Category: pyridine-derivatives

Electric Literature of 884495-39-0, Adding some certain compound to certain chemical reactions, such as: 884495-39-0, name is 5-Bromo-2-methoxypyridin-3-amine,molecular formula is C6H7BrN2O, 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 884495-39-0.

2-(Methyloxy)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-pyridinamine To 5-bromo-2-(methyloxy)-3-pyridinamine (18.93 g, 93 mmol, available from Asymchem) in a 1 L round-bottom flask was added nitrogen-purged 1,4-Dioxane (500 mL) followed by 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi-1,3,2-dioxaborolane (47.4 g, 186 mmol), potassium acetate (27.5 g, 280 mmol) (0.402 g, 0.493 mmol) and PdCl2(dppf)-CH2Cl2 adduct (7.61 g, 9.32 mmol). The mixture was then stirred at 80 C. under nitrogen. The reaction mixture was allowed to cool then partitioned between ethyl acetate and water. The mixture was filtered through a celite pad and the aqueous layer extracted further with ethyl acetate (2*). The combined organics were washed with water, brine and dried over magnesium sulphate overnight. The residue was purified on 1.5 Kg Silica cartridge, eluting a 0-50% ethyl acetate/dichloromethane over 10 column volumes. The appropriate fractions were combined and evaporated to dryness. The residue was triturated with cyclohexane, the solid filtered off and dried in vacuo to leave the title compound as a light pink solid (1.1 g). LCMS (Method A) Rt 0.91 mins, MH+ 251A second crop was obtained from the above filtrate andafier drying gave a thrther portion of the title compound as alight pink solid (2.95 g).

According to the analysis of related databases, 884495-39-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Glaxo Group Limited; Hamblin, Julie Nicole; Jones, Paul Spencer; Keeling, Suzanne Elaine; Le, Joelle; Mitchell, Charlotte Jane; Parr, Nigel James; (136 pag.)US9326987; (2016); B2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1122-70-9, 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. 1122-70-9, name is 6-Methyl-2-vinylpyridine. A new synthetic method of this compound is introduced below.

Step F: Preparation of 1-[2-(6-Methyl-2-pyridyl)ethyl]-4-(benzofurazan-5-carbonyl)piperidine dihydrochloride 4-(Benzofurazan-5-carbonyl)piperidine hydrochloride (268 mg, 1 mmol), 2-methyl-6-vinylpyridine (286 mg, 2.4 mmol) and sodium acetate (187 mg, 2.3 mmol) in methanol/water (1:1, 4 ml) were heated under reflux for 3 hours, cooled and the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography on silica gel, eluding with CH2 Cl2 /CH3 OH/NH3 (Aq.); 96:4:0.4 to give a light brown solid. This was suspended in ethanol (2 ml) and ethanolic HCl (Ca. 1M, 2 ml) was added. The mixture was stirred at room temperature for 4 hours and the solid was collected and dried in vacuo to give the dihydrochloride as a light brown solid (260 mg. 61%), mp 228-231 C. deltaH(DMSO) 11.1 (1H, br s), 9.05 (1H, s), 8.25 (1H, br m), 8.19 (1H, d, J 9.5 Hz), 7.99 (1H, d, J 9.5 Hz), 7.65 (2H, br m), 4.0-3.1 (10H, m), 2.71 (3H, s), and 2.10 (4H, br m). Elemental analysis for C20 H22 N4 O2.2HCl: Calculated: C, 56.74; H, 5.71; N, 13.23%. Found: C, 56.34; H, 5.80; N, 13.13%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1122-70-9, its application will become more common.

Reference:
Patent; Merck & Co., Inc.; US5112824; (1992); A;,
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.73895-98-4, name is 6-Bromo-4-methylpyridin-2-amine, molecular formula is C6H7BrN2, molecular weight is 187.04, as common compound, the synthetic route is as follows.SDS of cas: 73895-98-4

This compound was forwarded to the next step without further purification. To a stirred solution of 6-amino-2-bromo-4-methylpyridine (45.2 g; 0.24 mol) in 100 ml water and 43 g concentrated sulphuric acid at ice-bath temperature was given a solution of sodium nitrite (13.2 g; 0.19 mol) in 20 ml water. After 2 hours the reaction mixture was warmed to 60 C. and stirred for further 60 minutes. After cooling, the mixture was extracted with 200 ml of dichloromethane. The solvent was removed in vacuo and 2-bromo-4-methyl-6-hydroxypyridine (20 g, 56%) was obtained as colourless crystals of melting point 152 C.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,73895-98-4, 6-Bromo-4-methylpyridin-2-amine, and friends who are interested can also refer to it.

Reference:
Patent; American Cyanamid Company; US5840654; (1998); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1122-54-9, 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.1122-54-9, name is 4-Acetylpyridine, molecular formula is C7H7NO, molecular weight is 121.14, as common compound, the synthetic route is as follows.

To a mixture of NaH (6.6 g, 165.2 mmol, 60%in mineral oil) in toluene (120 mL) was added dimethyl carbonate (11.2 g, 123.9 mmol) in toluene (40 mL) . Then 1- (pyridin-4-yl) ethanone (5.0 g, 41.3 mmol, 5) in toluene (40 mL) was added dropwise under N 2. The reaction mixture was stirred at 105 for 12 hours. After cooled to RT, the reaction was quenched with 200 mL (water) and HOAc (20 mL) and the mixture was stirred at RT for 20 minutes. Then the mixture was extracted with EtOAc (300 mL*3) . The combined organic layer was dried over Na 2SO 4, filtered and concentrated. The residue was purified by Prep-HPLC (water/acetonitrile = 10%to 90%) to give the title product (3.89 g, 53%, 6) as a brown solid. LC-MS: Rt = 1.20 min, [M+H] + = 180.

The chemical industry reduces the impact on the environment during synthesis 1122-54-9, I believe this compound will play a more active role in future production and life.

Reference:
Patent; SHANGHAI CHANGCHENGYIYAOKEJI COMPANY LIMITED; XU, Mingyan; (0 pag.)WO2020/1475; (2020); 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. 1215387-58-8, name is 5-Bromo-1H-pyrrolo[2,3-c]pyridine. A new synthetic method of this compound is introduced below., Application In Synthesis of 5-Bromo-1H-pyrrolo[2,3-c]pyridine

A stirred solution of 5-bromo-1H-pyrrolo[2,3-c]pyridine (2.22 g, 11.3 mmol) in DMF(30 ml) at ambient temperature was treated with potassium hydroxide (2.53 g, 45.1mmol). After 10 minutes, iodine (3.15 g, 12.4 mmol) was added and the resulting mixture was stirred for 2 hours. The mixture was diluted with water and extracted with EtOAc. The combined organic extracts were washed with brine, dried over Na2SO4 and concentrated in vacuo. The residue was triturated with water to afford the desiredproduct as an orange solid (3.39 g, 93%).LCMS (Method C): R 3.14 mm, mlz [M+H] 323/325.

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, 1215387-58-8, 5-Bromo-1H-pyrrolo[2,3-c]pyridine.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; HYND, George; TISSELLI, Patrizia; MACLEOD, Calum; MANN, Samuel, Edward; PANCHAL, Terry, Aaron; MONTANA, John, Gary; PRICE, Stephen, Colin; (74 pag.)WO2016/62790; (2016); 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. 13534-89-9, name is 2,3-Dibromopyridine, the common compound, a new synthetic route is introduced below. HPLC of Formula: C5H3Br2N

General procedure: A mixture of MeCN and MeOH (2:1, 15 ml) wasadded to a mixture of 2,3-dibromopyridine (1) (474 mg,2.0 mmol), arylboronic acid (2.1 mmol), K2CO3 (560 mg,4.0 mmol), PPh3 (52 mg, 10 mol %) and Pd(OAc)2 (23 mg,5 mol %) in a screw-cap vial. Reaction mixture was flushedwith argon, sealed, and stirred at 50C for 24 h in an oilbath. Then the reaction mixture was cooled to room temperature and filtered through Celite. Filtrate was concentratedunder reduced pressure, the residue was dissolved in CH2Cl2(20 ml), washed with water (3×10 ml) and dried overNa2SO4. Solvent was evaporated under reduced pressure,and the residue was purified by column chromatography on silica (hexane-EtOAc, 30:1) to provide pure pyridines 2a-j.

The synthetic route of 13534-89-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Shestakov, Aleksandr N.; Pankova, Alena S.; Kuznetsov, Mikhail A.; Chemistry of Heterocyclic Compounds; vol. 53; 10; (2017); p. 1103 – 1113; Khim. Geterotsikl. Soedin.; vol. 53; 10; (2017); p. 1103 – 1113,11;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 152684-30-5, 5-Bromo-2-methoxy-3-nitropyridine, 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: 152684-30-5, blongs to pyridine-derivatives compound. Recommanded Product: 152684-30-5

To a suspension of 5-bromo-2-methoxy-3-nitropyridine (0.4 g, 1.72 mmol) in EtOH (5 mL) and H2O (5 mL) were added iron powder (0.38 g, 6.87 mmol) and NH4Cl (0.39 g, 7.21 mmol). The reaction was heated to reflux and stirred further for 1 hour, and then concentrated in vacuo. The residue was diluted with EtOAc (10 mL) and the resulted mixture was filtered through a pad of CELITE. The filtrate was extracted with EtOAc (10 mL×3). The combined organic phases were washed with brine (10 mL), dried over anhydrous Na2SO4 and concentrated in vacuo to give the title compound as a yellow solid (0.30 g, 86%). [0301] MS (ESI, pos. ion) m/z: 203.0 [M+H]+; [0302] 1H NMR (400 MHz, CDCl3) delta (ppm): 3.92 (s, 3H), 4.86 (s, 2H), 7.03 (d, J=2.0 Hz, 1H), 7.41 (d, J=2.0 Hz, 1H).

The synthetic route of 152684-30-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; CALITOR SCIENCES, LLC; Xi, Ning; US2014/234254; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 626-64-2 ,Some common heterocyclic compound, 626-64-2, molecular formula is C5H5NO, 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.

Example 56Compound 68Compound 318 (Example 48; 98 mg, 0.34 mmol, 1 eq.) and PPh3 (138 mg, 0.53 mmol, 1 .5 eq.) were dissolved in dry THF (2 ml). Next DIAD (104 muIota, 0.53 mmol, 1 .5 eq.) and 4- hydroxypyridine (50 mg, 0.53 mmol, 1 .5 eq.) were added. The reaction mixture was stirred at RT for approximately 16 hrs, after which the solvent was removed and the crude mixture purified by flash column chromatography (silica, DCM/MeOH 1 :0 to 8:2) to afford compound 68 as a white foam (73 mg; 59%).

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. 626-64-2, Pyridin-4-ol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; UNIVERSITY OF DUNDEE; BESNARD, Jeremy; HOPKINS, Andrew Lee; GILBERT, Ian; RUDA, Gian Filippo; ABECASSIS, Keren; WO2012/160392; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 13466-38-1, 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. 13466-38-1, name is 5-Bromopyridin-2-ol, molecular formula is C5H4BrNO, 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.

termediate 17 ethyl trans-4-[(“5-bromopyridin-2-yl oxylcvclohexanecarboxylate To a mixture of 5-bromo-2-hydroxypyridine (11 g, 63.2 mmol), ethyl cis-4- hydroxycyclohexanecarboxylate (13.61 g, 79 mmol) and triphenylphosphine (20.73 g, 79 mmol) in THF (250 ml) at room temperature added diisopropyl azodicarboxylate (15.98 g, 79 mmol) dropwise, after that, the reaction mixture Was stirred overnight a at 55C for two days under N2. The reaction mixture was cooled to room temperature, then concentrated under vacuum. The residue was dissolved in 100 mL of ethyl acetate, then 100 mL hexane added. Stirred over night. The mixture was filtered and concentrated, the residue was purified by a silica gel column and eluted with ethyl acetate/hexane 0-50%. This resulted in ethyl trans-4- [(5-bromopyridin-2-yl)oxy]cyclohexanecarboxylate as a white solid. LC-MS (ES, m/z) C14H18BrN03: 327; Found: 328 [M+H]+.

According to the analysis of related databases, 13466-38-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME CORP.; DEVITA, Robert, J.; HE, Shuwen; LIU, Jian; CERNAK, Timothy, A.; KRIKORIAN, Arto, D.; YANG, Ginger XuQiang; WU, Zhicai; YU, Yang; SHEN, Dong-Ming; LAI, Zhong; HONG, Qingmei; NARGUND, Ravi, P.; WO2013/96093; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 175205-81-9, 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. 175205-81-9, name is 2-Bromo-4-(trifluoromethyl)pyridine. A new synthetic method of this compound is introduced below.

ter/-butyl (4-methoxybenzyl)(4-(4-(trifluoromethyl)pyridin-2-yl)thiazol-2-yl)carbamate was prepared from /er/-butyl (4-methoxybenzyl)(4-(4,4,5,5-tetramethyl-l ,3,2-dioxaborolan-2-yl)thiazol-2-yl)carbamate (0.558 g, 1.25 mmol), 2-bromo-4-(trifluoromethyl)pyridine (0.310 g, 1.37 mmol), K3PO4 (0.796 g, 3.75 mmol), Pd(dppf)Cl2 (0.91 g, 0.125 mmol) and DME/H2O (12 and 3 mF respectively); the reaction time was 3 h at 80 C. The product, purified by column chromatography (hexane:EtOAc; 1 :0 to 9: 1), was obtained as a colorless wax (0.350 g, 60 %). (0189) NMR (500 MHz, CDCl3) (ppm) 8.74 (d, J = 5.04 Hz, 1H), 8.25 (d, J = 1.57 Hz, 1H), 7.81 (s, 1H), (0190) 7.42 – 7.36 (m, 3H), 6.87 – 6.82 (m, 2H), 5.34 (s, 2H), 3.78 (s, 3H), 1.57 (s, 9H); (0191) 13C NMR (126 MHz, CDCl3) (ppm) 161.7, 159.1, 154.4, 150.3, 148.3, 139.2, 130.1, 129.6, 124.2 (q, ^C-F = 272.6 Hz), 122.1, 117.7 (d, 7 = 3.64 Hz), 116.6, 114.3, 113.9, 83.9, 55.4, 50.1, 28.4; (0192) 19F NMR (471 MHz, CDCl3) (ppm) -64.96; (0193) HRMS calcd for C22H23F3N3O3S [M+H]+ 466.1407, found 466.1409.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,175205-81-9, its application will become more common.

Reference:
Patent; MASARYKOVA UNIVERZITA; PARUCH, Kamil; CARBAIN, Benoit; HAVEL, Stepan; VSIANSKY, Vit; NIKULENKOV, Fedor; KREJCI, Lumir; (133 pag.)WO2019/201867; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem