Category: pyridine-derivatives

Related Products of 157402-44-3, The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 157402-44-3, name is 6-Phenylpicolinaldehyde. This compound has unique chemical properties. The synthetic route is as follows.

To a vigorously-stirred solution of 6-phenyl-2-pyridine aldehyde (0.50 g, 2.73 mmol) in 30 ml_ of anhydrous Et2O under N2, was added a solution of benzylmagnesium chloride (3 ml_ of 1 M solution in Et2O, 3.0 mmol) at ambient temperature. After 12 h, the reaction was quenched with 5 ml_ saturated aqueous ammonium chloride. This solution was extracted with 3 x 10 ml_ EtOAc. The organic fractions were pooled, dried over Na2SO4 and concentrated. After removing the volatiles in vacuo, the resultant yellow oil was chromatographed on silica with 10% EtOAc/hexanes. Clean fractions were combined and the volatiles were removed to provide 0.31 g of the alcohol intermediate as a yellow oil (41 %).

According to the analysis of related databases, 157402-44-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; EXXONMOBIL CHEMICAL PATENTS INC.; WO2008/85659; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 5470-17-7 , The common heterocyclic compound, 5470-17-7, name is 3-Bromo-2-chloro-5-nitropyridine, molecular formula is C5H2BrClN2O2, 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.

Step 1: 2-(3-bromo-5-nitropyridin-2-yloxy)-N, N-dimethylethanamine (Intermediatell).To a stirred solution of S-bromo-l-chloro-S-nitropyridine (2.5 g, 10.53 mmol) and 2-(dimethylamino) ethanol (1.877 g, 21.06 mmol) in DMF (10 mL) was added portion wise potassium carbonate (2.91 g, 21.06 mmol) and the mixture was stirred at 60 0C for 2- 3 hrs. Reaction mixture was cooled to RT, diluted with ethyl acetate (50-7OmI), washed with water and then brine, organic layer was collected, dried over sodium sulfate and concentrated in vacuo to give crude 2-(3-bromo-5-nitropyridin-2-yloxy)-N, N- dimethylethanamine (2.70 g, 88 %) as brown liquid. The crude material was taken for next step without further purification. MS (ES+): 292 for C9H12BrN3O3

The synthetic route of 5470-17-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2009/147431; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1480-64-4, The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 1480-64-4, name is 3-Chloro-2-fluoropyridine. This compound has unique chemical properties. The synthetic route is as follows.

3-Chloro-2-fluoropyridine (5.00 g, 37.25 mmol, 1 eq.) and benzylamine (5.75 mL, 52.15 mmol, 1.4 eq.) were addedto cesium carbonate (18.21 g, 55.88 mmol, 1.5 eq.) in dimethyl sulfoxide (25 mL) and the reaction mixture wasstirred at 105 C for 7 h. After cooling to 25 C water (25 mL) was added dropwise using an ice bath to maintain thetemperature below 30C. The reaction mixture was transferred to a separation funnel. Then water (15 mL) andethyl acetate (40 mL) were added and the phases were separated. The aqueous phase was extracted with ethylacetate (2 x 50 mL). The combined organic phases were washed with water (4 x 50 mL) and brine (50 mL). Dryingover magnesium sulfate, removal of the solvent and purification by flash chromatography (2 to 3% ethyl acetate inheptanes) gave the N-benzyl-3-chloropyridin-2-amine as a white solid (6.56 g, 81%). Rf = 0.25 (5% ethyl acetate inheptanes).1H NMR (400 MHz, CDCl3): = 1H NMR (400 MHz, CDCl3): = 4.71 (d, J = 5.5 Hz, 2 H), 5.28 (br. s, 1 H), 6.57 (dd, J =7.8, 5.0 Hz, 1 H), 7.27 – 7.32 (m, 1 H), 7.33 – 7.42 (m, 4 H), 7.46 -7.51 (obs. m, 1 H), 8.07 (dd, J = 4.9, 1.6 Hz, 1 H).13C NMR (101 MHz, CDCl3): = 45.5, 113.1, 115.4, 127.3, 127.7, 128.6, 136.1, 139.3, 146.0, 153.9.LC/MS (m/z): [M + H]+ calculated for C12H12ClN2+, 219.1 ; found, 218.7

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 1480-64-4, 3-Chloro-2-fluoropyridine.

Reference:
Article; De Gasparo, Raoul; Lustenberger, Philipp; Mathes, Christian; Schlama, Thierry; Veitch, Gemma E.; Le Paih, Jacques J. M.; Synlett; vol. 26; 2; (2015); p. 197 – 200;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 5350-93-6, 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.5350-93-6, name is 6-Chloropyridin-3-amine, molecular formula is C5H5ClN2, molecular weight is 128.56, as common compound, the synthetic route is as follows.

A solution of 5-amino-2-chIoropyridine (30.94 g, 236 mmol) and di-tert-butyldicarbonate (65.36 g, 299 mmol) in 1 ,4-dioxane (300 ml.) was stirred at reflux for 20 hours. Additional di- tert-butyldicarbonate (8.30 g, 38 mmol) was added and the reaction was stirred at reflux for 7 hours. The reaction was cooled to room temperature and poured into water. The Jayers were separated and the aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with brine, dried over magnesium sulfate, and solvent was removed at reduced pressure to give a brown oil. The oil was triturated with diethyl ether and filtered to give tert-butyl 6-chloropyridin-3-ylcarbamate as a tan solid. (49.84 g, 92% yield). 1H NMR (CDCI3) delta 8.24 (m, 1 H)1 7.96 (m, 1 H), 7.27 (m, 1 H), 6.65 (br s, 1 H), 1.51 (s, 9H).

The chemical industry reduces the impact on the environment during synthesis 5350-93-6, I believe this compound will play a more active role in future production and life.

Reference:
Patent; PHARMACIA & UPJOHN COMPANY LLC; WO2006/126083; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1335210-23-5, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 1335210-23-5 as follows.

Examples 9 and 10 Preparation of Compounds 9 and 1Theta (2S,5R,13aS)-N-((R)-H4-fluoroph^ octahydro-2,5-methanopyrido[ 1 ‘,2′:4,5]pyrazino[2, 1 -b][ 1 ,3]oxazepine- 10-carboxamide 9 and (2R,5S,13aR)-N-((R)-l-(4-fj.uorophenyl)ethyl)-8-hydroxy-7,9-dioxo- 2,3,4,5 J,9,13,13a-octahydro-2,5-methanopyrido[r,2’:4,5]pyrazino[2, b] [ 1 ,3]oxazepine- 10-carboxamide 10 Step 1 l-(2,2-dimethoxyethyl)-5-methoxy-6-(methoxycarbonyl)-4-oxo-l ,4- dihydropyridine-3-carboxylic acid (1-A, 0.500 g, 1.59 mmol), was suspended in acetomtrile (6 rnL) and treated with N,N-diisopropylethylamine (DIPEA) (0.550 mL, 3.17 nifflol), (R)-l-(4-fluoropbenyi)ethanamine (0.242 rng, 1.74 mmol) and HATXJ (0.661 g, 1.74 mmol). The reaction mixture was stirred for 2 hours and partitioned between ethyl acetate and water. The organic layer was separated and washed with HCl ( 10% aq), sodium bicarbonate (1 M aq), dried over sodium sulfate, filtered and concentrated to afford crude (R)-methyl l -(2,2-dimethoxyethyl)-5-(l -(4- fiuorophenyl)ethylcarbamoyl)-3-methoxy-4-oxo-l ,4-dihydropyridine-2-carboxylate which was used without purification in the next step: LCMS-ESI+ (m/z): [M+H] ; calculated for C”.< ; i ^ X -()··: 437.17; found: 437.1. These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1335210-23-5, its application will become more common. Reference:
Patent; GILEAD SCIENCES, INC.; JIN, Haolun; LAZERWITH, Scott, E.; MARTIN, Teresa, Alejandra, Trejo; BACON, Elizabeth, M.; COTTELL, Jeromy, J.; CAI, Zhenhong, R.; PYUN, Hyung-Jung; MORGANELLI, Philip, Anthony; JI, Mingzhe; TAYLOR, James, G.; CHEN, Xiaowu; MISH, Michael, R.; DESAI, Manoj, C.; WO2014/100323; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 5470-70-2, 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.5470-70-2, name is Methyl 6-methylnicotinate, molecular formula is C8H9NO2, molecular weight is 151.16, as common compound, the synthetic route is as follows.

[01 10j To a solution of methyl 6-methylnicotinate (0.5 g, 3.31 mmol) in carbon tetrachloride (15 mL) was added N-bromosuccinimide (0.647 g, 3.63 mmol) followed by azobisisobutyronitrile (0.054 g, 0.33 mmol). The reaction mixture was heated at 75 C for 18 h. The reaction mixture was diluted with dichloromethane, washed with water, dried over anhydrous sodium sulfate, filtered and concentrated. The crude was purified by silica gel column chromatography, using 50% ethyl acetate in hexane to afford methyl 6- (bromomethyl)nicotinate (0.28 g, 37% yield) as a brownish solid. Calculated M+H: 229.97; Found M+H: 230.01.

Statistics shows that 5470-70-2 is playing an increasingly important role. we look forward to future research findings about Methyl 6-methylnicotinate.

Reference:
Patent; MNEMOSYNE PHARMACEUTICALS, INC.; ANDERSON, David R.; VOLKMANN, Robert A.; WO2015/48503; (2015); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 133081-24-0, Adding some certain compound to certain chemical reactions, such as: 133081-24-0, name is 6-Hydrazinylnicotinic acid,molecular formula is C6H7N3O2, 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 133081-24-0.

A solution of DOTA tri-t-butyl ester (225 mg, 0.393 mmol), HOBt (50 mg, 0.33 mmol), and EDC (62 mg, 0.32 mmol) in 50:50 dichloromethane:acetonitrile (2.0 mL) was stirred at ambient temperatures under nitrogen for 5 minutes, and treated with 6-hydrazinictoic acid (50 mg, 0.32 mmol). The solution was stirred for 60 hours and concentrated under reduced pressure. The residue was purified by HPLC on a Phenomenex Luna Cl 8 column (21.2 x 250 mm) using a 0.9%/min gradient of 9 to 36% acetonitrile containing 0.1% TFA at a flow rate of 20 niL/min. The main product peak eluting at 32.9 minutes was lyophilized to give the title compound as an off-white solid (3.0 mg, 1.0%). MS (ESI): 708.4 (60, M+H).

According to the analysis of related databases, 133081-24-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BRISTOL-MYERS SQUIBB PHARMA COMPANY; WO2007/5491; (2007); 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. 5470-70-2, name is Methyl 6-methylnicotinate, molecular formula is C8H9NO2, 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. Product Details of 5470-70-2

250mL single-neck flask was added methyl 6-methylpyridine-3-carboxylate (10g, 66.15mmol) and 1,4-dioxane (100mL), was added under stirring selenium dioxide (14.7g, 132mmol), nitrogen heated to 85 under the protection of the reaction overnight. Cooling to room temperature, filtered, and the solvent was removed by rotary evaporation, the crude product was purified by silica gel column chromatography (petroleum ether / ethyl acetate (v / v) = 1/1), give a pale yellow solid 1.6g, Yield: 15percent.

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

Reference:
Patent; Guangdong East Sunshine Pharmaceutical Co., Ltd.; Wang, Xiaojun; Yang, Xinye; Zhou, Pingjian; Yang, Chuanwen; Lin, Jihua; Xiong, Shaohui; Zhang, Yingjun; Xiao, Ying; Wang, Hui; Cao, Shengtian; Wu, Fangyuan; Ouyang, Luo; (74 pag.)CN105524053; (2016); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 116632-24-7, 2-Amino-4,6-dichloropyridine, 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, category: pyridine-derivatives, blongs to pyridine-derivatives compound. category: pyridine-derivatives

A mixture of 4,6-dichloropyridin-2-amine (2.0 g, 12.3 mmol), ethynylbenzene (2.51 g, 24.5 mmol), copper(I) iodide (234 mg, 1.23 mmol), Dichlorobis(triphenylphosphine)- palladium(II) (1.0 g, 1.23 mmol) and triethylamine (4.3 ml, 31 mmol) is stirred under argon atmosphere in ACN (20 ml) with THF (10 ml) for 6 h at 90C. The mixture is diluted with water and extracted with EtOAc. The combined organic layers are dried over MgS04, concentrated in vacuo and the product purified by NP chromatography. Yield: 1.2 g (43%). HPLC-MS: M+H=229; tR=l .96 min (*Method_2).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,116632-24-7, 2-Amino-4,6-dichloropyridine, and friends who are interested can also refer to it.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; REISER, Ulrich; BADER, Gerd; SPEVAK, Walter; STEFFEN, Andreas; PARKES, Alastair L.; WO2013/127729; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 2002-04-2, 5-(Pyridin-4-yl)-1,3,4-thiadiazol-2-amine, 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, 2002-04-2, blongs to pyridine-derivatives compound. name: 5-(Pyridin-4-yl)-1,3,4-thiadiazol-2-amine

A solution of (i?)-3-methoxy-4-(l-phenyl-2-((triisopropylsilyl)oxy)ethoxy)benzoic acid (0.1.0 g, 2.2 mmol, 1 eq.), 5-(4-pyridyl)-l,3,4-thiadiazol-2-yl amine (0.467g, 2.6 mmol, 1.2 eq.), HATU (1.35 g, 3.5 mmol, 1.5 eq.) and diisopropylethylamine (480 mu^, 2.75 mmol, 1.2 eq.) in NMP (10 mL) was stirred at 70 C for 16 hours. The cooled reaction mixture was added to water (100 mL) and the crude product filtered and partitioned between dichloromethane (100 mL) and water (15 mL). The layers were separated and the aqueous extracted with a mixture of dichloromethane (100 mL) and methanol (10 mL). The combined extracts were dried with magnesium sulfate, evaporated in vacuo and purified by silica gel column chromatography using a 20 – 100 % ethyl acetate in iso- exane gradient to afford (R)-3 -methoxy-4-(l -phenyl-2-((triisopropylsilyl)oxy)ethoxy)-N-(5-(pyridin-4-yl)- l,3,4-thiadiazol-2-yl)benzamide as a white solid (0.784 g, 60% yield). NMR (400 MHz, DMSO) 13.16 (IH, s), 8.79 (2H, dd, J=1.6, 4.5 Hz), 7.99 (2H, dd, J=1.6, 4.4 Hz), 7.84 (IH, d, J=2.0 Hz), 7.68 (IH, dd, J=2.1, 8.6 Hz), 7.52 – 7.48 (2H, m), 7.40 (2H, dd, J=7.6, 7.6 Hz), 7.37 – 7.32 (IH, m), 7.09 (IH, d, J=8.9 Hz), 5.62 (IH, dd, J=4.5, 6.5 Hz), 4.14 (IH, dd, J=6.8, 10.6 Hz), 4.00 (IH, dd, J=4.5, 10.8 Hz), 3.97 (3H, s), 1.15 – 1.08 (3H, m), 1.07 – 1.02 (18H, m).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,2002-04-2, its application will become more common.

Reference:
Patent; GENKYOTEX SA; MACHIN, Peter; SHARPE, Andrew; LOCK, Christopher James; CHAMBERS, Mark S; HODGES, Alastair; ALLEN, Vivienne; ELLARD, John M; (189 pag.)WO2016/98005; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem