Tag: M.W:100-200

1990-90-5 , The common heterocyclic compound, 1990-90-5, name is 3-Methylpyridin-4-amine, molecular formula is C6H8N2, 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 2-(5-Chloro-2-fluoro-phenyl)-4-iodo-6,6-dimethyl-6,7-dihydro-5H- cyclopentapyrimidine (100 mg, 0.25 mmol), 3-Methyl-pyridin-4-ylamine (30 mg,0.27 mmol), Pd(OAc)2 (3 mg, 12.42 mumol) and itoc-BINAP (12 mg, 18.63 mumol) in dry dioxane (3 mL) was added Cs2CO3 (121 mg, 0.37 mmol). The mixture was heated for 48 h at 85C, cooled and evaporated. HPLC purification gave, after lyophilization, the desired product of formula (60) as the TFA salt, which was a white solid (6.4 mg)

The synthetic route of 1990-90-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TIBOTEC PHARMACEUTICALS LTD.; WO2006/35061; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

620-08-6, Adding a certain compound to certain chemical reactions, such as: 620-08-6, 4-Methoxypyridine, 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, 620-08-6, blongs to pyridine-derivatives compound.

General procedure: According to the raw material ratio of Table 1, a copper additive, elemental iodine, alkali, aryl ethyl ketone (IV), pyridine derivative (III), electron-deficient olefin (II) and organic solvent 1 ml were added to a 10 ml sealed tube, and the mixture was stirred and mixed uniformly. In Table 1, A is cuprous chloride; B is cuprous iodide; C is sodium carbonate; D is potassium carbonate; E is N-methylpyrrolidone; and F is N,N-dimethylformamide. After completion of the reaction according to the reaction conditions of Table 2, the reaction solution was transferred to a separatory funnel containing 10% sodium thiosulfate solution, and the aqueous phase was extracted three times with ethyl acetate. The mixture was dried, filtered, and the filtrate was added to a silica gel mixture, and the solvent was evaporated to dryness, and purified by silica gel column chromatography (eluent ethyl acetate and petroleum ether mixture) to obtain the corresponding C-3 arylformylpyridazine compound (I)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,620-08-6, its application will become more common.

Reference:
Patent; Guizhou Chinese Academy Of Sciences Natural Result Chemical Emphasis Experiment Shi (Guizhou Medical University Natural Result Chemical Emphasis Experiment Shi); Yang Yuzhu; Fang Youlai; Liu Xiaolan; He Lisheng; (14 pag.)CN110156776; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

1122-62-9 , The common heterocyclic compound, 1122-62-9, name is 1-(Pyridin-2-yl)ethanone, molecular formula is C7H7NO, 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-Bromoacetyl)pyridin-1-ium bromide (A): To a stuffed solution of 1-(pyridin-2- yl)ethan-1-one (2.0 g, 16.6 mmol) in Cd4 (60 ml), bromine (2.7 g, 16.60 mmol) was added dropwise. After complete addition the final reaction mixture was refluxed for 1 h. The precipitate was collected by filtration and washed 2-3 times with diethylether and dried to obtain compound A as a beige solid (2.94 g, 93%).

The synthetic route of 1122-62-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VYOME BIOSCIENCES PVT. LTD.; SENGUPTA, Shiladitya; GHOSH, Shamik; GHOSH, Sumana; SINHA, Mau; SADHASIVAM, Suresh; BHATTACHARYYA, Anamika; MAVUDURU, Siva Ganesh; TANDON, Nupur; KUMAR, Deepak; (149 pag.)WO2017/17631; (2017); A2;,
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.628-13-7, name is Pyridinehydrochloride, molecular formula is C5H6ClN, molecular weight is 115.56, as common compound, the synthetic route is as follows.628-13-7

2-Amino-4-chloro-5-cyanopyridine (200 mg, 1.30 mmol, Production example 215-3) was dissolved in ethoxyethanol (13.0 ml); 5-aminoindole-1-carboxylic acid phenylamide (408 mg, 1.62 mmol, Production example 201-2) and pyridine hydrochloride (315 mg, 2.73 mmol) were added thereto; and the reaction mixture was heated and stirred at 130 C for 4 hours. After cooling to room temperature, the reaction mixture was partitioned between a saturated aqueous solution of sodium hydrogencarbonate and ethyl acetate; the organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (Fuji Silysia NH, hexane: ethyl acetate = 2: 3, ethyl acetate, ethyl acetate: methanol = 95: 5 in this order). The pale yellow oil obtained was solidified with diethyl ether; the crystals were suspended with diethyl ether, filtered off, washed with diethyl ether, and dried to yield the title compound (171 mg, 0.464 mmol, 35.7%) as colorless crystals.1H-NMR Spectrum (DMSO-d6) delta (ppm) : 5.77 (1H, s), 6.40 (2H, brs), 6.74 (1H, d, J=3.6 Hz), 7.13 (1H, t, J=7.6 Hz), 7.17 (1H, dd, J=2.4, 8.8 Hz), 7.38 (2H, t, J=7.6 Hz), 7.46 (1H, d, J=2.4 Hz), 7.64 (2H, d, J=7.6 Hz), 8.04 (1H, s), 8.05 (1H, d, J=3.6 Hz), 8.20 (1H, d, J=8.8 Hz), 8.35 (1H, s), 10.04 (1H, s).

Statistics shows that 628-13-7 is playing an increasingly important role. we look forward to future research findings about Pyridinehydrochloride.

Reference:
Patent; Eisai Co., Ltd.; EP1522540; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

766-11-0, A common compound: 766-11-0, name is 5-Bromo-2-fluoropyridine,molecular formula is C5H3BrFN, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

Preparation of 3-Methyl-5-(4,4,5,5-tetramethyl-[1 ,3,2]dioxaborolan-2-yl)-1 H-pyrazolo[3,4-b]pyridine (79) 7475 76 77Step 1 :7475To a stirred solution of diisopropyl-amine (50 g, 0.5 mol) in dry THF (1000 mL) was added dropwise n- BuLi (200 mL, 0.5 mol) at -780C under N2 atmosphere. After the addition, the resulting mixture was allowed to warm up to O0C, maintained for 10 minutes and cooled to -780C again. A mixture of compound 74 (80 g, 0.455 mol) in THF (1000 mL) was added dropwise to the LDA solution at -780C under N2 atmosphere. After the addition, the reaction mixture was stirred at -780C for 30 minutes. Then formic acid ethyl ester (50 g, 0.68 mol) was added portionwise to the mixture at -780C. After 2 minutes, the resulting mixture was quenched with a solution of 10% citric acid in THF (400 mL) at -780C. The mixture was allowed to warmed up to room temperature and poured into H2O (500 mL), extracted with EtOAc (500 mL x 3). The combined organic layers were washed with brine (500 mL), dried over Na2SO4 and concentrated in vacuo to give compound 75 (92 g, 99%) as a yellow solid.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 766-11-0.

Reference:
Patent; PFIZER INC.; WO2009/16460; (2009); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 5470-70-2, Methyl 6-methylnicotinate, 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, 5470-70-2, blongs to pyridine-derivatives compound. 5470-70-2

To a solution of methyl 6-methylnicotinate (25 g, 0.16 mol) in ethyl ether (620 mL) under nitrogen was added dropwise sodium bis(2-methoxyethoxy)aluminium hydride (Red-Al.(R).) (65wt.percent in toluene, 110 mL, 0.37 mol) at room temperature. The mixture was then heated to reflux for 1.5 hr. After cooling, the reaction mixture was quenched with water (500 mL) at 0 0C and the aqueous layer was extracted with EtOAc. The combined organic layers were dried over anhydrous MgSO4, filtered, and concentrated. The residue was purified by silica gel column to afford the title compound.

With the rapid development of chemical substances, we look forward to future research findings about 5470-70-2.

Reference:
Patent; RENOVIS, INC.; WO2009/110985; (2009); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

55589-47-4, 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.55589-47-4, name is 3-Methylpicolinaldehyde, molecular formula is C7H7NO, molecular weight is 121.14, as common compound, the synthetic route is as follows.

To a solution of X4-012-3 (4.0 g, 21.5 mmol), L-proline (1.0 g, 8.7 mmol) and 3-methylpicolinaldehyde (3.4 g, 28.0 mmol) in MeOH (200.0 mL) was added aq. methanamine (6 mL, 40percent). The solution was stirred at room temperature overnight. The solvent was removed under reduced pressure and purified by column chromatography to give X4-012-4 (4.1 g, 59.6 percent yield) as an orange solid. The structure was confirmed by H-HNOESY. LCMS (Agilent LCMS 1200-6120, Column: Waters X-Bridge C18 (50 mm*4.6 mm*3.5 iim); Column Temperature: 40 ¡ãC; Flow Rate: 2.0 mL/min; Mobile Phase: from 90percent [(total 10 mM AcONH4) water/CH3CN = 9/1 (v/v)] and 10percent [(total 10 mM AcONH4) water/CH3CN = 1/9 (v/v)] to 10percent [(total 10 mM AcONH4) water/CH3CN = 9/1 (v/v)] and 90percent [(total 10 mM AcONH4) water/CH3CN = 1/9 (v/v)] over 1.6 mm, then held under this condition for 2.4 mm, finally changed to 90percent [(total 10 mM AcONH4) water/CH3CN = 9/1 (v/v)] and 10percent [(total 10 mM AcONH4) water/CH3CN = 1/9 (v/v)] over 0.1 mm and held under this condition for 0.7 mi. Purity: 74.83 percent. Rt = 1.49 mm; MS Calcd.: 320.1; MS Found: 321.2 [M + H], MS Found:353.3 [M+MeOH].

Statistics shows that 55589-47-4 is playing an increasingly important role. we look forward to future research findings about 3-Methylpicolinaldehyde.

Reference:
Patent; X4 PHARMACEUTICALS, INC.; BOURQUE, Elyse Marie Josee; SKERLJ, Renato; (279 pag.)WO2017/223229; (2017); 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. 5398-44-7, name is 2,6-Dichloroisonicotinic acid. A new synthetic method of this compound is introduced below., 5398-44-7

To a solution of 2,6-dichloroisonicotinic acid (2 g, 10.4 mmol) in toluene (50 mL) N,N dimethylformamide di-tert-butil acetal (15 mL, 62.5 mmol) was added under nitrogen atmosphere and mixture heated at 80 Ethyl acetate was added and organic layer was washed with water and brine, dried (MgSO4), filtered and concentrated to yield the title compound (2.34 g, 87%) as a solid.LRMS (m/z): 249 (M+1)+.1H NMR (400 MHz, CHLOROFORM-d) ppm 1.60 (s, 9 H) 7.74 (s, 2 H)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,5398-44-7, 2,6-Dichloroisonicotinic acid, and friends who are interested can also refer to it.

Reference:
Patent; Almirall, S.A.; Vidal Juan, Bernat; Forns Berenguel, Maria Pilar; Castillo Mcquade, Marcos; Erra Sola, Montserrat; Mir Cepeda, Marta; EP2441755; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Some common heterocyclic compound, 16063-70-0, molecular formula is C5H2Cl3N, 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.16063-70-0

400 g of sulfolane and 400 g of dimethylsulfoxide were weighed into a 1000 mL flask and dehydrated to a temperature of less than 0.05% at 200 C under a pressure of 0.07 MPa (negative pressure)96 g (1.66 mol) of cesium fluoride, 96 g (1.66 mol) of potassium fluoride, 120 g (0.67 mol) of trichloropyridine, 2 g of 18-crown ether and 3 g of potassium carbonate were weighed into a reaction flask at 120 C and heated to 200 C The product was collected in about 3 hours. 95 g (0.51 mol) of the product was obtained in 90% yield. The purity was 96.8% as determined by gas chromatography.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 16063-70-0.

Reference:
Patent; Weixun Chemical (Nanjing) Co., Ltd; Wang, Faqiang; (4 pag.)CN106008329; (2016); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

586-95-8, 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. 586-95-8, name is 4-Pyridinemethanol. This compound has unique chemical properties. The synthetic route is as follows.

General procedure: A solution of catalyst 1 (2 mol %, 0.01 mmol), acetophenone (1.0 mmol), benzyl alcohol (1.2 mmol), cesium carbonate (1.5 mmol), and xylene (3 mL) were stirred in a Schlenk tube in N2 atmosphere. The mixture was heated under reflux for 24 h and then cooled to room temperature. The resulting solution was directly purified by column chromatography with petroleum ether/ethyl acetate (10 : 1) as eluent to give the desired product.

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, 586-95-8, 4-Pyridinemethanol.

Reference:
Article; Yu; Wang; Wu; Wang; Russian Journal of General Chemistry; vol. 86; 1; (2016); p. 178 – 183; Zh. Obshch. Khim.;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem