Day: April 11, 2022

Synthetic Route of 16744-81-3, Adding some certain compound to certain chemical reactions, such as: 16744-81-3, name is 4-Methoxypicolinaldehyde,molecular formula is C7H7NO2, 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 16744-81-3.

Examples; Final products; 1. (R. S)-2- [3-F4-METHOXYPYRIDIN-2-Y)) PROP-2-Y .]-3H-IMIDAZO [4. 5-B] PYRIDINE HYDROCHTORIDE; A solution of 0.59 g of 4METHOXYPYRIDINE-2-CARBALDEHYDE (Ashimori et al., Chem. Pharm. Bull. 38,2446- 2458 (1990) ) in 19 ml of methanol is treated with 1.9 g of {1- (3H-imidazo [4,5-b] pyridin-2-yl)-ethyl}- triphenyl-phosphonium chloride (compound A1). 3.3 ml of a solution of sodium methanolate in methanol (1.3 M) are added dropwise at 50° C. The reaction mixture is stirred at 50°C for 4 h and evaporated to dryness. The resulting residue is chomatographed on silica gel using DICHLOROMETHANE/METHANOL 20: 1 to give 1.75 g of a colorless, amorpheous solid, which is dissolved in 190 ml of methanol. 1.5 ml of glacial acetic acid and 388 mg of palladium on active carbon (10percent Pd) are added and the suspension is stirred at room temperature for 2.5 d under hydrogen atmosphere. Then the catalyst is filtered off and the reaction mixture is concentrated to dryness. After CHROMATOGRAPHICAL purification of the residue on silica gel (DICHOROMETHANE/METHANOL 25: 1) and evaporation of the eluents, 837 mg of an oil are obtained, which is dissolved in 160 ml of DICHLOROMETHANE. 2 ml of an ethereal hydrochloric acid solution (2.0 M) are added to the solution under ice-cooling. After LYOPHILLIZATION from dioxane, 0.951 g of the title compound are obtained as a colorless LYOPHILISATE. M. p. 61 °-64°C. MS: 269.1 (MH+). TLC: Rf = 0.44 (dichloromethane/methanol 10: 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. 16744-81-3, 4-Methoxypicolinaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ALTANA PHARMA AG; WO2005/30768; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 109880-43-5, 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.109880-43-5, name is Methyl 4-chloro-6-(hydroxymethyl)picolinate, molecular formula is C8H8ClNO3, molecular weight is 201.61, as common compound, the synthetic route is as follows.

1.5 g of compound 13 (7.4 mmol, 1 eq.) are dissolved in 200 mE dichloromethane and 3 mE triethylaminc are added (22.2 mmol, 3 eq.). Then 0.87 mE of mesyl chloride is added (11.1 mmol, 1.5 eq.) slowly and a progressive yellow coloring of the mixture is observed. The reaction progress is followed by CCM and stopped after 30 mm. 100 mE of a saturated solution of NaHCO4 are added and the organic phase is washed with water (up to pH=7) and brine. The organic solution is then dried on Na2SO4 and evaporated to give 2 g of a yellow oil of compound 14 used without thrther purification (quantitative yield). ?H-NMR (300 MHz, CDC13) oe (ppm)=8.1 (s, 1H),7.68 (s, 1H), 5.40 (s, 2H), 4.01 (s, 3H), 3.17 (s, 3H).

The chemical industry reduces the impact on the environment during synthesis 109880-43-5, I believe this compound will play a more active role in future production and life.

Reference:
Patent; ECOLE NORMALE SUPERIEURE DE LYON; CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE; UNIVERSITE CLAUDE BERNARD LYON I; COMMISSARIAT A L’ENERGIE ATOMIQUE ET AUX ENERGIES ALTERNATIVES; MAURY, Oliver; GIRARD, Eric; ENGILBERGE, Sylvain; RIOBE, Francois; (76 pag.)US2018/362550; (2018); 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.4966-90-9, name is 4-Hydroxy-6-methyl-3-nitropyridin-2(1H)-one, molecular formula is C6H6N2O4, molecular weight is 170.12, as common compound, the synthetic route is as follows.category: pyridine-derivatives

Part A A mixture of 6-methyl-3-nitropyridine-2,4-diol (50 g, 0.29 mol) and phosphorus oxychloride (500 mL) was heated at 90 C. overnight. The excess phosphorus oxychloride was removed under reduced pressure. The resulting black oil was poured into water (1.8 L) and ice. This mixture was extracted with chloroform (*8, 3L total) and filtered to remove black particulates and break up an emulsion. The combined organics were washed with 10% sodium carbonate (*2) and brine, dried and then concentrated under reduced pressure to provide 52 g of an amber oil. This oil was recrystallized from heptane (115 mL) to provide 43.5 g of 2,4-dichloro-6-methyl-3-nitropyridine as large amber crystals.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,4966-90-9, 4-Hydroxy-6-methyl-3-nitropyridin-2(1H)-one, and friends who are interested can also refer to it.

Reference:
Patent; 3M Innovative Properties Company; US6545016; (2003); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 2789-25-5, 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 2789-25-5, name is 2-Chloro-3-nitropyridin-4-amine. This compound has unique chemical properties. The synthetic route is as follows.

3c) 4-amino-2-hydroxy-3-nitropyridine A solution of 18.0 g (104 mmol) of 4-amino-2-chloro-3-nitropyridine in 120 ml dimethylsulphoxide and 30 ml of water was stirred for four hours at 130 C. The solution was then cooled and left to stand overnight while cooling with ice. The product that crystallized out was suction filtered, washed with a little water and dried at 50 C. Yield: 69% of theory. C5H5N3O3 (155.11) Mass spectrum: (M+H)+=156 (M-H)-=154

According to the analysis of related databases, 2789-25-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Boehringer Ingelheim Pharma GmbH Co. KG; US2005/20574; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 98121-41-6, 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. 98121-41-6, name is 3-Amino-5,6-dichloropyridine, molecular formula is C5H4Cl2N2, 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.

To a solution of 5,6-dichloro-pyridin-3-ylamine (40.0 g, 0.245 mol, 1.0 equiv.) in dichloromethane (300 mL) at 0 C was added boron trifluoride diethyl etherate (42.0 g, 0.296 mol, 1.2 equiv.) followed by 2-methyl-2-nitrosooxy-propane (38.0 g, 0.369 mol, 1.5 equiv.). The resulting reaction was allowed to warm to 25 C. The slurry of the product was stirred at this temperature for 30-60 min and filtered to afford 5,6-dichloro-pyridine-3-diazonium tetrafluoroborate (51.0 g, 0.195 mol).5,6-Dichloro-pyridine-3-diazonium tetrafluoroborate (180 g, 0.688 mol, 1.0 equiv.) was dissolved in Ac2O (540 mL) and stirred at RT for a few minutes. Then, the mixture was heated to 60 C. Acetic acid 5,6-dichloro-pyridin-3-yl ester was detected by LCMS. The acetic acid was evaporated, the precipitate was diluted with DCM and evaporated in vacuo. The mixture was purified on silica gel (1% EtOAc in petroleum ether as eluent) to afford acetic acid 5,6-dichloro-pyridin-3-yl ester (84.0 g, 0.408 mol).

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 98121-41-6, 3-Amino-5,6-dichloropyridine.

Reference:
Article; Duplessis, Martin; Morency, Louis; James, Clint; Minville, Joannie; Deroy, Patrick; Morin, Sebastien; Thavonekham, Bounkham; Tremblay, Martin; Halmos, Ted; Simoneau, Bruno; Bousquet, Yves; Sturino, Claudio; Tetrahedron Letters; vol. 54; 19; (2013); p. 2303 – 2307;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 17570-98-8, 2-(Bromoacetyl)pyridine hydrobromide, 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, HPLC of Formula: C7H7Br2NO, blongs to pyridine-derivatives compound. HPLC of Formula: C7H7Br2NO

General Procedure 2: Formation of an imidazole by sequential treatment of an amidine with LiHMDS and a heteroaryl-halomethylketone in THF followed by dehydration of the intermediate hvdroxyimidazoli?e in hot acetic acid.; A 1.0 M solution of LiHMDS in THF (Aldrich Chemical Co., 1.0-1.2 equiv, or 2.2 equiv when the heteroaryi-halomethyfketone is a hydrobromide salt) is added dropwise to a solution of the amidine (1.0 equiv) in anhydrous THF (generally 2-4 mL/mmol amidine) at -20 0C to 50C under nitrogen and the resulting solution stirred at about 0 0C for 10-30 min. A solution of the haloketo?e (1.0-1.5 equiv, in equal or greater amount relative to the lithium base) in anhydrous THF (1-3 mL per mmol) is added in one portion. The resulting mixture is stirred in an ice bath for 10-30 min and then at RT for at least 30 min. Water and organic solvent (usually EtOAc or DCM) are added and the product is isolated by extraction into the organic layer which is dried and concentrated. The resulting crude product, which generally contains hydroxy-imidazoline, the target imidazole, and unreacted amidine (HPLCMS analysis) is dissolved in acetic acid (5-25 mUmmol) and heated at 60-1000C for 20-60 min (HPLCMS showing disappearance of the hydroxy-imidazoline peak). This mixture is concentrated, and the crude product isolated by extraction using aqueous NaOH and organic solvent (usually EtOAc or DCM), and residual amidine removed by washing with aqueous citric acid. If not otherwise specified, the product was purified by SGC (gradient of MeOH in DCM, 0.5% NH4OH). In the following Example section, compounds of formula I are designated as Example 1, Example 2, and so on, whereas the corresponding synthetic intermediates are designated Preparation 1 A , Preparation 1 B, or Preparation 2A; Example 4; i-(4-(4-fpvridin-2-vO-1 -fpyrimidin-5-vl)-1 H-imidazol-2-vltohenvl)-1 H-pvrrolof2.3-biDvridine; According to General Procedure 2, NI-(pyrimidi?-5-yl)-4-(1H-pyrrolo[2l3-b]pyridin-1- yl)benzamidine (447 mg, 1.42 mmol) and 2-bromo-1-(pyridin-2-yl)ethanone hydrobromide (400 mg, 1.42 mmol) gave the title substance as a yellow solid. Yield 80 mg, 13.5% of theory. 1H NMR (CDCI3) delta 9.24 (s, 1H), 8.77 (s, 2H)1 8.58 (m, 1H), 8.35 (del, 1H1 J = 1.7, 4.6), 8.13 (d, 1H, J = 7.9), 7.95 (dd, 1H, J =1.5, 7.7), 7.90 (s, 1H), 7.87 (m, 2H), 7.77 (m, 1H), 7.57 (m, 2H), 7.52 (d, 1H, J = 3.7), 7.20 (m, 1H), 7.13 (dd, 1H1 J = 5.0, 7.9), 6.64 (d, 1H, J = 3.7). MS (AP+) m/beta 416 (MH+). IC50 = 13.6 nM

At the same time, in my other blogs, there are other synthetic methods of this type of compound,17570-98-8, 2-(Bromoacetyl)pyridine hydrobromide, and friends who are interested can also refer to it.

Reference:
Patent; PFIZER PRODUCTS INC.; WO2008/4117; (2008); 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.298709-29-2, name is 3,5-Difluoropicolinonitrile, molecular formula is C6H2F2N2, molecular weight is 140.0903, as common compound, the synthetic route is as follows.SDS of cas: 298709-29-2

Intermediate 45 l-(3,5-Difluoropyridin-2-yr)ethanoneA solution of methylmagnesium bromide (36.8 ml, 117.78 mmol) in THF (50ml) was stirred under N2 and cooled to -78C. 3,5-difluoropicolinonitrile (15.0 g, 107.07 mmol) in THF (50 ml) was added drop wise with an addition funnel at such a rate that the internal temp, was kept below -4C. After the addition was complete, the reaction was poured into a IM HCl (100 ml, chilled in an ice bath). The reaction was stirred at 00C for 30 minutes and r.t. for 30 minutes. To this solution 150 ml of EtOAc was added to extract product. The aqueous phase was neutralized to pH9 with NaHCO3 and extracted with EtOAc (2 X 20 ml). The organic phase were combined and the volatiles were removed under reduced pressure. Purification by ISCO (0-10% EtOAc- hexanes) gave the title compound as light yellow oil. LC-MS: 158 [M+H].

At the same time, in my other blogs, there are other synthetic methods of this type of compound,298709-29-2, 3,5-Difluoropicolinonitrile, and friends who are interested can also refer to it.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2008/132502; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 132521-70-1, 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 132521-70-1 as follows.

A mixture of 6-(4-methylpiperazin- 1 -yl)nicotinicacid (50 mg, 0.226 mmol), tert-butyl 2-amino-4-(thran-3- yl)phenylcarbamate (62 mg, 0.226 mmol) and EDCI (95 mg, 0.5 mmol) in pyridine (5 mE) was stirred at room temperature for overnight. The mixture was poured into water (20 mE) and extracted with EA to afford crude (170 mg, crude).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,132521-70-1, its application will become more common.

Reference:
Patent; Regenacy Pharmaceuticals, LLC; van Duzer, John H.; Mazitschek, Ralph; (123 pag.)US2018/141923; (2018); 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. 1186608-73-0, name is 3-Methyl-1H-pyrazolo[3,4-b]pyridin-5-amine. A new synthetic method of this compound is introduced below., HPLC of Formula: C7H8N4

EXAMPLE 4: 5-Bromo-3-methyl-lH-pyrazolo-r3,4-&1pyridineA stirred solution 3-Methyl-lH-pyrazole[3,4-b]pyridin-5-amine (200mg, 1.35mmol) in 48% hydrobromic acid (1.46ml, 27.02mmol) and water (1.5ml) was cooled to -5 C. A solution of sodium nitrite (lOOmg, 1.47mmol) in water (0.5ml) was added to this reaction mixture at 0 C. Then this reaction mixture was added to a suspension of copper (I) bromide (300mg, 2.02mmol) in 48% hydrobromic acid (0.4ml) maintained at 0C. Reaction mixture was stirred for 4h at RT. Reaction mixture was extracted with ethyl acetate. The extract was washed with water (3x 20ml) and sodium carbonate solution (2x 15ml). The combined organic layer was dried over anhydrous sodium sulphate, filtered and concentrated. Purification was done by flash column over 230-400 mesh silica gel eluting with 25% ethyl acetate/ petroleum ether to get the desired product 6, lOOmg (Yield -35%) as white solid. The product was confirmed by 1HNMR and MS spectrum analysis. 1H NMR (400 MHz, CDC13) delta: 10.92 (bs, 1H), 8.59 (s, 1H), 8.21 (s, 1H), 2.59 (s, 1H); MS: 212 (M+l).

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, 1186608-73-0, 3-Methyl-1H-pyrazolo[3,4-b]pyridin-5-amine.

Reference:
Patent; ARRIEN PHARMAEUTICALS LLC; VANKAYALAPATI, Hariprasad; APPALANENI, Rajendra, P.; REDDY, Y., Venkata Krishna; WO2012/135631; (2012); A1;,
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. 915006-52-9, name is 6-Bromo-2-iodopyridin-3-amine, the common compound, a new synthetic route is introduced below. Application In Synthesis of 6-Bromo-2-iodopyridin-3-amine

To a mixture of 6-bromo-2-iodopyridin-3-amine (100 mg, 0.34 mmol), 1,2-dimethoxy-4-(prop-1-yn-1-yl)benzene (74 mg, 0.42 mmol), lithium chloride (18 mg, 0.42 mmol), sodium carbonate (180 mg, 1.68 mmol) and Pd(dppf)Cl2 (12.5 mg, 0.017 mmol) in a screw cap vial was added DMF (2 mL). The vial was fitted with a Teflon-lined septum cap. The system was evacuated under vacuum (via a needle from a nitrogen/vacuum manifold line) and backfilled with nitrogen gas. The procedure was repeated three times. The needle was removed and the vial was heated at 100 C. for 16 h. LCMS analysis shows formation of two isomers, in approximately 3:1 ratio. 1H NMR analysis suggested the major product to be 5-bromo-2-(3,4-dimethoxyphenyl)-3-methyl-1H-pyrrolo[3,2-b]pyridine (5A-1). The reaction mixture was diluted with EtOAc (50 mL), poured into a separatory funnel and washed with 10% aqueous LiCl solution (2*10 mL) and saturated aqueous NaCl solution (10 mL), dried (Na2SO4), filtered and the filtrate was concentrated. The crude product was dissolved in a small amount of DCM and purified on a silica gel column chromatography with a 15 min gradient from 0%-100% DCM/EtOAc to afford 5-bromo-2-(3,4-dimethoxyphenyl)-3-methyl-1H-pyrrolo[3,2-b]pyridine (Intermediate 5A-1) that was contaminated with Intermediate 5A-2, 5-bromo-3-(3,4-dimethoxyphenyl)-2-methyl-1H-pyrrolo[3,2-b]pyridine, m/z (303, M+1), 80 mg (67%). To a mixture containing 5-bromo-2-(3,4-dimethoxyphenyl)-3-methyl-1H-pyrrolo[3,2-b]pyridine (Intermediate 5A-1) and Intermediate 5A-2 (100 mg, 0.29 mmol), tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridine-1 (2H)-carboxylate (111 mg, 0.36 mmol), and Pd(dppf)C12 (10.5 mg, 0.014 mmol) in a screw cap vial was added THF (2.5 mL) followed by 3M aqueous solution of tripotassium phosphate (0.10 mL, 0.3 mmol). The vial was fitted with a Teflon lined septum cap. The system was evacuated under vacuum (via a needle from a nitrogen/vacuum manifold line) and backfilled with nitrogen gas. The procedure was repeated three times. The needle was removed and the vial was heated at 75 C. for 3 h. The reaction mixture was cooled to room temperature and treated with saturated aqueous NaCl solution (5 mL) and extracted with ethyl acetate (3*10 mL). The extracts were combined, dried (Na2SO4), filtered and concentrated. The crude product was dissolved in a small amount of DCM and purified on silica gel column chromatography eluting with a 10 min gradient from 5%-100% DCM/EtOAc. No separation was observed. A mixture of tert-butyl 4-(2-(3,4-dimethoxyphenyl)-3-methyl-1H-pyrrolo[3,2-b]pyridin-5-yl)-5,6-dihydropyridine-1(2H)-carboxylate (Intermediate 5B) and the regioisomer tert-butyl 4-(3-(3,4-dimethoxyphenyl)-2-methyl-1H-pyrrolo[3,2-b]pyridin-5-yl)-5,6-dihydropyridine-1 (2H)-carboxylate was isolated (100 mg, 77% yield), m/z (550, M+1) and was used as such in subsequent step. A mixture of tert-butyl 4-(2-(3,4-dimethoxyphenyl)-3-methyl-1H-pyrrolo[3,2-b]pyridin-5-yl)-5,6-dihydropyridine-1(2H)-carboxylate (Intermediate 5B) and regioisomer tert-butyl 4-(3-(3,4-dimethoxyphenyl)-2-methyl-1H-pyrrolo[3,2-b]pyridin-5-yl)-5,6-dihydropyridine-1(2H)-carboxylate (95 mg, 0.21 mmol) was dissolved in MeOH (5 mL) and transferred to a Parr bottle. The mixture was purged with nitrogen. Pearlman’s Catalyst (25 mg, 0.036 mmol) was added and the bottle was pressurized with hydrogen gas (50 psi) and shaken for 22 h. The reaction mixture was filtered through a pad of Celite and the filtrate was concentrated. The resulting residue was dissolved in a small amount of DCM and charged to a silica gel column, which was eluted over a 10 min gradient with 1%-5% MeOH/DCM to afford a mixture of tert-butyl 4-(2-(3,4-dimethoxyphenyl)-3-methyl-1H-pyrrolo[3,2-b]pyridin-5-yl)-5,6-dihydropyridine-1(2H)-carboxylate (Intermediate 5C) and the regioisomer tert-butyl 4-(3-(3,4-dimethoxyphenyl)-2-methyl-1H-pyrrolo[3,2-b]pyridin-5-yl)-5,6-dihydropyridine-1 (2H)-carboxylate (82 mg, 80%), m/z (452, M+H).

The synthetic route of 915006-52-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; Dyckman, Alaric J.; Dodd, Dharmpal S.; Mussari, Christopher P.; Sherwood, Trevor C.; Whiteley, Brian K.; Gilmore, John L.; Kumar, Sreekantha Ratna; Pasunoori, Laxman; Srinivas, Pitani Veera Venkata; Duraisamy, Srinivasan Kunchithapatham; Hegde, Subramanya; Anumula, Rushith Kumar; US2019/185469; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem