Day: November 5, 2020

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. 1003-68-5, name is 5-Methylpyridin-2(1H)-one. A new synthetic method of this compound is introduced below., 1003-68-5

EXAMPLE 4 5-Methyl-1-p-tolyl-2-(1H)-pyridone The reaction of p-iodotoluene with 5-methyl-2-(1H)-pyridone by the reaction of Example 1, affords 5-Methyl-1-p-tolyl-2-(1H)-pyridone in 89% yield.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1003-68-5, 5-Methylpyridin-2(1H)-one, and friends who are interested can also refer to it.

Reference:
Patent; Affiliated Medical Research, Inc.; US3974281; (1976); A;,
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 609-71-2, name is 2-Oxo-1,2-dihydropyridine-3-carboxylic acid. This compound has unique chemical properties. The synthetic route is as follows. 609-71-2

Commercial available 2-hydroxynicotinic acid (1.5 ?g, 10.78? mmol) was dissolved in anhydrous DMF (20.0 ?mL) and then NaH (650.0 ?mg, 27.08 ?mmol) was slowly added. After 1?h?at room temperature, p-fluorobenzyl chloride (1.5 mL, 12.52?mmol) was added and the reaction mixture was heated under stirring at 50?C for 12?h. After cooling to room temperature, the reaction mixture was evaporated under reduced pressure affording a white solid that was treated with a solution of 10% NaOH (20.0? mL) and heated at reflux for 4?h. Then the mixture was cooled at room temperature and acidified with concentrated HCl until pH?=?1-2. The obtained solid was filtered under vacuum, washed with water and dried to afford pure compound 12 (2.6 ?g, yield: 96%). 1H NMR (400MHz, DMSO): delta 12.02 (bs, 1H, COOH), 8.42-8.47 (m, 2H, H4 and H6 Py) 7.22-7.50 (m, 4H, ArH), 6.83-6.80 (m, 1H, H5 Py), 5.34 (s, 2H, N-CH2).

Statistics shows that 609-71-2 is playing an increasingly important role. we look forward to future research findings about 2-Oxo-1,2-dihydropyridine-3-carboxylic acid.

Reference:
Article; Chicca, Andrea; Arena, Chiara; Bertini, Simone; Gado, Francesca; Ciaglia, Elena; Abate, Mario; Digiacomo, Maria; Lapillo, Margherita; Poli, Giulio; Bifulco, Maurizio; Macchia, Marco; Tuccinardi, Tiziano; Gertsch, Juerg; Manera, Clementina; European Journal of Medicinal Chemistry; vol. 154; (2018); p. 155 – 171;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

17368-12-6, 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. 17368-12-6, name is 2-Chloro-4-hydroxypyridine, molecular formula is C5H4ClNO, 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.

3-Bromo-2,4-dimethyl-6-nitropyridine (2.2 g, 9.5 mmol) and 2-chloro-4- hydroxypyridine (2.5 g, 19 mmol) were combined in DMA (10 mL) and the solution was sonicated and sparged with Ar for 10 min. K2CO3 (4.0 g, 29 mmol) was added and the reaction mixture was stirred at 100 C for 12 h. The reaction mixture was poured into water (200 mL) and the precipitated solids were isolated by filtration. The solids were washed with sat. K2CO3 (aq) (3 x 50 mL) and water (3 x 50 mL) and dried under high vacuum for 5 h. The crude product was purified by silica gel chromatography (EtOAc/hexanes) to afford 3-((2-chloropyridin-4-yl)oxy)- 2,4-dimethyl-6-nitropyridine (0.50 g, 19 %) as a brown solid. H NMR (400 MHz, DMSO-i: delta 8.33-8.30 (m, 2 H), 7.15 (d, J = 2.3 Hz, 1 H), 7.01 (dd, J = 5.8, 2.3 Hz, 1 H), 2.33 (s, 3 H), 2.23 (s, 3 H); MS (ESI) m/z: 280.0 (M+H+).

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. 17368-12-6, 2-Chloro-4-hydroxypyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; DECIPHERA PHARMACEUTICALS, LLC; BRANDT, Gary E. L.; TELIKEPALLI, Hanumaiah; CALDWELL, Timothy Malcolm; SAMARAKOON, Thiwanka; FLYNN, Daniel L.; KAUFMAN, Michael D.; WO2014/145023; (2014); 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. 626-64-2, name is Pyridin-4-ol, the common compound, a new synthetic route is introduced below. 626-64-2

Al.l 4-Etaydroxypyridine ( 40.Og, 0.42 mol ) was added portionwise to fuming nitric acid (140 ml) and sulfuric acid (500ml). The resulting mixture was heated to 1400C for 12 hours. The reaction mixture was cooled in an ice-bath and cautiously poured onto ice (500ml). The yellow solid which precipitated was collected by filtration and dried under vacuum to yield Al.l ( 70.Og, 90%). 1H-NMR ( DMSO-d6) 6: 4.06 ( 2H, s). HPLC (B): 98.9%, ret. time = 0.173 min., LC/MS (M-H)+ = 184.

Statistics shows that 626-64-2 is playing an increasingly important role. we look forward to future research findings about Pyridin-4-ol.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2006/53166; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 5350-93-6, 6-Chloropyridin-3-amine, 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, 5350-93-6, blongs to pyridine-derivatives compound. 5350-93-6

6-Chloro-pyridine-3-sulfonyl chloride; Sodium nitrite (3.45g, 0.05mol) was added portion wise to a stirred solution of 6- chloro-pyridin-3-ylamine (6.4g, 0.05mol) in acetic acid (56ml) and HCl (cone) (9.92ml) while maintaining the temperature below 15¡ãC. This solution was then added drop wise to a stirred solution of sulfur dioxide (17.2g, 0.27mol), copper (II) chloride (1.85g, 0.01 lmol) and water (2.2ml) in acetic acid (37ml) at 5¡ãC. The reaction mixture was allowed to warm to room temperature and poured over ice water and stirred for a further 15min. The resultant precipitate was collected by filtration, washed with water and dried overnight in a vacuum oven to give 6- chloro-pyridine-3-sulfonyl chloride (6.41g, 60.5percent yield); (400 MHz; d6-DMSO) 8.54 (IH, d), 7.96 (IH, dd), 7.50 (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,5350-93-6, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; WO2008/138594; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 6419-36-9, 2-(Pyridin-3-yl)acetic acid hydrochloride, 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, 6419-36-9, blongs to pyridine-derivatives compound. 6419-36-9

HATU (41.6 mg, 0.11 mmol) was added to a solution of DIEA (0.048 mL, 0.27 mmol), 2-(pyridin-3-yl)acetic acid hydrochloride (18.98 mg, 0.11 mmol) and (R)-N-(3,5-difluoro-4-(2-methyl-1-oxo-1-(pyrrolidin-1-yl)propan-2-yl)phenyl)-6-methoxy-1,2,3,4-tetrahydroisoquinoline-1-carboxamide hydrochloride (45 mg, 0.09 mmol) in DMF (2 mL) at room temperature, and the mixture was stirred overnight at room temperature. To the reaction mixture was added aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, and dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (solvent gradient; 0?25% MeOH/ethyl acetate) to give the title compound (33.0 mg, 0.057 mmol, 62.8%) as a white solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,6419-36-9, its application will become more common.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; YAMAMOTO, SATOSHI; SHIRAI, JUNYA; WATANABE, HIROYUKI; FUKUMOTO, SHOJI; ODA, TSUNEO; TOKUHARA, HIDEKAZU; TOMATA, YOSHIHIDE; ISHII, NAOKI; TAWADA, MICHIKO; KOUNO, MITSUNORI; OCHIDA, ATSUKO; IMADA, TAKASHI; FUKASE, YOSHIYUKI; YUKAWA, TOMOYA; (719 pag.)TW2016/2105; (2016); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

1721-12-6, 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. 1721-12-6, name is 1-(2-Methylpyridin-3-yl)ethanone, molecular formula is C8H9NO, 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 B. 3-Chloroacetyl-2-methylpyridine hydrochloride. To 2.25 g (16.6 mmol) of the ketone from Step A dissolved in 20 mL of ethyl ether was added 20 mL of 1.0 M hydrogen chloride in ethyl ether, resulting in a pale yellow slurry. After 30 min, the precipitate was filtered and washed with ethyl ether. After drying in vacuo, 2.80 g (16.3 mmol) of a pale yellow powder was obtained. This material was dissolved in 15 mL of a solution of 1.0 M hydrogen chloride in acetic acid and treated with 2.18 g (16.3 mmol) of N-chlorosuccinimide. After six days, the reaction mixture was concentrated in vacuo, and the resultant pale yellow residue solidified on standing. This material was triturated with 20% acetic acid/ethyl ether, (3*50 mL) to afford 2.62 g of a white powder, 77% yield. The 1H NMR spectra of this compound appears as a rotameric mixture (65:35, rotamer A: rotamer B): 1H NMR (CDCl3) delta: 9.16, (d, J=2.0 Hz, 1H, rotamer A), 8.84, (dd, J=2.0, 8.4 Hz, 1H, rotamer A), 8.64, (d, J=2.0 Hz, 1H, rotamer B), 8.50, (dd, J=2.0, 8.4 Hz, 1H, rotamer B), 7.96, (d, J=8.4 Hz, 1H, rotamer A), 7.86, (d, J=8.4 Hz, 1H, rotamer B), 4.93, (s 1H, rotamer A), 3.74, (2d, J=11.8 Hz, 2H, rotamer B), 2.77, (s 1H, rotamer A), 2.72, (s 1H, rotamer B).

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. 1721-12-6, 1-(2-Methylpyridin-3-yl)ethanone, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Merck & Co., Inc.; US6291491; (2001); B1;,
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. 1003-68-5, name is 5-Methylpyridin-2(1H)-one. A new synthetic method of this compound is introduced below., 1003-68-5

A mixture of 5 -methyl- lH-pyridin-2-one (100 g), bromo benzene (259 g, comprising greater than 0.2% by weight dibromobenzene isomers) and dimethylformamide (200 ml) were added in to a round bottom flask and stirred up to complete dissolution. Potassium carbonate (254 g) and copper (I) chloride (18.2 g) was added to the above reaction mass and then heated to 130-140C. The reaction mass was stirred at 130-140C for 10 hrs. After the reaction completion, the reaction mass was cooled to 25-35C. Toluene (500 ml), aqueous sodium chloride (75 g of sodium chloride in 500 ml of water) was added to the reaction mass and stirred for 15-30 mins at 25-35C. The reaction mass was filtered and the filtrate was allowed to settle. Organic and aqueous layers were separated and the aqueous layer was extracted with toluene. Organic layers combined and was washed with aqueous sodium chloride, treated with carbon and filtered through hyflo. The solvent from the filtrate was distilled off completely under vacuum at below 60C. Toluene (300 ml) was added to the obtained residue and stirred for 30 mins. The reaction mass was heated to 77-83C and stirred for 45 mins. The reaction mass was cooled to 25-35C over 60 mins. The reaction mass was further cooled to 0-6C. The solid obtained was filtered, washed with toluene and dried under vacuum. DM water (500 ml) was added to the above obtained wet compound followed by 50% aqueous sodium hydroxide solution (10 g of sodium hydroxide in 20 ml of water) at 25-35C. The reaction mass was heated to 75-85C and stirred for 30-60 mins. The reaction mass was then gradually cooled to 25-35C and stirred for 60 mins. The reaction mass was further cooled to 0-5 C and stirred for 3 hrs. The obtained solid was filtered, washed with water and dried to provide the title compound.Yield: 120 g; purity by HPLC: 99%; The XRPD is set forth in Figure 1 The DSC is set forth in Figure 2.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1003-68-5, 5-Methylpyridin-2(1H)-one, and friends who are interested can also refer to it.

Reference:
Patent; LAURUS LABS LIMITED; BOLLU, Ravindra Babu; MANDADAPU, Venkata Pramod Kumar; INDUKURI, Venkata Sunil Kumar; CHAVA, Satyanarayana; (20 pag.)WO2017/122139; (2017); A1;,
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 586-95-8, name is 4-Pyridinemethanol. This compound has unique chemical properties. The synthetic route is as follows. 586-95-8

Dissolve 4-pyridinemethanol (200 mg, 1.83 mmol) in 2 ml of dichlorosulfoxide. After heating to 70 C. for 1 h, concentrate to remove dichlorosulfoxide under reduced pressure to obtain compound 39b

Statistics shows that 586-95-8 is playing an increasingly important role. we look forward to future research findings about 4-Pyridinemethanol.

Reference:
Patent; Sichuan University; Li Guobo; Wang Zhenling; (40 pag.)CN111187218; (2020); A;,
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. 117519-09-2, name is 3-Amino-2-chloro-6-(trifluoromethyl)pyridine. A new synthetic method of this compound is introduced below., 117519-09-2

A mixture of 2-chloro-6-(trifluoromethyl)pyridin-3-amine (5.0 g, 25.44 mmol), 4,4,5,5-tetramethyl-2-(prop-l-en-2-yl)-l,3,2-dioxaborolane (4.7 g, 27.98 mmol), Pd(dppf)Cl2 (1.86 g, 2.54 mmol) and K2C03 (8.79 g, 63.59 mmol) in l,4-dioxane (50 mL) and H20 (10 mL) was stirred at 80C for 7 hours under a nitrogen atmosphere. After cooling to room temperature, the reaction mixture was concentrated. The crude residue was purified by silica gel column chromatography (0-10% EtOAc in petroleum ether) to give 3-nitro-2-(prop-l-en-2-yl)-6- (trifluoromethyl)pyridine (4.68 g, yield: 91% ) as a light yellow solid. 1H NMR (400 MHz, CDCl3) d = 7.34, (d, J= 8.4 Hz, 1H), 7.03 (d, J= 8.4 Hz, 1H), 5.54-5.53 (m, 1H), 5.36-5.34 (m, 1H), 4.22 (s, 2H), 2.18 (s, 3H)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,117519-09-2, 3-Amino-2-chloro-6-(trifluoromethyl)pyridine, and friends who are interested can also refer to it.

Reference:
Patent; GENENTECH, INC.; STAFFORD, Jeffrey, A.; VEAL, James, M.; TRZOSS, Lynnie, Lin; MCBRIDE, Christopher; PASTOR, Richard, M.; STABEN, Steven, Thomas; STIVALA, Craig; VOLGRAF, Matthew; (200 pag.)WO2020/18970; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem