Pyridine-derivatives

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. 1594-58-7, name is N-Hydroxynicotinimidamide, molecular formula is C6H7N3O, 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. Application In Synthesis of N-Hydroxynicotinimidamide

Add 0.05 mol (6.85 g) to a 250 mL three-necked flaskN-hydroxynicotinamide,100mL acetonitrile as solvent,0.055 mol (5.5 g) of triethylamine as an acid binding agent, and stirring, 0.05 mol (16.5 g) of 3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carbonyl chloride Diluted with 50 mL of ethyl acetate and added dropwise to the reaction flask.The reaction was carried out for 2 h after the completion of the dropwise addition.TLC monitoring until the reaction is complete,Add an appropriate amount of saturated sodium bicarbonate solution,Filtering,Made a brown solid,Rinse with methanol to obtain 18.1 g of a yellow solid.The yield was 96.02%.

With the rapid development of chemical substances, we look forward to future research findings about 1594-58-7.

Reference:
Patent; Qingdao University of Science and Technology; Wang Minghui; Xu Liangzhong; Liu Liancai; Sun Jianxin; Cui Huanqi; (7 pag.)CN109336879; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 60032-57-7, 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 60032-57-7, name is 2-Methylnicotinaldehyde. This compound has unique chemical properties. The synthetic route is as follows.

(b) methyl 2-Q -(hydroxy(2-methyipyridin-3-yl)mnethyi)bcnzofuran-5-yl)acctate: To asohLtion of methyl 2-(Z-bromobenzofuran-5-yi)acctate (0.35 g, 1.3 mmol) in dry THE (5 niL) wasadded i-PrMgCI-iithium chloride (1.3 M solution in THF, 1.3 mL, 1.6 nnol) dropwise at 0 C andthe reaction mixture was stilTed for 30 mm maintaining the same temperature. ?To the reaction mixture was added a solution of 2-methylnicotinaldehyde (157 rng, 1.3 mniol) in dry TF1F (5 mL) and the reaction mixture was further stirred for 2 h at 0 C. The reaction mixture was quenched with saturated NH4C1 solution and the organic product was extracted with EtOAc. The organic layer was dried over anhydrous Na2SO4 and the solvent was removed under vacuum. The crudeproduct was purified by column chromatography (neutral alumina, eluent 5-10% MeOI-f in CH2C12) to afford the title compound (160 mg, yield 40%) as a yellow viscous liquid. ?H NMR (300 MHz, MeOH-d,) 6 ppm 8.36 – 8.34 (dd, J= 4.9 Hz, 1.6 Hz, IH), 8.01 – 7.97 (dd, J= 7.9 Hz, 1.5 Hz, 1H), 7.447.43 (d,J 1.3 Ffz, 1Ff), 7.37-7.30 (in, 2Ff), 7.18 -7.14 (dd,J 8.4 Ffz, 1.6 Ffz, 1Ff), 6.56 (s, 1ff), 6.08 (s, 1Ff), 3.69 (s, 2Ff), 3.65 (s, 3Ff), 2.52 (s, 3Ff).

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 60032-57-7, 2-Methylnicotinaldehyde.

Reference:
Patent; TEMPERO PHARMACEUTICALS, INC.; BALOGLU, Erkan; GHOSH, Shomir; LOBERA, Mercedes; SCHMIDT, Darby, R.; WO2013/19626; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 5467-69-6, 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 5467-69-6, name is 6-Methoxy-2-methyl-3-nitropyridine. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of intermediate 74 (2 g, 0.012 mol) in H20/MEOH 1: 1 (40 mL), were added NH4CI (2.2 g, 3.5 eq. ) and Fe powder (2.3 g, 3.5 eq. ). The reaction mixture was stirred at 80C for 16 hr. Fe was then filtered and washed with MeOH. The MeOH was evaporated, H20 was added and the aqueous solution was extracted with EtOAc (3X50 mL). The combined organic extracts were dried over anh. NA2SO4, the solids were filtered and the solvent evaporated to dryness to give the title compound (1.35 g, 81 %) as a brown oil. NMR (‘H, CDCI3) : 8 6.9 (d, 1 H), 6.4 (d, 1 H), 3.8 (s, 3H), 2.33 (s, 3H).

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 5467-69-6, 6-Methoxy-2-methyl-3-nitropyridine.

Reference:
Patent; SB PHARMCO PUERTO RICO INC; NEUROCRINE BIOSCIENCES INC; GLAXO GROUP LIMITED; WO2004/62665; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 186593-43-1, 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.186593-43-1, name is 5-Amino-3-bromo-2-methylpyridine, molecular formula is C6H7BrN2, molecular weight is 187.0372, as common compound, the synthetic route is as follows.

Step 1: EDC (1.3 equiv.) was added to a solution of 5-bromo-6-methylpyridin-3-amine (1.05 equiv), 2-(2-cyanopropan-2-yl)isonicotinic acid (1.0 equiv), HOAt (1.3 equiv) in DMF (0.17 M). The mixture was stirred at ambient temperature 3 hrs. The reaction mixture was diluted with water and extracted with ethyl acetate. The combined extracts were washed sequentially with 1M aqueous sodium hydroxide and brine, dried over sodium sulfate, filtered, and concentrated. The crude was purified by ISCO(50% EtOAc/Heptane). Combined fractions still contained 17% 5-bromo-6-methylpyridin-3-amine. Add 2-(2-cyanopropan-2-yl)isonicotinic acid (0.3 equiv), EDC (0.3 equiv), HOAt (0.3 equiv) in DMF (0.17 M). After stirred at rt overnight, the reaction mixture was diluted with water and extracted with ethyl acetate. The combined extracts were washed sequentially with 1M aqueous sodium hydroxide and brine, dried over sodium sulfate, filtered, and concentrated to yield N-(5-bromo-6-methylpyridin-3-yl)-2-(2-cyanopropan-2-yl)isonicotinamide in 71% over three steps. LCMS (m/z) (M+H)=359.0, Rt=0.73 min.

Statistics shows that 186593-43-1 is playing an increasingly important role. we look forward to future research findings about 5-Amino-3-bromo-2-methylpyridine.

Reference:
Patent; NOVARTIS AG; Barsanti, Paul A.; Burger, Matthew; Lou, Yan; Nishiguchi, Gisele; Polyakov, Valery; Ramurthy, Savithri; Rico, Alice; Setti, Lina; Smith, Aaron; Taft, Benjamin; Tanner, Huw; DiPesa, Alan; Yusuff, Naeem; US2014/275003; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 246847-98-3, 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. 246847-98-3, name is 5-Chloro-3-fluoropyridin-2-amine. A new synthetic method of this compound is introduced below.

To concentrated sulfuric acid (100mL) cooled to -10 was added 2-amino-3-fluoro-5-chloropyridine (10 g, 68.2 mmol) with stirring. After dissolution, the mixture was continued to stir at -10 for 15min. Then 50 mL 30%hydrogen peroxide solution was added slowly, and the reaction temperature was maintained below 0. The mixture was warmed to room temperature and stirred for 72h, then poured into 500 mL 13%ice brine with stirring and extracetd with 200mL EA for three times. The combined organic extracts were washed with saturated sodium bicarbonate solution until the aqueous phase was alkaline, dried with anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by column chromatography to give the desired product 2-nitro-3-fluoro-5-chloropyridine (2.8g, 23.3%) .

At the same time, in my other blogs, there are other synthetic methods of this type of compound,246847-98-3, 5-Chloro-3-fluoropyridin-2-amine, and friends who are interested can also refer to it.

Reference:
Patent; FUJIAN HAIXI PHARMACEUTICALS CO., LTD; FENG, Yan; WANG, Ruyong; LI, Junqing; ZHENG, Jianjia; LIAN, Xin; GONG, Xuan; FU, Yueli; KANG, Xinshan; (144 pag.)WO2019/174601; (2019); 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. 588729-99-1, name is 3-Amino-5-bromo-2-chloropyridine. A new synthetic method of this compound is introduced below., Product Details of 588729-99-1

Step 1. 6-Bromo-thiazolo [5,4-b] pyridin-2-yl amine:(Intermediatel) In a 50ml RB flask, 5-bromo-2-chloropyridin-3-amine (3.11 g, 15 mmol) was taken in cone. HCl (30 mL) and sonicated well to give pale brown solution. To this potassium thiocyanate (2.187 g, 22.50 mmol) was added and the resulting mixture was heated at 1000C for 6hrs .The reaction mixture was changed to pale yellow suspension after 30 minutes of reflux. The reaction mixture was evaporated in vacuo; ice-cold water was added to the residue, sonicated well and neutralized with saturated sodium carbonate under cooling condition. The precipitated solid was sonicated well, filtered and dried under high vacuum afforded the product as off-white solid (2.5gm)MS (ES+): 231 Rw C6H4BrN3S1H NMR 5(DMSO-dfi): 5.85 (bs, 2H,NH2); 7.3 (s, lH,Aro); 7.65 (s, lH,Aro).

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, 588729-99-1, 3-Amino-5-bromo-2-chloropyridine.

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

Related Products of 5435-54-1, 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. 5435-54-1, name is 3-Nitropyridin-4-ol, molecular formula is C5H4N2O3, 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.

4-Hydroxy-3-nitropyridine (10 g, 71.38 mmol) was added to 100 ml of phosphorus oxychloride. The reaction mixture was refluxed for 1 hour and then concentrated under reduced pressure. The resulting residue was added to 500 ml of ice water and then neutralized with 2N sodium hydroxide solution. The reaction mixture was extracted with 300 ml of methylene chloride. The separated organic layer was dried on anhydrous magnesium sulfate and then concentrated under reduced pressure to give the titled compound (9.2 g, 92.0 %) as a pale yellow solid.[145] Rf (n-hexane/ethyl acetate = 2/1 , v/v) = 0.5[146] 1H-NMR (400MHz, CDCl ) delta 9.12(s,lH), 8.69(d,lH), 7.55(d,lH)

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 5435-54-1, 3-Nitropyridin-4-ol.

Reference:
Patent; YUHAN CORPORATION; WO2007/1139; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 153034-82-3 , The common heterocyclic compound, 153034-82-3, name is 2-Fluoro-4-iodonicotinaldehyde, molecular formula is C6H3FINO, 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.

[00343] (2-Fluoro-4-iodopyridin-3-yl)methanol F OH. To a solution of 2-fluoro-4- iodonicotinaldehyde (3.50 g, 13.94 mmol) in absolute EtOH (56 mL) was added sodium borohydride (0.264 g, 6.97 mmol) at room temperature. The reaction was stirred at room temperature for 1 h, followed by the slow addition of 1 M aqueous hydrochloric acid. The product was extracted with CH2CI2 (repeated four times), and the organic layers were combined, dried over sodium sulfate, filtered and concentrated to dryness. The aqueous phase was basified to pH 8-10 with 2 M aqueous sodium hydroxide and extracted with diethylether (repeated four times). Then the organic layers were combined, dried over sodium sulfate, filtered, combined with the previously obtained residue and concentrated to dryness under vacuum. The residue was used without any purification in the next step. LC/MS m/z 254[M+H]+.

The synthetic route of 153034-82-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CONSTELLATION PHARMACEUTICALS, INC.; ALBRECHT, Brian K.; AUDIA, James Edmund; COTE, Alexandre; GEHLING, Victor S.; HARMANGE, Jean-christophe; HEWITT, Michael C.; LEBLANC, Yves; NAVESCHUK, Christopher G.; TAYLOR, Alexander M.; VASWANI, Rishi G.; WO2012/75383; (2012); A2;,
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.1196073-28-5, name is Methyl 4,6-dichloro-2-methylnicotinate, molecular formula is C8H7Cl2NO2, molecular weight is 220.05, as common compound, the synthetic route is as follows.Quality Control of Methyl 4,6-dichloro-2-methylnicotinate

To a stirred suspension of sodium hydride (60% in mineral oil, 85 mg, 2.14 mmol) in DMF (4 mL) was added, dropwise, ethyleneglycol mono t-butyl ether (278 mg, 2.35 mmol). the reaction mixture was stirred for 25 min. A solution of 4,6-dichloro-2-methyl- nicotinic acid methylester (0.5g, 2.14 mmol) in DMF (1.5 mL) was added to the reaction mixture was stirred at RT overnight. The reaction mixture was quenched with water, extracted with EtOAc, the organic layer washed with water, brine, dried over Na2SO4 and volatiles removed. The residue was purified by column chromatography using 0-50% EtOAc/Hexanes to provide compound Villa (260 mg).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1196073-28-5, Methyl 4,6-dichloro-2-methylnicotinate, and friends who are interested can also refer to it.

Reference:
Patent; THRESHOLD PHARMACEUTICALS, INC.; WO2009/140553; (2009); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 60290-21-3, 4-Chloro-1H-pyrrolo[3,2-c]pyridine, 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, COA of Formula: C7H5ClN2, blongs to pyridine-derivatives compound. COA of Formula: C7H5ClN2

General procedure: To a solution of 4-chloro-lH-pyrrolo-[3,2-c]-pyridine [60290-21-3] (2.0 g, 13.1 mmol) dissolved in DMF (30.5 mL, 0.944 g/mL, 393.2 mmol) at 0C was added portionwise sodium hydride (1.1 g, 28.8 mmol). The reaction mixture was allowed to reach rt and stirred 45 min, after which it was re-cooled to 0C and l-bromobutane (2.1 mL, 1.27 g/mL, 19.7 mmol) was added dropwise. The mixture was then allowed to reach rt and stirred overnight. NaHC03 sat solution was added and the aqueous phase was extracted with EtOAc. The combined organic extracts were washed with water and brine, then dried over MgS04 and concentrated in vacuo. The crude residue was purified by column chromatography (silica gel; gradient Heptane/EtOAc from 100/0 to 50 /50) to yield 1-1 (2.7 g, 98.7%) as a yellow liquid

The synthetic route of 60290-21-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; BARTOLOME-NEBREDA, Jose Manuel; TRABANCO-SUAREZ, Andres, Avelino; TRESADERN, Gary John; MARTINEZ LAMENCA, Carolina; LEENAERTS, Joseph Elisabeth; OEHLRICH, Daniel; BUIJNSTERS, Peter Jacobus Johannes Antonius; VELTER, Adriana, Ingrid; VAN ROOSBROECK, Yves, Emiel, Maria; (171 pag.)WO2019/243535; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem