Tag: M.W:100-200

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.100367-39-3, name is 4-Bromo-2-methoxypyridine, molecular formula is C6H6BrNO, molecular weight is 188.0219, as common compound, the synthetic route is as follows.Recommanded Product: 4-Bromo-2-methoxypyridine

To a resealable reaction pressure vessel under nitrogen was added 1.0 equiv of 55 (266 mg, 0.665 mmol), Pd(PPh3)4 (38 mg, 0.033 mmol, 5 mol %), K2C03 (184 mg, 1.33 mmol, 2.0 equiv), 2-methoxy-4-bromopyridine (137 mg, 0.732 mmol, 1.1 equiv), dioxane (20 mL) and water (2 mL). The mixture was degassed through bubbling nitrogen for 40 min and heated at 110 C overnight. After cooling to room temperature, water (20 mL) was added and the organic product was extracted using EtOAc (3 x 30 mL). The combined organic layers were dried over MgS04, filtered through Celite and the solvent removed in vacuo. The residual was purified by flash chromatography to provide 160 mg (63%) of 58 as colorless oil. 1H NMR (300 MHz, CDC13) delta 1.42 (br s, 9H), 1.49-1.63 (m, 2H), 1.86-1.98 (m, 3H), 2.00-2.07 (m, 1H), 2.96-3.01 (m, 1H), 3.92 (s, 3H), 4.30 (s, 1H), 4.42 (br s, 1H), 6.81 (dd, J = 5.7, 2.4 Hz, 1H), 7.25 (d, J= 2.2 Hz, 1H), 8.22 (t, J= 1.9 Hz, 1H), 8.53 (d, J= 5.7 Hz, 1H), 8.56 (d, J= 2.0 Hz, 1H), 9.00 (d, J = 2.0 Hz, 1H); 13C NMR (CDC13) delta 28.3 (3 C), 28.8, 29.9, 40.2, 45.8, 55.9, 61.8, 79.7, 107.2, 108.6, 132.9, 134.7, 140.9, 146.2, 149.1, 151.1, 155.0, 156.7 166.5; MS (ESI) m/z 382.7 (M+H)+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,100367-39-3, 4-Bromo-2-methoxypyridine, and friends who are interested can also refer to it.

Reference:
Patent; RESEARCH TRIANGLE INSTITUTE; CARROLL, Frank Ivy; ONDACHI, Pauline Wanjiku; WO2012/24615; (2012); A1;,
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.60832-72-6, name is Oxazolo[4,5-b]pyridin-2(3H)-one, molecular formula is C6H4N2O2, molecular weight is 136.1082, as common compound, the synthetic route is as follows.Safety of Oxazolo[4,5-b]pyridin-2(3H)-one

To a solution of 3/+oxazolo[4,5-6]pyridin-2-one (13.6 g, 100 mmol) in acetonitrile (600 mL) and acetic acid (120 mL) was added N-bromosuccinimide (21.4 g, 120 mmol). The mixture was stirred at room temperature for 4 hr and the reaction was quenched with Na2S205 solution. After evaporation, the residue was partitioned between ethyl acetate and water. The organic layer was washed with 2N NaOH solution, brine, and dried over Na2S04. The crude product was purified on a silica gel column to provide e-bromo-SAfoxazoloK.S-bJpyridin^-one (11.5 g, 55% yield).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,60832-72-6, Oxazolo[4,5-b]pyridin-2(3H)-one, and friends who are interested can also refer to it.

Reference:
Patent; PFIZER INC.; WO2006/21886; (2006); 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. 183208-35-7, name is 5-Bromo-1H-pyrrolo[2,3-b]pyridine. A new synthetic method of this compound is introduced below., Recommanded Product: 183208-35-7

Compound G, 5-bromo-1-(triisopropylsilyl-1H-pyrrolo[2,3-b]pyridine, may be prepared as follows. To a mixture of 5-bromo-1H-pyrrolo[2,3-b]pyridine (15.4 g) in tetrahydrofuran (250 mL) was added 1 M lithium hexamethyldisilazide in tetrahydrofuran (86 mL), and after 10 minutes, TIPS-Cl (triisopropylchlorosilane) (18.2 mL) was added. The mixture was stirred at room temperature for 24 hours. The reaction was diluted with ether, and the resulting solution was washed twice with water. The extracts were dried (Na2SO4), filtered, and concentrated. The crude product was chromatographed on silica gel with 10% ethyl acetate/hexanes to provide the product (Compound G).

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, 183208-35-7, 5-Bromo-1H-pyrrolo[2,3-b]pyridine.

Reference:
Patent; ACERTA PHARMA B.V.; HAMDY, Ahmed; ROTHBAUM, Wayne; IZUMI, Raquel; LANNUTTI, Brian; COVEY, Todd; ULRICH, Roger; JOHNSON, Dave; BARF, Tjeerd; KAPTEIN, Allard; (732 pag.)WO2016/24230; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 26218-80-4, Methyl 6-methoxynicotinate, 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, name: Methyl 6-methoxynicotinate, blongs to pyridine-derivatives compound. name: Methyl 6-methoxynicotinate

To a solution of methyl 6-methoxynicotinate (1.00 g, 5.98 mmol) in 20 mL of THF at 0 C under an atmosphere of nitrogen was added lithium aluminum hydride (1.0 M in THF, 9.0 mL, 9.0 mmol) dropwise. After 30 min, the reaction was warmed to rt, and after 30 mill, the reaction was recooled to 0 C, diluted with diethyl ether, and treated with water (0.34 mL), 15% aqueous sodium hydroxide (0.34 mL), and additional water (1.02 mL). The mixture was dried over magnesium sulfate and warmed to rt. After 15 min, the mixture was filtered through celite and concentrated in vacuo to provide (6-methoxypyridin-3-yl)methanol that gave a proton NMR spectra consistent with theory.

The synthetic route of 26218-80-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; KUDUK, Scott, D.; GILBERT, Kevin, F.; WO2011/159554; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1072-97-5 , The common heterocyclic compound, 1072-97-5, name is 5-Bromopyridin-2-amine, molecular formula is C5H5BrN2, 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.

5-Bromo-2-aminopyridine (5.19 g, 30 mmol) was dissolved in 100 mL of anhydrous dichloromethane.20 ml of triethylamine was added. In ice bath conditions,Slowly add acetyl chloride (2.54 ml) to the above solution, after the addition is completed,The ice bath was removed and allowed to warm to room temperature overnight. After the reaction,Dilute with dichloromethane,Washed (30ml × 3), washed with saturated NaHCO3 solution (30ml × 3),The mixture was washed with saturated NaCl (30 mL) and dried over anhydrous Na2SO.Column chromatography to obtain a white solid5.65 g, yield 88%.

The synthetic route of 1072-97-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Xi’an Jiaotong University; Zhang Jie; Pan Xiaoyan; Liang Liyuan; Lu Wen; Wang Sicen; He Langchong; Si Ru; Wang Jin; (15 pag.)CN109796439; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 89-00-9, Pyridine-2,3-dicarboxylic acid, 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, Safety of Pyridine-2,3-dicarboxylic acid, blongs to pyridine-derivatives compound. Safety of Pyridine-2,3-dicarboxylic acid

Synthesis of complex III was similar to that of II except that BaCl2 (0.105 g, 0.5 mmol) was used instead of FeCl2*4H2O (0.1268 g, 1 mmol). The pH was adjusted into 6, the mixture keep under autogenous pressure in 120C for 78 h, and then slowly cooled to room temperature at a rate of 5C/h. Then white crystals suitable for X-ray diffraction were separated and washed with water, which were stable in air and insoluble in water and common white solvents. The yield was 58% based on Ba.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,89-00-9, Pyridine-2,3-dicarboxylic acid, and friends who are interested can also refer to it.

Reference:
Article; Huang; Shi; Liu; Xiao; Yin; Russian Journal of Coordination Chemistry; vol. 41; 5; (2015); p. 325 – 333; Koord. Khim.; vol. 41; 5; (2015); p. 325 – 333,9;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 38186-88-8, 2-Chloro-5-fluoronicotinic acid, 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, 38186-88-8, blongs to pyridine-derivatives compound. Application In Synthesis of 2-Chloro-5-fluoronicotinic acid

Example 77; [0228] (a) Methyl 2-chloro-5-fluoronicotinate. To a mixture of 2- chloro-5-fluoronicotinic acid (6.66 g, 37.9 mmol) and K2CO3 (15.7 g, 1 14 mmol) in acetone (125 mL) was added iodomethane (2.60 mL, 41.7 mmol) dropwise with stirring at room temperature under nitrogen atmosphere. The reaction mixture was stirred at 35C for 18 hours and was filtered over a plug of Celite. The filtrate was evaporated under reduced pressure to give the title compound. MS (ESI, pos. ion) m/z: 190 (M+l).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,38186-88-8, its application will become more common.

Reference:
Patent; AMGEN INC.; WO2008/76425; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 76439-45-7 , The common heterocyclic compound, 76439-45-7, name is 3-Chloro-4-nitropyridine N-oxide, molecular formula is C5H3ClN2O3, 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. Preparation of 3-Ethylamino-4-nitro-pyridine-1-oxide [0215] Anhydrous K2CO3 (19 g, 144.5 mmol) is suspended in a solution of 3-chloro-4-nitro-pyridine-1-oxide (10 g, 57.8 mmol) in anhydrous acetonitrle (100 mL). Excess diethyl amine (2.0 M) in THF is added to the above suspension with ice-bath cooling. After complete addition of ethylamine, the reaction mixture is allowed to warm to room temperature and stir overnight. The reaction mixture is filtered to remove K2CO3 and the filtrate is evaporated under reduced pressure to remove volatile solvents. The organic residue is subjected to chromatography eluting with 30% EtOAc-hexanes to afford 3-ethylamino-4-nitro-pyridine-1-oxide as an orange solid (8.2 g) ; 1H NMR (300 MHz, CDCl3): 6 8.0 1 (d, J=7.5 Hz, 1H), 7.91(s, 1H), 7.8 (brs, NH), 7.44 (d, J=7.2 Hz, 1H) , 3.30 (t, J=7.2 Hz, 2H), 1.39 (t, J=7.2 Hz, 3H), m/z 184 [M+1]

The synthetic route of 76439-45-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Neurogen Corporation; US2004/14780; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 106689-41-2 , The common heterocyclic compound, 106689-41-2, name is 4-Hydrazinylpyridin-2(1H)-one, molecular formula is C5H7N3O, 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.

4-(2-4-methoxycyclohexylidene)hydrazinyl)pyridine-2(1H)-one [0342] 4-Hydrazinylpyridin-2(1H)-one (2.07 g, 16.5 mmol) was suspended in 4-methoxycyclohexanone (2.33 g, 18.2 mmol) solution in absolute ethanol (100 mL). After being heated to reflux for 2 hours, the reaction mixture was concentrated to half of its original volume. The resulting precipitates were filtered and dried to give 3.02 g (77.0%) colorless solid. 1HNMR (300 MHz, DMSO-d6) delta 10.50 (s, 1H), 9.28 (s, 1H), 7.07 (d, 1H, J=7.2 Hz), 6.01 (d, 1H, J=5.7 Hz), 5.67 (d, 1H, J=2.1 Hz), 3.45 (m, 1H), 3.28 (s, 3H), 2.35 (m, 2H), 2.20 (m, 2H), 1.86 (m, 2H), 1.62 (m, 2H)

The synthetic route of 106689-41-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF MICHIGAN; Wang, Shaomeng; Ran, Xu; Zhao, Yujun; Yang, Chao-Yie; Liu, Liu; Bai, Longchuan; McEachern, Donna; Stuckey, Jeanne; Meagher, Jennifer Lynn; Sun, Duxin; Li, Xiaoqin; Zhou, Bing; Karatas, Hacer; Luo, Ruijuan; Chinnaiyan, Arul; Asangani, Irfan A.; US2014/256706; (2014); A1;,
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. 128071-98-7, name is 4-Bromo-2-fluoropyridine, molecular formula is C5H3BrFN, 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: 4-Bromo-2-fluoropyridine

To a solution of 4-[[4-nitro-3-(trifluoromethyl)phenyl]amino]cyclohexan-l-ol (15 g, 49 mmol) in N-dimethylformamide (50 mL) was added sodium hydride (5.9 g, 246 mmol) The mixture was stirred for 30 minutes at 0 C. To this was added 4-bromo-2-fluoropyridine (8.7 g, 49 mmol). The resulting solution was stirred for 2 hours at 65 C. The reaction was then quenched by the addition of water. The resulting solution was extracted with ethyl acetate and the organic layers were combined and dried over anhydrous sodium sulfate before concentration under vacuum. The residue was applied onto a silica gel column and eluted with ethyl acetate/petroleum ether (1 :20?1 :5). Concentration of the product containing fractions provided 15.3 g (67%) of 4-nitro- V-[4-[(4-bromopyridin-2- yl)oxy]cyclohexyl]-3-(trifluoromethyl)aniline as a yellow solid; NMR (300 MHz, DMSO): delta 8.08 – 8.05 (m, 2H), 7.52 – 7.49 (m, 1H), 7.21 – 7.09 (m, 3H), 6.90 – 6.86 (m, 1H), 5.05 – 4.91 (m, 1H), 3.61 – 3.51 (m, 1H), 2.10 – 2.08 (m, 4H), 1.66 – 1.54 (m, 2H), 1.45 – 1.33 (m, 2H).

With the rapid development of chemical substances, we look forward to future research findings about 128071-98-7.

Reference:
Patent; MERIAL INC.; LONG, Alan; WILKINSON, Douglas, Edward; (224 pag.)WO2016/118638; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem