Month: September 2021

Adding a certain compound to certain chemical reactions, such as: 717843-48-6, 3-Bromo-6-methylpicolinonitrile, 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, HPLC of Formula: C7H5BrN2, blongs to pyridine-derivatives compound. HPLC of Formula: C7H5BrN2

(3) the 2 – bromo -6 – methyl -2 – cyano pyridine (25g, 127mmol) dissolved in the 1L in concentrated hydrochloric acid (HCl), mixture in 110 C stirring reaction under the condition of 2 days; removing the solvent to obtain crude product; the obtained crude product is dissolved in water, and addingNaHCO3, then filtered; the filtrate is ethyl acetate extraction, Na2SO4drying and vacuum concentrated to get the crude product 3 – bromo -6 – methyl -2 – picolinic acid; two product adds up the yield of 69.3%, about 19g.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,717843-48-6, 3-Bromo-6-methylpicolinonitrile, and friends who are interested can also refer to it.

Reference:
Patent; Suzhou Jianxiong Vocational and Technical College; Gu, Zhun; Wang, Yang; Jin, Chen; (7 pag.)CN106045902; (2016); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 58539-77-8, 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. 58539-77-8, name is 3-(Chloromethyl)-2-methylpyridine hydrochloride. A new synthetic method of this compound is introduced below.

A mixture of the compound of Example 42 (0.20 g, 0.57 [MMOL),] cesium carbonate (2.0 g, 5.7 [MMOL)] and 3-chloromethyl-2-methyl-pyridine hydrochloride (0.16 g, 0.91 [MMOL)] in a 2: 1 THF/DMF mixture was heated at [80C] for 15 hours. The cooled mixture was filtered and concentrated, and then water (30 mL) was added and the mixture extracted with ethyl acetate (3 x 30 mL). The combined organic layers were washed with brine, dried [(MGS04),] filtered and concentrated to a foam (0.31 [G).] The residue was purified by flash chromatography using a 30% to 70% ethyl acetate/hexanes eluant to afford 122 mg (47%) of the title compound as an oil. Mass spectrum: (m/e) 458 (M++1, +ion).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,58539-77-8, its application will become more common.

Reference:
Patent; PFIZER PRODUCTS INC.; WO2004/5229; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 14482-51-0, 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.14482-51-0, name is 2-Bromo-3,5-dichloropyridine, molecular formula is C5H2BrCl2N, molecular weight is 226.89, as common compound, the synthetic route is as follows.

NMP (7 mL) was added to a round bottom, placed under nitrogen and cooled to 00C. NaH (1.16 g, 29.1 mmol) was added portionwise followed by the addition of methyl cyanoacetate (1.31 ml, 14.5 mmol) (in 3 mL of NMP) dropwise. After stirring for 30 minutes at 00C, 2- bromo-3,5-dichloropyridine (3.0 g, 13.2 mmol) was added and the reaction was heated to 1300C for 5 hours. The reaction was allowed to cool, poured into ice and extracted twice with ethyl acetate. The ethyl acetate was combined, dried over MgSO4, filtered and concentrated. The amorphous material was crystallized from methanol to afford the desired compound (700 mg, 2.86 mmol, 21.6 % yield) as light brown needles.

Statistics shows that 14482-51-0 is playing an increasingly important role. we look forward to future research findings about 2-Bromo-3,5-dichloropyridine.

Reference:
Patent; ARRAY BIOPHARMA INC.; COOK, Adam; HUNT, Kevin, W.; DELISLE, Robert Kirk; ROMOFF, Todd; CLARK, Christopher, T.; KIM, Ganghyeok; CORRETTE, Christopher, P.; DOHERTY, George, A.; BURGESS, Laurence, E.; WO2010/75200; (2010); 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

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