Category: pyridine-derivatives

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 59020-10-9, name is 3-(Tributylstannyl)pyridine. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 59020-10-9

A stirred solution of 3-amino-5-bromo-benzotrifuoride (Apollo, England ; 1.12 g, 5 [MMOL)] and 3- (tri-n-butylstannyl) pyridine (Maybridge Chemical Co. Ltd., England ; 2.0 g, 5.4 [MMOL)] in xylene (30 mL) was purged with argon for 10 minutes at [20C.] Tetrakis (triphenylphosphine)- palladium (0) (1. 16 g, 1.0 [MMOL)] is then added and the resulting mixture is heated at [140C] for 36 hours under an argon atmosphere. The mixture is then cooled, treated with an aqueous solution of sodium hydroxide (100 mL of 0.1 M) and purged with air for 2 hours. The resulting mixture is then diluted with ethylacetate (200 mL) and filtered. The orgainic phase is then sequentially washed with water (2 x 80 mL) and saturated aqueous sodium chloride (1 x 80 mL), dried (MgSO4), filtered and the solvent is evaporated off under reduced pressure to yield the crude product which is purified by column chromatography (silica gel, eluent ethyl acetate) to afford the title compound as a brown [OIL. 1H-NMR] (400 MHz, [DMSO-D6,] [8)] : 5.73 (br s, 2H), 6.83 (dd, 1 H), 6.99 (d, 1 H), 7.04 (d, 1 H), 7.39 (dd, 1 H), 7.64 (d, [1 H),] 8.42 (m, 1 H) and 8. 53 (dd, [1 H).]

With the rapid development of chemical substances, we look forward to future research findings about 59020-10-9.

Reference:
Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2004/5281; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 55052-26-1, Adding some certain compound to certain chemical reactions, such as: 55052-26-1, name is 1H-Pyrrolo[2,3-b]pyridin-6-ol,molecular formula is C7H6N2O, 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 55052-26-1.

A mixture of 1H-pyrrolo[2,3-b]pyridin-6-ol (0.200 g, 1.49 mmol) and K2CO3 (1 g, 7.45 mmol) in acetone (30 mL) was stirred under N2 at room temperature for 1 h. MeI (0.166 g, 1.192 mmol) was added. The reaction mixture was stirred under N2 at 50 C. for 12 h and then filtered. The filtrate was concentrated to half its volume, diluted with water, and extracted with CH2Cl2. The organic layer was dried over anhydrous MgSO4, and evaporated to give a residue, which was purified on a column of silica gel eluting with EtOAc/hexane (1:4) to give 6-methoxy-1H-pyrrolo[2,3-b]pyridine (159 mg, 89%).

According to the analysis of related databases, 55052-26-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Hsieh, Hsing-Pang; Chao, Yu-Sheng; Liou, Jing-Ping; Chang, Jang-Yang; Tung, Yen-Shih; US2006/148801; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 59290-82-3, 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 59290-82-3, name is 3-Nitroisonicotinic acid. This compound has unique chemical properties. The synthetic route is as follows.

A mixture of 3-nitroisonicotinic acid (1.75 g, 10.1 mmol), l-amino-2-methylpropan-2-ol (968 ul, 10.1 mmol), 2-(lH-benzotriazole-l-yl)-l,l,3,3-tetramethyluronium tetrafluoroborate (4.86 g, 15.1 mmol) and triethylamine (4.9 ml, 35.3 mmol) in tetrahydrofurane (60 ml) was stirred over the week-end at rt. The reaction mixture was diluted with ethyl acetate, washed with water, with brine, dried with magnesium sulfate and concentrated. The crude product was purified by silica gel chromatography using a CH2Cl2/MeOH gradient as eluent, providing the title compound as off-white solid (255 mg, 11%).MS: M = 240.0 (M+H)+

According to the analysis of related databases, 59290-82-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; BLEICHER, Konrad; FLOHR, Alexander; GROEBKE ZBINDEN, Katrin; GRUBER, Felix; KOERNER, Matthias; KUHN, Bernd; PETERS, Jens-Uwe; RODRIGUEZ SARMIENTO, Rosa Maria; WO2011/154327; (2011); A1;,
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.58539-65-4, name is 2-Methylnicotinamide, molecular formula is C7H8N2O, molecular weight is 136.1512, as common compound, the synthetic route is as follows.HPLC of Formula: C7H8N2O

Example 5 7-(4-hydroxy-3,5-dimethylphenyl)-1,6-naphthyridin-5(6H)-one I chloride (1.90 mL, 21.8 mmol) was added to 2-methyl nicotinic acid (1.50 g, 10.9 mmol) in anhydrous dichloromethane (20 mL) with triethylamine (1.6 mL, 11.5 mmol) and the reaction mixture was kept at room temperature overnight before the solvent was removed. THF was added to the residue and ammonia gas was bubbled through for 2 h. The THF was removed and the residue was dissolved into methanol and water and the pH was adjusted to 10.0 with potassium carbonate. The mixture was concentrated. After column chromatography the desired amide was isolated (1.10 g, 73.8%). NaH (0.428 g, 10.7 mmol, 60% in mineral oil) was added to 4-hydroxy-3,5-dimethylbenzonitrile (1.50 g, 10 mmol) in anhydrous DMF (8 mL). Benzyl bromide (1.83 g, 10.7 mmol) was added and the reaction was kept at room temperature overnight. The reaction mixture was poured into water. The isolated solid was further washed with hexane to yield the desired ether building block (2.0 g, 84.3%). It was used in the next reaction without further purification. The above amide (0.65 g, 4.77 mmol) in anhydrous THF (15 mL) was added drop-wise to BuLi (7.5 mL, 1.60 M) at -20 C. The reaction mixture was kept at this temperature for 1 h and then the above ether building block (1.13 g, 4.77 mmol) in THF (20 mL) was added drop-wise at -20 C. and the reaction was stirred for 1.5 h. The reaction temperature was increased to room temperature and continued for a further 1 h. Water (20 mL) was added and the mixture was stirred for a while before the solvent was removed and the residue was purified by column chromatography to yield the desired intermediate (0.50 g, 29.4%). A 50 mL flask was charged with the above described intermediate (0.50 g, 0.0014 mol) and pyridine hydrogen chloride (2.4 g, 0.014 mol) and the mixture was heated to 180 C. for 1.5 h. The mixture was cooled and poured into methanol (4 mL), then filtered. The collected solid was further washed with ethyl acetate and dried to give 7-(4-hydroxy-3,5-dimethylphenyl)-1,6-naphthyridin-5(6H)-one (350 mg, 82.7%) as an HCl salt. Selected data: MS (ES) m/z: 266; MP >350 C.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,58539-65-4, 2-Methylnicotinamide, and friends who are interested can also refer to it.

Reference:
Patent; RVX Therapeutics Inc.; McLure, Kevin G.; Young, Peter Ronald; US2013/281397; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 63572-73-6, 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 63572-73-6, name is 5-Nitro-1H-pyrazolo[3,4-b]pyridine. This compound has unique chemical properties. The synthetic route is as follows.

5-Nitro–1H-pyrazolo[3,4-b]pyridine (prepared according to the procedure in Can. J. Chem. 1988, 66(3), 420) (133 mg, 0.81 mmol) was mixed with SnCI2 (1.0g) in EtOH/CH3Ph (4 mL/2mL) and heated at 70 0C for 3 hrs. The reaction was cooled to rt and concentrated to dryness. The residue was participated between 1.0 N NaOH (10 mL) and ethyl acetate (50 mL). The organic layer was washed with brine once, dried (MgSO4) and filtered. The filtrate was concentrated and the resulting crude was purified by prep. TLC using 10:2 CH2CI2/Methanol(2 N NH3). The title compound (15.0 mg) was isolated as a yellow solid.

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 63572-73-6, 5-Nitro-1H-pyrazolo[3,4-b]pyridine.

Reference:
Patent; SCHERING CORPORATION; WO2007/70398; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 17117-13-4, 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. 17117-13-4, name is 2-Bromo-4-ethoxypyridine. A new synthetic method of this compound is introduced below.

[00337] Sodium tert-butoxide (210 mg, 2.2 mmol), l-phenylimidazol-4-amine (Hydrochloride salt) (245 mg, 1.3 mmol), and 2-bromo-4-ethoxy-pyridine (126 mg, 0.6 mmol) were weighed into a microwave vial. The mixture was diluted with 1,4- dioxane (5 mL) and degassed with nitrogen for 10 minutes. 0.1 Equivalents of chloro(2-di-t-butylphosphino-2′,4′,6′-tri-i-propyl-l,r-biphenyl) [2-(2- aminoethyl)phenyl]palladium(II) (t-BuXPhos Palladacycle) was added and degassed with nitrogen for another 10 minutes. The vial was sealed and the reaction was heated at 120 C for 30 minutes in a microwave. LC/MS showed the desired product. The crude was purified with double stacked 50 g amine silica columns eluting with 0- 100%(Ethyl Acetate (10%Methanol)) in hexane over 30 minutes. The pure fractions were combined and concentrated to dryness to afford 15.9 mg of desired product.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,17117-13-4, 2-Bromo-4-ethoxypyridine, and friends who are interested can also refer to it.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; COLLIER, Philip, N.; DAVIES, Robert, J.; DENINNO, Michael, Paul; DOYLE, Elisabeth; FRANTZ, James, Daniel; GOLDMAN, Brian, Anthony; GRILLOT, Anne-Laure; KOLPAK, Adrienne, Lynne; KRAUSS, Raul, Eduardo; LEDFORD, Brian; LIAO, Yusheng; MAGAVI, Sanjay, Shivayogi; MALTAIS, Francois; PEROLA, Emanuele; RYU, Elizabeth, Jin-Sun; SYKEN, Joshua; TANG, Qing; WANG, Tiansheng; (221 pag.)WO2018/106643; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 851484-95-2, 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. 851484-95-2, name is 2-Chloro-5-fluoronicotinaldehyde, molecular formula is C6H3ClFNO, 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.

Example 14; Step 14A: Compound 14a; In a 250 mL flask, 2-chloro-5-fluoropyridine-3-carboxaldehyde (4.88 g, 31.0 mmol) was dissolved in dioxane (103 mL) along with Boc-piperazine (5.77 g, 31. 0 mmol) and potassium carbonate (4.30 g, 31.0 mmol). The reaction was heated to reflux with stirring for 48 hours. The mixture was then diluted with ethyl acetate (100 mL) and washed with saturated NaHC03 solution (2 x 75 mL) and saturated NaCl solution (2 x 75 mL). The organic layer was collected, dried over anhydrous Na2S04, and then filtered. Solvent was removed in vacuo and the residue was purified by column chromatography on silica using 9: 1 hexane/ethyl acetate as the eluent to afford 3. 0g (31%) of the 14a as a yellow solid

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 851484-95-2, 2-Chloro-5-fluoronicotinaldehyde.

Reference:
Patent; NEUROCRINE BIOSCIENCES, INC.; WO2005/42516; (2005); A2;,
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. 55052-27-2, name is 6-Chloro-1H-pyrrolo[2,3-b]pyridine, the common compound, a new synthetic route is introduced below. Recommanded Product: 6-Chloro-1H-pyrrolo[2,3-b]pyridine

a) 6-Chloro-7-aza-3,3-dibromooxindole 6-Chloro-7-azaindole was prepared according to the procedure of Minakata et al; Synthesis, 1992, 661-663.. To a stirred solution of 1.32 g (8.7 mmol) of 6-chloro-7-azaindole in tert-butanol (80 ML) was added 9.9 g (28 mmol) of 90% pyridine hydrobromide perbromide resulting in a thick yellow precipitate forming immediately.. The reaction was concentrated and the crude chromatographed on silica gel eluding with hexane to 90% hexane/10% EtOAc gradient to give 2.36 g of the title compound as a white solid, containing about 30% of 5-bromo-6-chloro-7-aza-3,3-dibromooxindole as an inseparable impurity. 1H NMR (CDCl3) delta 7.16 (d, J=8.0 Hz, 1H), 7.81 (d, J=8.0 Hz, 1H), 9.0 (bs, 1H).. (5-Bromo-6-chloro-7-aza-3,3-dibromooxindole, 8.05 (s, 1H), 9.0 (bs, 1H).

The synthetic route of 55052-27-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Glaxo Wellcome Inc.; US6350747; (2002); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 13445-16-4 , The common heterocyclic compound, 13445-16-4, name is 3-Bromo-2,6-dimethoxypyridine, molecular formula is C7H8BrNO2, 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 2: Preparation of (3aR,4R,6S,6aS)-4-(((tert-butyldimethylsilyl)oxy)methyl)-6-(2,6- dimethoxypyridin-3-yl)-2,2-dimethyltetrahydro-3aH-[l,3]dioxolo[4,5-c] (17d) To a stirred solution of 3-bromo-2,6-dimethoxypyridine (17b) (2.73 g, 12.50 mmol) in Tetrahydrofuran (30 mL) was added n-Butyl lithium (1.6 M solution in hexanes, 7.81 mL, 12.50 mmol) at -78 C and stirred at the same temperature for 1 hr. To the anion formed at – 78 C was added a freshly prepared solution of (3aR,4R,6aS)-4-((tert- butyldimethylsilyloxy)methyl)-2,2-dimethyl-4,6a-dihydro-3aH-[l,3]dioxolo[4,5-c]pyrrole (lk) (2.85 g, 10 mmol) in toluene (1.2 molar solution) over a period of 15 minutes. The reaction stirred for 30 minutes at -78 C, quenched with water (50 mL) and extracted with ethyl acetate (3 x 100 mL). The combined organic layers were washed with water (50 mL), brine (50 mL) dried, filtered and concentrated in vacuum. The crude residue was purified by flash column chromatography (silica gel 40 g, eluting with 0-100% ethyl acetate in hexanes) to afford (3aR,4R,6aS)-4-((tert-butyldimethylsilyloxy)methyl)-6-(2,6-dimethoxypyridin-3- yl)-2,2-dimethyltetrahydro-3aH-[l,3]dioxolo[4,5-c]pyrrole (17d) (1.35 g, 31.8 % yield) as a light brown syrup. 1H NMR (300 MHz, DMSO-d6) delta 7.64 (d, J = 8.1 Hz, 1H), 6.29 (d, J = 8.0 Hz, 1H), 4.42 – 4.28 (m, 2H), 4.09 (d, J = 4.3 Hz, 1H), 3.82 (s, 3H), 3.79 (s, 3H), 3.57 (d, J = 5.0 Hz, 2H), 3.05 (d, J = 4.8 Hz, 1H), 2.85 (s, 1H, D20 exchangeable), 1.40 (s, 3H), 1.17 (s, 3H), 0.82 (s, 9H), -0.00 (d, J= 1.3 Hz, 6H). Mass spec (ES+) 425.1 (M+l).

The synthetic route of 13445-16-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BIOCRYST PHARMACEUTICALS, INC.; BABU, Yarlagadda, S.; KOTIAN, Pravin, L.; BANTIA, Shanta; WU, Minwan; KUMAR, V., Satish; WO2014/78778; (2014); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 83393-46-8, Adding some certain compound to certain chemical reactions, such as: 83393-46-8, name is 1-(1H-Pyrrolo[2,3-b]pyridin-3-yl)ethanone,molecular formula is C9H8N2O, 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 83393-46-8.

A solution of 6.89 g (43.0 mmol) of 1-(1H-pyrrolo[2,3-b]pyridin-3-yl)ethanone in 50 ml of DMF is added dropwise under nitrogen to a suspension of 1.25 g (52.0 mmol) of sodium hydride in 100 ml of DMF. The mixture is stirred at room temperature for one hour and then cooled to 0. A solution of 9.92 g (52.0 mmol) of toluene-4-sulfonyl chloride in 50 ml of DMF is added dropwise, and the reaction mixture is stirred at 0 for 2 hours. The reaction mixture is partitioned between ethyl acetate and water. The organic phase is dried over sodium sulfate, evaporated, and the residue is stirred with water. The residue is filtered off with suction and dried in vacuo: 1-[1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]ethanone as colourless crystals; ESI 315, m.p. 187-189.

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. 83393-46-8, 1-(1H-Pyrrolo[2,3-b]pyridin-3-yl)ethanone, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Dorsch, Dieter; Sirrenberg, Christian; Mueller, Thomas; US2010/173923; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem