Category: pyridine-derivatives

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

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

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

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. 127561-18-6, name is 1-(6-(Trifluoromethyl)pyridin-2-yl)piperazine, the common compound, a new synthetic route is introduced below. Quality Control of 1-(6-(Trifluoromethyl)pyridin-2-yl)piperazine

A solution of 4-fluorophenyl /V-5-[(zPatent; CENTAURUS THERAPEUTICS; ROMERO, Donna, L.; BLITZER, Jeremy; (242 pag.)WO2019/140188; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 17282-40-5, Adding some certain compound to certain chemical reactions, such as: 17282-40-5, name is 1-(2-Ethoxy-2-oxoethyl)pyridin-1-ium bromide,molecular formula is C9H12BrNO2, 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 17282-40-5.

General procedure: Mixture of ethyl acetoacetate(1, 211 mg, 0.153 mmol), hydrazine (2, 81 mg, 0.153), 7-hydroxy-4-oxo-2-phenyl-4H-chromene-8-carbaldehyde (4a, 406 mg,0.153 mmol), 1-(2-ethoxy-2-oxoethyl)pyridinium ylide (4, 272mg, 0.153 mmol), 0.1 equivalents of trimethylamine (16 mg,0.015 mmol) in15 mL EtOH were refluxed in a pre-heated oilbath (80 C) under the blanket of nitrogen for 30 min till the completion of reaction (TLC, 20 % dicholromethane in hexanes; Rf = 0.3). The reaction mixture was diluted with dichloromethane (10 mL) and the organic solution was washed with water (20 mL) and brine (20 mL) and dried over anhydrousNa2SO4. Column chromatographic purification on silica gelwith increasing amount of dichlormethane in hexanes provided 8a as a free flowing solid in about 88 % yield. Analytical samples were obtained through from the recrystallization in EtOH.

According to the analysis of related databases, 17282-40-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Tangeti, Venkata Swamy; Vasundhara; Satyanarayana; Pavan Kumar, Kaja Srinivas; Asian Journal of Chemistry; vol. 29; 7; (2017); p. 1525 – 1532;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1263280-06-3, 5-Bromo-3,3-dimethyl-1H-pyrrolo[2,3-b]pyridin-2(3H)-one, 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: 5-Bromo-3,3-dimethyl-1H-pyrrolo[2,3-b]pyridin-2(3H)-one, blongs to pyridine-derivatives compound. Recommanded Product: 5-Bromo-3,3-dimethyl-1H-pyrrolo[2,3-b]pyridin-2(3H)-one

To a stirred solution of compound I (0.050 g, 0.207 mmol ) in propionitrile (4 ml) and DMF (1 ml) were added compound B( 0.047 g,0.207 mmol ),Pd(OAc)2( 0.004 g,0.0207 mmol ), P(o-tol)3 (0.011 g, 0.04 mmol )and DIPEA (0.053g, 0.4mm01 ) .The total reaction mass was purged with argon and heated at reflux temperature for 16 h. Reaction mass cooled to room temperature and concentrated under vacuum. Crude reaction mass was purified by column chromatography by eluting with 60% ethyl acetate in pet ether to afford the desired compound VT-02-00066 (0.017g). ? NMR (400 MHz, CDC13) 8.5 (s,lH ), 8.28(s,lH ), 7.6-7.63(d, J=1.2 Hz ,1H ),7.6(s,lH), 7.5(d, J= 8.0 Hz ,1H ) , 7.42 (d, J= 8.0Hz ,1H), 7.3 (m,2H), 6.85 (d, J= 2.0Hz ,1H ), 3.2 (d, J= 4.4Hz ,3H ), 1.44 (s,6H). MS(ESI): m/z 392(M+H)+

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1263280-06-3, 5-Bromo-3,3-dimethyl-1H-pyrrolo[2,3-b]pyridin-2(3H)-one, and friends who are interested can also refer to it.

Reference:
Patent; VITAS PHARMA RESEARCH PRIVATE LIMITED; RANGARAJAN, Radha; KUMAR, Rajinder; PRABHAKAR, B V; CHANDRASEKHAR, P; MALLIKARJUNA, P; BANERJEE, Ankita; WO2013/42035; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1083181-26-3, 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.1083181-26-3, name is 3-Iodo-1H-pyrrolo[3,2-b]pyridine, molecular formula is C7H5IN2, molecular weight is 244.03, as common compound, the synthetic route is as follows.

To a mixture of 3-iodo-1H-pyrrolo[3,2-b]pyridine (Intermediate 1), (350 mg) and potassium carbonate (791 mg) in DMF (8 mL) stirred at 0 C. under nitrogen was added 2-(4-(bromomethyl)-3-fluorophenyl)-6-methylpyridine hydrobromide (Intermediate 65), (620 mg). The reaction mixture was allowed to warm to rt and was stirred overnight. Water (50 mL) was added to the reaction mixture and the reaction mixture was extracted with EtOAc (100 mL). The organic phase was washed with brine (75 mL), dried (Na2SO4), filtered and evaporated under vacuum. The crude product was purified by column chromatography (silica) eluting with 28:72 EtOAc:hexanes to afford the title compound (580 mg) which was taken on as such. LCMS: m/z 444.11 [M+H]+.

The chemical industry reduces the impact on the environment during synthesis 1083181-26-3, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Payne, Andrew; Castro Pineiro, Jose Luis; Birch, Louise Michelle; Khan, Afzal; Braunton, Alan James; Kitulagoda, James Edward; Soejima, Motohiro; US2015/94328; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 5470-18-8, Adding some certain compound to certain chemical reactions, such as: 5470-18-8, name is 2-Chloro-3-nitropyridine,molecular formula is C5H3ClN2O2, 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 5470-18-8.

A 5 L round bottom flask fitted with a condenser, mechanical stirrer and a nitrogen inlet was charged with 152.3 g (0.96 mol) of 2-chloro-3-nitropyridine and 1.65 L of 1,2-dimethoxyethane. The solution was degassed by bubbling nitrgen through the solution for 10 min and 56.7 g (0.49 mol, 0.05 equiv) of tetrakis (tliphenylphosphine)-palladium (0) was added. The mixture was degassed for an additional 45 min during which time the catalyst dissolved leaving a clear dark red solution. A degassed solution of 180.3 g (1.48 mol, 1.54 equiv) of phenylboronic acid in 800 [ML] of absolute ethanol was added followed by 1.65 L of degassed 2M aqueous sodium carbonate solution. The cloudy mixture was heated to reflux, and refluxed for 1.5 h. While at reflux a yellow suspension formed. The suspension was cooled to ambient temperature, diluted with 1 L of ethyl acetate, and filtered through [CELITE THE] cake was washed with 2 L of ethyl acetate and the filtrate washed with water (2 x 3 L), saturated sodium bicarbonate solution [(1 X 3] L), and saturated sodium chloride solution (1 x 3 L). The organic layer was dried with magnesium sulfate, filtered and the filtrate concentrated. The residue was dissolved in 1.5 L of ether, washed with 2.5N [NAOH] (2 x 500 mL) and brine (500 mL). The solution was dried with magnesium sulfate, filtered through 400 g of silica and the cake washed with additional ethyl acetate. The filtrate was concentrated to an oil which was chromatographed [5 kg Silica Gel 60,70-230 mesh, hexanes/ethyl acetate 80: 20 (12 L), 75: 25 (8 L), 70: 30 (11 L) and 60: 40 (7 L) ]. The product fractions were concentrated yielding 188.0 g (97% yield) of the title compound 2-phenyl-3-nitropyridine, as a pale yellow oil: [IH] NMR [(CDCL3)] 8 7.39-7. 49 (m, [4H),] 753-7.95 (m, 2H), 8.12 (m, 1H) 8.84 (m, [1H).] MS [(EI)] [M/Z] 200. Anal. Calcd for [CLLH8N204] : C, 66.00 ; H, 4.03 ; N, 13.99. Found: C, 66.19 ; H, 4.09 ; N, 13.98.

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. 5470-18-8, 2-Chloro-3-nitropyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK & CO., INC.; WO2004/29024; (2004); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem