Category: pyridine-derivatives

Reference of 90993-26-3, Adding some certain compound to certain chemical reactions, such as: 90993-26-3, name is 7-Bromo-1H-imidazo[4,5-c]pyridine,molecular formula is C6H4BrN3, 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 90993-26-3.

Step 3: 7-bromo-l-((2-(trimethylsilyl)ethoxy)methyl)-lH-imidazo[4,5-c]pyridine 5-oxide To a stirred solution of 7-bromo-lH-imidazo[4,5-c]pyridine 5-oxide (425 mg, 1.99 mmol) and N,N- dimethylformaldehyde (5.5 mL) at 0 C was added N,N-diisopropylethylamine (1.05 mL, 5.96 mmol), tetrabutylammonium iodide (74 mg, 0.199 mmol) and 2-(trimethylsilyl)ethoxymethyl chloride (0.78 mL, 3.97 mmol) and the reaction mixture stirred for 30 min at RT. The reaction mixture was washed with water (10 mL) and extracted with dichloromethane (2 x 10 mL). The combined organic layers were dried over sodium sulfate and concentrated to dryness in vacuo. The resulting residue was purified by column chromatography (silica gel, 100-200 mesh, 0 to 10% methanol in dichloromethane) affording an approximate 3:2 mixture of 7-bromo-l-((2- (trimethylsilyl)ethoxy)methyl)-lH-imidazo[4,5-c]pyridine 5-oxide and 7-bromo-3-((2- (trimethylsilyl)ethoxy)methyl)-3H-imidazo[4,5-c]pyridine 5-oxide N-(2- (trimethylsilyl)ethoxy)methane regioisomers as an orange foam (580 mg, 54%): H NMR (400 MHz, DMSO-d6; reported as an approximate 3:2 mixture of N-(2-(trimethylsilyl)ethoxy)methane isomers) delta 8.73 (d, = 1.5 Hz, 0.6 H), 8.60 (d, = 1.6 Hz, 1H), 8.38 (d, = 1.5 Hz, 1H), 8.36 (d, = 1.5 Hz, 0.6H), 8.10 (s, 1H), 8.09 (s, 0.6H), 5.76 (s, 1.3H), 5.48 (s, 2H), 3.63 – 3.59 (m, 1.4H), 3.56 – 3.50 (m, 2H), 0.97 – 0.91 (m, 3H), -0.01 (s, 9H), -0.02 (s, 6H).

According to the analysis of related databases, 90993-26-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; ESTRADA, Anthony; HUESTIS, Malcolm; KELLAR, Terry; PATEL, Snahel; SHORE, Daniel; SIU, Michael; (260 pag.)WO2016/142310; (2016); 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. 89510-90-7, name is 2-Chloro-5-fluoro-4-pyridinamine, molecular formula is C5H4ClFN2, 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. Formula: C5H4ClFN2

2-(5-chloro-2-methoxy-phenyl)acetic acid (753 mg, 3.75 mmol) in thionyl 1 mL, 68.24 mmol) was stirred at 70 C for 1 hour. The resulting mixture was to dryness and azeotroped with toluene (2 x 10 mL). The crude residue was DMF (10 mL) and treated dropwise with a solution of 2-chloro-5-fluoro-pyridin- 0 mg, 3.41 mmol) in DMF (3 mL) followed by DIPEA (1.49 mL, 8.53 mmol). at room temperature under an inert atmosphere for 16 hours, the mixture was tOAc (100 mL) and washed with water (2 x 50 mL) and brine (2 x50 mL). The on was dried over Na2SO4 and concentrated in vacuo. The crude material was 18 reverse phase chromatography eluting with 0-100% MeCN in water with acid modifier to afford the titled compound as a light yellow solid. 0 MHz, DMSO-d6) delta 10.58 (s, 1H), 8.41 (d, J = 2.7 Hz, 1H), 8.24 (d, J = 5.6 3-7.28 (m, 2H), 7.01 (d, J = 9.5 Hz, 1H), 3.83 (s, 2H), 3.75 (s, 3H). hod E): Rt 1.25 mins; MS m/z 328.9, 330.9= [M+H]+

With the rapid development of chemical substances, we look forward to future research findings about 89510-90-7.

Reference:
Patent; ENTERPRISE THERAPEUTICS LIMITED; COLLINGWOOD, Stephen; MCCARTHY, Clive; HARGRAVE, Jonathan, David; HAY, Duncan, Alexander; SCHOFIELD, Thomas, Beauregard; ELLAM, Sarah; BUXTON, Craig; HABGOOD, Matthew; INGRAM, Peter; MA, Chun Yan; NAPIER, Spencer; SHAIKH, Abdul; SMITH, Matthew; STIMSON, Christopher; WALKER, Edward; (401 pag.)WO2019/145726; (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. 868551-30-8, name is Methyl 4-methyl-5-nitropicolinate. A new synthetic method of this compound is introduced below., Computed Properties of C8H8N2O4

A mixture of methyl 4-methyl-5-nitropyridine-2-carboxylate (39.5g, 0.19mol) and DMF- DMA (30.6 g, 0.26mol, 1.35 eq) in DMF (470 mL) was heated to 90C for 30 min. The solvent was removed in vacuo. The residue (78g) was used without further purification in the next step.

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, 868551-30-8, Methyl 4-methyl-5-nitropicolinate.

Reference:
Patent; PFIZER INC.; WO2005/103003; (2005); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1092286-30-0, 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 1092286-30-0, name is 5-Chloro-2-methyl-3-pyridinecarboxylic acid. This compound has unique chemical properties. The synthetic route is as follows.

Step 1 : 5-Chloro-2-methylnicotinoyl chloride5-Chloro-2-methyl-nicotinic acid (4.15 g, 24.2 mmol) was placed in a flask with DCM (100 ml) and oxalyl chloride (3.68 g, 29 mmol). DMF (200 muIota) was added and the reaction mixture was stirred at RT for 1 hour (gas evolution). The mixture was filtered and the solvent was removed in vacuo to afford the title product which was used in the next step without further purification.

According to the analysis of related databases, 1092286-30-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ATKINSON Benjamin; BEATTIE David; CULSHAW Andrew James; DEVEREUX Nicholas James; MCKENNA Jeffrey; DALE James; WO2011/92293; A1; (2011);,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1235036-15-3 ,Some common heterocyclic compound, 1235036-15-3, molecular formula is C10H11BrClNO2, 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 Example 1.1.10 (100 mg) and tert-butyl 3-bromo-6-chloropicolinate (52.5 mg) in dioxane (2 mL) was added tris(dibenzylideneacetone)dipalladium(0) (8.2 mg), K3P04 (114 mg), 1,3,5,7- tetramethyl-8-phenyl-2,4,6-trioxa-8-phosphaadamantane (5.24 mg) and water (0.8 mL). The mixture was stirred at 95 C for 4 hours, diluted with ethyl acetate and washed with water and brine. The organic layer was dried over Na2S04, filtered, concentrated and purified by flash chromatography, eluting with 20% ethyl acetate in heptanes and then with 5% methanol in dichloromethane, to provide the title compound. MS (ESI) m/e 643.3 (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,1235036-15-3, its application will become more common.

Reference:
Patent; ABBVIE INC.; BENATUIL, Lorenzo; BRUNCKO, Milan; JUDD, Andrew, S.; LI, Yingchun; MCCLUSKEY, Andrew; PHILLIPS, Andrew, C.; PHILLIPS, Darren, C.; SEAGAL, Jane; SOUERS, Andrew, J.; (608 pag.)WO2017/214458; (2017); A2;,
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. 887707-23-5, name is 2-Hydroxy-5-iodo-3-(trifluoromethyl)pyridine. This compound has unique chemical properties. The synthetic route is as follows. HPLC of Formula: C6H3F3INO

A solution of 2-hydroxy-3-(trifluoromethyl)pyridine C in a mixture of N-iodosuccinimide (NIS), acetonitrile, and dimethylformamide (DMF) is heated at 80 C. for 2 hours to produce 2-hydroxy-3-trifluoromethyl-5-(iodo)pyridine I (greater than 80% yield). The 2-hydroxy-3-trifluoromethyl-5-(iodo)pyridine I is then mixed with POCl3 in DMF and heated to 130 C. in a microwave for 20 minutes to produce 2-chloro-3-trifluoromethyl-5-(iodo)pyridine J (yield of 50 to 55%). The 2-chloro-3-trifluoromethyl-5-(iodo)pyridine K is reacted in a solution of pMBnNH2, palladium(II) acetate, 2,2?-bis(diphenylphosphino)-1,1?-binaphthyl (BINAP), triethylamine, and cesium carbonate in toluene to produce 5-((4-methoxyphenyl))methylamino)-2-chloro-3-(trifluoromethyl)pyridine K (yield of 40%). The 5-((4-methoxyphenyl))methylamino)-2-chloro-3-(trifluoromethyl)pyridine K is reacted in a solution of zinc cyanide, tris(dibenzylideneacetone)dipalladium (Pd2(dba)3), and 1,1?-bis(diphenylphosphino)ferrocene (dppf) in DMF to provide 5-(4-methoxybenzylamine)-2-cyano-3-(trifluoromethyl)pyridine K (yield of 92%). The 5-(4-methoxybenzylamine)-2-cyano-3-(trifluoromethyl)pyridine K is reacted in a solution of dichloromethane and trifluoroacetic acid to provide 2-cyano-3-trifluoromethyl-5-(amino)pyridine H (yield greater than 95%). The 2-cyano-3-trifluoromethyl-5-(amino)pyridine H is reacted with thiophosgene in water at 25 C. for 2 hours to provide 5-isothiocyanato-3-(trifluoromethyl)pyridine-2-carbonitrile A (yield of 74% to 95%).

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, 887707-23-5, 2-Hydroxy-5-iodo-3-(trifluoromethyl)pyridine.

Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; Jung, Michael E.; Sawyers, Charles L.; Ouk, Samedy; Tran, Chris; Wongvipat, John; (28 pag.)US9388159; (2016); B2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 211308-81-5, 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 211308-81-5 as follows.

Preparation 5 : 5-Chloro-l/T-pyrrolo[2,3-b]pyridine-2-carboxylic acid; Pyruvic acid (0.43ml, 6.24mmol) was added to a solution of 5-chloro-3-iodopyridin-2-ylamine (Preparation 4, 500mg, 2.08mmol), palladium acetate (23mg, O.lOmmol) and DABCO (700mg, 6.24mmol) in anhydrous DMF (2OmL). The reaction mixture was degassed with argon for 20min, then heated to HO0C for 16h. The solvent was removed in vacuo and the residue suspended in water (1OmL) and acetic acid (5mL) and then filtered. The solid was dissolved in EtOAc (5OmL), extracted into 2N NaOH solution (5OmL) and the organic layer discarded. The aqueous solution was acidified with concentrated HCl and extracted into EtOAc (2x40mL). The combined organics were dried (MgSO4) and concentrated in vacuo to give the title compound as a beige solid. deltaH (CD3OD): 7.14 (IH, s), 8.14 (IH, d), 8.35 (IH, d).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,211308-81-5, its application will become more common.

Reference:
Patent; PROSIDION LIMITED; WO2006/59164; (2006); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 228410-90-0 ,Some common heterocyclic compound, 228410-90-0, molecular formula is C6H5BrN2O3, 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 5-bromo-4-methyl-3-nitropyridin-2-ol (24 g, 103 rnmol) in DMF (200 ml) was added K2CO3 (21.39 g, 155 mmol) and CH3I (21.86 g, 155 mmol). The reaction mixture was stirred at room temperature for 2h. The reaction mixture was poured into ice cold water, the solid formed was filtered and dried under vacuum to afford title compound as off white solid (23.5 g, 92 %). FontWeight=”Bold” FontSize=”10″ H NMR (400 MHz, DMSO-d6) delta 8.40 (s, 1H), 3.51 (s, 3H), 2.21 (s, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,228410-90-0, its application will become more common.

Reference:
Patent; AURIGENE DISCOVERY TECHNOLOGIES LIMITED; BORUAH, Anima; CHITTY VENKATA, Srikanth; HOSAHALLI, Subramanya; PANIGRAHI, Sunil Kumar; WO2014/125408; (2014); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 94220-38-9, 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.94220-38-9, name is 7-Chloro-5-methyl-1H-pyrazolo[4,3-b]-pyridine, molecular formula is C7H6ClN3, molecular weight is 167.5956, as common compound, the synthetic route is as follows.

EXAMPLE 6 7-[3-Dimethylaminopropylamino]-5-methyl-1H-pyrazolo[4,3-b]pyridine (E6) STR20 The title compound was prepared from 7-chloro-5-methyl-1H-pyrazolo[4,3-b]pyridine (D4) and 3-dimethylaminopropylamine by the method given in Example 2. On neutralization of the thus formed hydrochloride salt a clear solution was produced. After freeze drying, purification was carried out on Dowex 50W as described in Example 4, followed by crystallization from ethyl acetate to give the title compound as a white crystalline solid, m.p. 112-117. delta(DMSO-d6) 1.55-2.0 (2H,m), 2.23 (3H,s), 2.30-2.55 (2H,m), 3.1-3.5 (2H,m), 6.25 (1H,s), 6.72 (1H,br.t, J=4 Hz), 7.94 (1H,s).

The chemical industry reduces the impact on the environment during synthesis 94220-38-9, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Beecham Group p.l.c.; US4670432; (1987); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 23628-31-1, 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. 23628-31-1, name is 6-Aminopicolinic acid, molecular formula is C6H6N2O2, 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.

Step 1. Preparation of ethyl 6-aminopicolinate (78):To a solution of 2-amino-6-pyridinecarboxylic acid 77 (6.0 g, 43.5 mmol) in ethanol (150 mL) was added thionyl chloride (12.0 g, 101 mmol) at 0 0C. The resulting reaction mixture was stirred at reflux for 12 h. Upon cooling to room temperature, the reaction mixture was concentrated under reduced pressure. Saturated aqueous Na2CO3 solution was added until the pH of the solution reached 9. The mixture was concentrated under reduced pressure and dichloromethane (150 mL) was added to the resulting residue. The mixture was stirred vigorously at room temperature for 30 min and then filtered. The filtrate was concentrated under reduced pressure to afford 78 (5.5 g, 76 % yield).

According to the analysis of related databases, 23628-31-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SIRTRIS PHARMACEUTICALS, INC.; OALMANN, Christopher; PERNI, Robert, B.; VU, Chi, B.; WO2010/37127; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem