Category: pyridine-derivatives

Electric Literature of 89694-10-0, 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 89694-10-0, name is 2-Methoxy-3-methyl-5-nitropyridine. This compound has unique chemical properties. The synthetic route is as follows.

A yellow solution of 2-methoxy-3-methyl-5-nitropyridine (68.8 g, 409 mmol) and tert-butyl 2-chloroacetate (77.0 g, 511 mmol) in THF (1 L) was stirred and cooled to -20 C. in a dry ice/isopropanol bath. Potassium tert-butoxide (115 g, 1.02 mol) was added at a rate so that the reaction temperature was less than -10 C. The reaction mixture turned dark purple. When the addition was complete, the cooling bath was removed and the reaction was stirred for 30 min. The stirred reaction mixture was quenched with HCl (500 mL, 2.4 N). The purple solution turned pale yellow and the mixture separated into two layers. The organic layer was separated, washed three times with brine, and concentrated in vacuo. Hexane was added to the amber residue. The mixture was concentrated in vacuo and then dried under high vacuum for 1 hr to give tert-butyl 2-(6-methoxy-5-methyl-3-nitropyridin-2-yl)acetate (83.4 g, 72% yield) as a tan solid: 1H NMR (400 MHz, CDCl3) delta 8.16 (s, 1H), 4.09 (s, 2H), 4.02 (s, 2H), 2.21 (s, 3H), 1.44 (s, 9H); 13C NMR (100 MHz, CDCl3) delta 168.81, 163.63, 147.88, 139.41, 135.19, 120.82, 81.66, 54.69, 44.48, 28.03, 15.27. An analytical sample was recrystallized from hexane to give white needles, mp 71-72.5 C. Anal. calcd. for C13H18N2O5: C, 55.31, H, 6.42, N, 9.92. Found: C, 55.52, H, 6.40, N, 9.84.

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 89694-10-0, 2-Methoxy-3-methyl-5-nitropyridine.

Reference:
Patent; Bristol-Myers Squibb Company; US2010/29684; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 90145-48-5, Adding some certain compound to certain chemical reactions, such as: 90145-48-5, name is 5-Bromopyridine-2-carboxamide,molecular formula is C6H5BrN2O, 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 90145-48-5.

Phosphorus oxychloride (111 g, 0.720 mol) was added to a mixture of 5-bromopicolinamide (D8) (58 g, 0.288 mol) in dry toluene (300 ml) The mixture was heated to reflux for 2 hours. The mixture was poured into ice/water, and basified to pH=12 with 2N NaOH. The resulting mixture was extracted with ethyl acetate and the organic phase was washed with brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by column chromatography on silica gel eluting with a mixture petroleum ether/ethyl acetate 10:1. Collected fractions, after solvent evaporation afforded the title compound (D9) (43.6 g) as a yellow solid.

According to the analysis of related databases, 90145-48-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Borriello, Manuela; Rovati, Lucio; Stasi, Luigi Piero; Buzzi, Benedetta; Colace, Fabrizio; US2013/261100; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 727356-19-6, name is 2-Bromo-6-(chloromethyl)pyridine. This compound has unique chemical properties. The synthetic route is as follows. Product Details of 727356-19-6

Part II: Preparation of (6-bromo-pyridin-2-ylmethyl)-(4-fluorophenyl)-carbamic acid terf-butyl esterTo a solution of (4-fluorophenyl)-carbamic acid terf-butyl ester (60144-53-8, 750 mg, 3.55 mmol) in tetrahydrofuran (10 ml.) was added sodium hydride (60% dispersion in mineral oil, 150 mg, 3.9 mmol). After 30 minutes, tetra-n-butylammonium iodide (51 mg, 0.36 mmol) and 2-bromo-6-chloromethyl-pyridine (804 mg, 3.9 mmol) was added to the reaction and the mixture was heated to 70C. After 1 hour, the reaction was cooled to room temperature, quenched with saturated sodium bicarbonate (10 ml.) and extracted with ethyl acetate (2 x 15 ml_). The organic phases were combined, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. Flash chromatography (silica gel; 10% ethyl acetate in hexanes) provided (6-bromo-pyridin-2-ylmethyl)-(4-fluorophenyl)-carbamic acid terf-butyl ester (700 mg, 1.84 mmol) as an oil which solidified upon standing.

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, 727356-19-6, 2-Bromo-6-(chloromethyl)pyridine.

Reference:
Patent; WYETH; WO2008/73936; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 886365-47-5 , The common heterocyclic compound, 886365-47-5, name is 1-(5-Bromo-2-chloropyridin-3-yl)ethanone, molecular formula is C7H5BrClNO, 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.

Preparation of 5-bromo-3-methyl-1H-pyrazolo[3,4-b]pyridine (D-2-6).A mixture of compound D-2-5 (4 g, 16 mmol) and hydrazine (30 mL) in ethanol (300 mL) was stirred at room temperature overnight. TLC (petroleum ether/EtOAc 5:1 ) indicated complete consumption of starting material. The reaction mixture was concentrated in vacuo and the residue was purified via column chromatography (silica gel, petroleum ether/EtOAc 15:1 ) to yield crude compound D-2-6, which was further purified by preparative HPLC to yield pure compound D-2-6 (800 mg, yield: 20%) as a white solid.

The synthetic route of 886365-47-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER INC.; WO2009/16460; (2009); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 2897-43-0 ,Some common heterocyclic compound, 2897-43-0, molecular formula is C5H3Cl2N3O2, 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.

To a solution of 2,6-dichloro-3-nitro-pyridin-4-amine (2.6 g, 14.4 mmol) from Step A in MeOH (150 mL) was added Raney Nickel catalyst (2 g) and the reaction agitated under a hydrogen atmosphere in a Parr apparatus (35 p.s.i.) for 2 h . The reaction mixture was filtered through a pad of Celite and concentrated to yield the title compound. MS: m/z = 179 (M + 1).

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. 2897-43-0, 2,6-Dichloro-3-nitropyridin-4-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK & CO., INC.; WO2007/61694; (2007); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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 86847-84-9, name is N-(6-Chloropyridin-2-yl)pivalamide. This compound has unique chemical properties. The synthetic route is as follows. category: pyridine-derivatives

B. 1 N-(6-chloro-3-iodopyridin-2-yl)pivalamide[0336] To a solution of N-(6-chloropyridin-2-yl)pivalamide (15.8 g, 74.2 mmol) in anhydrousTHF (150 mL) at -78 0C under a nitrogen atmosphere, is added 1.7 M -butyllithium in pentane (96 mL, 163 mmol, 2.2 eq.) dropwise (dropping funnel) over 0.5 h. The reaction mixture is then stirred at -78 0C for 3 h before iodine (22.6 g, 89 mmol, 1.2 eq.) in THF (60 mL) is slowly added in one portion. After 10 min., the cooling bath is removed and the reaction is allowed to warm to rt and stirred for 2 h. Hydrochloric acid (1 M, 75 mL) is then added to the reaction reaction mixture. The reaction mixture is concentrated in vacuo (rotary evaporator) to remove the THF, the resulting mixture is extracted with ethyl acetate (800 mL). The phases are separated and the organic layer is washed with aqueous 1 M Na2S2theta3 (100 mL), brine (300 mL x2), water (300 mL), dried over MgSO/t, and evaporated. The crude product is recrystalized from DCM/hexanes (1 :4) and the solid that forms collected by filtration to provide N-(6-chloro-3-iodopyridin-2-yl)pivalamide as a white crystalline solid (17.2 g). The filtrate is evaporated and the residue chromatographed on a silica gel column (hexanes/EtOAc, 9/1) to provide an additional product (2.5 g). Overall 19.7 g (78% yield) of N-(6-chloro-3-iodopyridin-2-yl)pivalamide is obtained. 1H NMR (300 MHz, DMSO-^6), delta 9.86 (s, IH), 8.30 (d, J = 8.4 Hz, IH), 7.20 (d, J = 8.4 Hz, IH), 1.23 (s, 9H). LCMS-ESI (m/z): calcd for C10H12ClIN2O 337.9; [M+H]+ found 339.0.

With the rapid development of chemical substances, we look forward to future research findings about 86847-84-9.

Reference:
Patent; GALAPAGOS N.V.; BURRITT, Andrew; WO2008/65198; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 89167-34-0, 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 89167-34-0 as follows.

A mixture of 4-chloro-3-iodopyridine (1.50 g, 6.30 mmol, prepared according to Tabanella, S. et al. Org. Biomol. Chem. 2003, 1, 4254-4261.), 2-fluoro-nitrophenol (Lancaster, 2.0 g, 12.7 mmol), DIPEA (5 mL), and NMP (10 mL) was heated at 150 C. After 12 h, more 2-fluoro-nitrophenol (0.50 g, 3.18 mmol) was added to the reaction mixture and heating was continued for 4 h. Most of the volatile components were removed under vacuum at 75 C., the residue treated with saturated aq. NaHCO3 solution (150 mL) and extracted with EtOAc (2×100 mL). The combined extracts were washed with brine, dried (MgSO4) and concentrated in vacuo to give the crude product. Purification by flash chromatography on silica gel, using 0-100% CH2Cl2/hexanes then 2% MeOH/CH2Cl2 gave the title compound (1.0 g, 43%) as a yellow solid. 1H NMR (DMSO-d6) delta 8.96 (s, 1H), 8.47 (d, 2H, J=5.5 Hz), 8.44 (dd, 1H, J=2.7, 9.2 Hz), 7.49 (dd, 1H, J=8.8, 8.2 Hz), 7.07 (d, 1H, J=5.5 Hz); MS (ESI+): m/z 361.05 (M+H)+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,89167-34-0, its application will become more common.

Reference:
Patent; Borzilleri, Robert M.; Cornelius, Lyndon A.M.; Schmidt, Robert J.; Schroeder, Gretchen M.; Kim, Kyoung S.; US2005/245530; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 867034-10-4 ,Some common heterocyclic compound, 867034-10-4, molecular formula is C10H9ClN2O2, 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.

To a heterogeneous solution of potassium ethoxide (6.56 g, 77.9 mmol) in diethyl ether (55 mL), was slowly added diethyl oxalate (10.6 mL, 77.9 mmol). A slight exotherm resulted. After stirring 5 min, a homogeneous yellow solution resulted, but after 10 min, a heterogeneous yellow slurry was observed. Addition of 2-chloro-4-methyl-3-nitropyridine (13.45 g, 77.9 mmol) as a solid, with a diethyl ether rinse (23 mL), resulted in a dark violet solution with a dark precipitate. The mixture was stirred at room temperature overnight (21 h). The solid precipitate was filtered, rinsed thoroughly with diethyl ether, and air-dried to give potassium (lZ)-1-(2-chloro-3- nitropyri din-4-yl)-3-ethoxy-3-oxoprop-1-en-2-olate (19.8 g, 63.6 mmol, yield 81%) as an orange solid. The crude product was used directly without further purification or identification.Potassium (lZ)-l-(2-chloro-3-nitropyridin-4-yl)-3-ethoxy- 3-oxoprop-1-en-2-olate (19.8 g, 63.6 mmol) was dissolved in acetic acid (908 mL) and the solution was treated with iron powder (14.6 g, 280.9 mmol). The reaction mixture was warmed to 60C and stirred overnight (18.5 h). TLC analysis indicated consumption of the starting material, therefore the reaction mixture was filtered through diatomaceous earth to remove the catalyst. The filtrate was concentrated to dryness. The residue was treated with methylene chloride (ca. 400 mL) and filtered through a plug of silica. Eluting with methylene chloride removed insolubles, and further elution with methylene chloride/ethyl acetate (50: 50) provided ethyl 7- chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylate (10.3 g, 45.8 mmol, yield 72%) as a yellow solid after concentration: Rf 0.80 (silica gel, 50:50 hexanes/ethyl acetate) ; mp 152-157C; (at)H NMR (300 MHz, CD30D) 81.43 (3H, t, J = 7.0 Hz), 4.44 (2H, q, J = 7.1 Hz), 7.27 (lH, s), 7.65 (1H, d, J = 5.7 Hz), 7.95 (1H, d, J = 5.4 Hz); ESI MS m/z 224 [C10H9ClN2O2 + H] +; HPLC (Method A) >99% (AUC) , tR = 16. 6 min.Ethyl 7-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylate (0.64 g, 2.85 mmol) was dissolved in tetrahydrofuran (5.7 mL) and methanol (6.8 mL). To the mixture was added 3 N KOH (2.85 mL). After stirring overnight (15.5 h) at room temperature, the reaction mixture was concentrated to dryness. The residue was dissolved in water. This aqueous solution was made acidic (pH 3 using 6 N HCl. The precipitate was collected by filtration. The precipitate was dissolved in methanol and concentrated to dryness to afford 7-chloro-lH-pyrrolo[2,3- c] pyridine-2-carboxylic acid (0.53 g, 2.7 mmol, 94%) as a yellow powder: mp 210-214C; ¹H NMR (300 MHz, CD30D) 87.25 (lH, s), 7.65 (lH, d, J = 5.4 Hz), 7.94 (lH, d, J = 5.4 Hz) ; ESI MS m/z 195 [C8H5ClN2O2 – H]-; HPLC (Method A) >99% (AUC) , tR = 12.2 min.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,867034-10-4, its application will become more common.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; WO2005/97129; (2005); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 4434-13-3, 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 4434-13-3 as follows.

To a mixture of 5-methylpicolinic acid (13.7 g) and thionyl chloride (150 mL) was added sodium bromide (20.6 g) by small portions, and the mixture was heated under reflux under a nitrogen atmosphere for 1 hr. DMF (2 mL) was added and the mixture was further heated under reflux under a nitrogen atmosphere for 16 hr. An operation to add toluene (100 mL) to the reaction mixture and evaporate the solvent under reduced pressure was repeated twice, and toluene (100 mL) was added to the obtained residue. To a mixture thereof were added DIPEA (25.8 g) and methanol (20 mL) under a nitrogen atmosphere at 0C, and the mixture was further stirred at 20C for 2 hr. The solvent was evaporated under reduced pressure and the obtained residue was purified by silica gel column chromatography (ethyl acetate/petroleum ether) to give the title compound (9.40 g). 1H NMR (400 MHz, CDCl3) delta2.43 (3H, s), 3.99 (3H, s), 8.10 (1H, s), 8.54 (1H, s).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,4434-13-3, its application will become more common.

Reference:
Patent; Takeda Pharmaceutical Company Limited; OGINO, Masaki; KIMURA, Eiji; SUZUKI, Shinkichi; ASHIZAWA, Tomoko; IMAEDA, Toshihiro; FUJIMORI, Ikuo; ARAI, Ryosuke; (82 pag.)EP3156397; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 66909-38-4, Adding some certain compound to certain chemical reactions, such as: 66909-38-4, name is 6-Chloro-4-methylpyridin-3-amine,molecular formula is C6H7ClN2, 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 66909-38-4.

2-Chloro-4-methyl-5-nitropyridine (lg, 5.8 mmol) was dissolved in EtOH (60 mL). AcOH (4 mL) and Fe (5 eq. ) were added and the mixture was refluxed at 80C overnight. The mixture was filtered through celite and reduced under vacuum to afford the crude 5-amino-2-chloro-4-methylpyridine which was used in the next step with no further purification. The amine was dissolved in cone. HC1 (6 mL), transferred to a 3-neck round bottom flask, and cooled to-5 C. A solution of NaNO2/H2O (440 mgs/5 mL) was slowly added and the mixture was allowed to stir for 10 mins. To a second, separate 3-neck round bottom flask was added H20 (12 mL) and cooled to-5 C. Thionyl chloride (4.5 eq. ) was then added dropwise. After complete addition the mixture was allowed to warm to room temp. Whereupon CuCl (. 05 eq. ) was added and the mixture was then cooled back down to -5C. The first reaction mixture, containing the amine precursor, was slowly added to the second reaction mixture. A froth formed and was filtered off to afford 6-chloro-4-methyl-pyridine-3-sulfonyl chloride which was used in the next step with no further purification. The title compound was synthesized from 2- [2- (R, S)-3-oxo-1, 2,3, 4-tetrahydro-quinoxalin-2-yl]-N- (pyrid- 4-yl) ethyl acetamide and 6-chloro-4-methyl-pyridine-3-sulfonyl chloride using Method G. MS ni/z (M+H) 501.4 ; HPLC (CH3CN-H2O-0.1% TFA): Rt= 2.05 min.

According to the analysis of related databases, 66909-38-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ELAN PHARMACEUTICALS, INC.; WO2003/93245; (2003); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem