Day: September 3, 2021

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

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

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. 70201-42-2, name is 3,5-Dibromoisonicotinaldehyde, the common compound, a new synthetic route is introduced below. Quality Control of 3,5-Dibromoisonicotinaldehyde

To a solution of N-benzyloxycarbonyl-a-phosphono-glycine trimethyl ester (29.7 g, 89.7 mmol) in anhydrous DCM (500 mL) was added diazabicycloundec-7-ene (0.1 M solution in DCM, 14.6 mL, 97.9 mmol) dropwise. The reaction mixture was stirred for about 20 minutes at room temperature then a solution of 3,5-dibromo-pyridine-4-carbaldehyde (21.5 g, 81.6 mmol) in DCM (300 mL) was added dropwise and the resulting reaction mixture was stirred at room temperature for about 2 hours. The solvent was removed in vacuo and the resulting semi-solid taken up in EtOAc (500 mL) and washed with IN aqueous HCl (3 x 150 mL). The organic phase was separated, dried over sodium sulfate, and the solvent removed in vacuo. The resulting semi-solid was triturated using a 2:1 mixture of heptane-ethyl ether to provide 2-benzyloxycarbonyla»zirzo-3-(3,5-dibromo-pyridirz-4-yl)-acrylic acid methyl ester as an off-white powder (32.4 g, 69.1 mmol) ; ¹H NMR (d6-DMSO, 400 MHz): 8 9.44 (1H, bs), 8.72 (2H, s), 7.30-7.41 (5H, m), 6.59 (lH, s), 5.05 (2H, s), and 3.74 (3H, s) ; RP-HPLC (Table 1, Method n) Rt 4.18 min (major isomer); 111/Z: (M + H)(at) 471.

The synthetic route of 70201-42-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ABBOTT LABORATORIES; WO2005/110410; (2005); A2;,
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

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

Related Products of 849020-87-7 ,Some common heterocyclic compound, 849020-87-7, molecular formula is C7H4F3NO3, 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.

Diethyl chlorophosphate (0.186 ml, 1.285 mmol) was added to a stirring solution of 6-hydroxy-4-(trifluoromethyl)nicotinic acid (0.266 g, 1.285 mmol) in pyridine (3 ml) at room temperature. After stirring for lh the solution of activated acid was added to a stirring solution of 4-(3,4-dimethylpiperazin-1-yl)-6-fluoro-3′- (mo holinomethyl)-[l, -biphenyl]-3-amine (0.128 g, 0.321 mmol) also in pyridine (3 ml) at room temperature. The reaction was heated to 75 C overnight. LCMS indicated the presence of the desired product along with the excess nicotinic acid. The reaction was concentrated onto celite and purified by RP flash on the Biotage [5-95% MeCN/water] to afford 135 mg of crude product that was not of sufficient purity by NMR and LCMS. The mixture was loaded onto celite and purified by silica gel chromatography [1-25% MeOH/DCM + 1% NH40H] to afford the title compound (106 mg, 53.4 % yield) as a colorless solid after lyophilization. 11H NMR (500 MHz, DMSO-d6) delta 9.52 (s, 1H), 7.94 (s, 1H), 7.75 (d, J=8.44 Hz, 1H), 7.29-7.47 (m, 4H), 7.06 (d, J=12.47 Hz, 1H), 6.81 (s, 1H), 3.58 (t, J=4.40 Hz, 4H), 3.53 (s, 2H), 2.99- 3.09 (m, 2H), 2.80-2.87 (m, 1H), 2.74-2.80 (m, 1H), 2.32-2.46 (m, 6H), 2.23-2.27 (m, 1H), 0.99 (d, J=6.24 Hz, 3H); LCMS [M+H]+ 574 g/mol.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,849020-87-7, its application will become more common.

Reference:
Patent; ONTARIO INSTITUTE FOR CANCER RESEARCH (OICR); AL-AWAR, Rima; ZEPEDA-VELAZQUEZ, Carlos Armando; PODA, Gennady; ISAAC, Methvin; UEHLING, David; WILSON, Brian; JOSEPH, Babu; LIU, Yong; SUBRAMANIAN, Pandiaraju; MAMAI, Ahmed; PRAKESCH, Michael; STILLE, Julia Kathleen; (1053 pag.)WO2017/147700; (2017); A1;,
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

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. 1136-52-3, name is (2,2,8-Trimethyl-4H-[1,3]dioxino[4,5-c]pyridin-5-yl)methanol, molecular formula is C11H15NO3, 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. Computed Properties of C11H15NO3

General procedure: A mixture of alpha4,3-O-isopropylidene pyridoxine, the respective saccharideand molecular sieves (4 A) was stirred under argon atmospherein dry solvent (5 mL) at rt for 1 h before it was cooled to the respectivetemperature T. The promoter was added and the reaction mixture allowedto reach rt overnight. The mixture was diluted with dichloromethane(10 mL) and filtered through a pad of celite. Afterwards,the filtrate was washed with Na2S2O3 (10% in water, 30 mL) and theaqueous phase was extracted with dichloromethane (3 × 40 mL). Thecombined organic layers were washed with distilled water (1×50 mL),brine (1 × 50 mL) and dried over Na2SO4. The solvent was evaporatedunder reduced pressure and the crude product subjected to columnchromatography using SiO2 (pentane/ethyl acetate 1/1 to 1/4, gradientelution) followed by C18 (methanol, isocratic) to afford the glucoside.

With the rapid development of chemical substances, we look forward to future research findings about 1136-52-3.

Reference:
Article; Bachmann, Thomas; Rychlik, Michael; Carbohydrate Research; vol. 489; (2020);,
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: 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