett. 18:4325-27.

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. 173435-32-0, 2-Fluoro-4-methylpyridin-3-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; UNIVERSITY OF KANSAS; THE SCRIPPS RESEARCH INSTITUTE; AUBE, Jeffrey; BOHN, Laura; PRISINZANO, Thomas, Edward; SCHOENEN, Frank, John; FRANKOWSKI, Kevin, John; WO2013/40321; (2013); 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. 55279-29-3, name is 3-Aminoisonicotinaldehyde. This compound has unique chemical properties. The synthetic route is as follows. Application In Synthesis of 3-Aminoisonicotinaldehyde

tert-Butyl 4-({4-[(3-aminopyridin-4-yl)methyl]morpholin-2-yl}methyl)piperazine-1-carboxylate 3-Amino-pyridine-4-carbaldehyde (584 mg, 4.78 mmol) was dissolved in DCM (10 mL) and tert-butyl 4-(morpholin-2-ylmethyl)piperazine-1-carboxylate (1.50 g, 5.26 mmol) and NaBH(OAc)3 (1.11 g, 5.26 mmol) were added. The reaction mixture was heated in a microwave at 60 C. for 2.5 min, diluted with DCM (20 mL) and quenched with sat aq Na2CO3 (10 mL). The organic fraction was washed with sat aq NH4Cl (10 mL). The combined aq fractions were extracted with DCM (2*20 mL) and the combined organic fractions were dried (MgSO4) and concentrated in vacuo to give the crude title compound as a yellow gum (2.46 g). LCMS (ES+): 392.1 [MH]+.

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, 55279-29-3, 3-Aminoisonicotinaldehyde.

Reference:
Patent; PROXIMAGEN LIMITED; Carley, Allison; Simpson, Iain; US2014/275063; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem