Category: pyridine-derivatives

Application of 78846-88-5, 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.78846-88-5, name is 2-Chloro-6-(chloromethyl)pyridine, molecular formula is C6H5Cl2N, molecular weight is 162.0166, as common compound, the synthetic route is as follows.

Building block G72: 2-chloro-6-(methoxymethyl)pyridine; To a solution of 2-chloro-6-(chloromethyl)pyridine (120 mg, 0.70 mmol) in anhydrous MeOH (3 ml) was added sodium methoxide (82 mg, 1.5 mmol) under argon. The reaction mixture was stirred at 50 C. for 24 h. The reaction mixture was quenched with water and extracted with dichloromethane. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to afford the title compound as a colorless oil [1H NMR (400 MHz, DMSO-d6) delta ppm 7.85 (t, J=7.8 Hz, 1H), 7.40 (d, J=7.8 Hz, 1H), 7.39 (d, J=7.8 Hz, 1H), 4.44 (s, 2H), 3.34 (s, 3H)].

Statistics shows that 78846-88-5 is playing an increasingly important role. we look forward to future research findings about 2-Chloro-6-(chloromethyl)pyridine.

Reference:
Patent; BADIGER, Sangamesh; BEHNKE, Dirk; BETSCHART, Claudia; COTESTA, Simona; HINTERMANN, Samuel; OFNER, Silvio; PANDIT, Chetan; ROY, Bernard Lucien; US2012/101110; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 26218-75-7, 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.26218-75-7, name is Methyl 6-bromopicolinate, molecular formula is C7H6BrNO2, molecular weight is 216.03, as common compound, the synthetic route is as follows.

Into a 2000-mL 4-necked round- bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed methyl 6-bromopyridine-2-carboxylate (43.2 g, 199.97 mmol, 1.00 equiv), tetrahydrofuran (700 mL). This was followed by the addition of bromo(methyl)magnesium (150 mL) dropwise with stirring at 0C. The resulting solution was stirred overnight at room temperature. The mixture was then quenched by the addition of 200 mL of water. The resulting solution was extracted with 3×200 mL of ethyl acetate and the organic layers combined. The resulting mixture was washed with 2×200 mL of brine. The mixture was dried over anhydrous sodium sulfate and concentrated under vacuum. This resulted in 35 g (81%) of 2-(6-bromopyridin-2-yl)propan-2- ol as yellow oil.

The chemical industry reduces the impact on the environment during synthesis 26218-75-7, I believe this compound will play a more active role in future production and life.

Reference:
Patent; NEWAVE PHARMACEUTICAL INC.; CHEN, Yi; (0 pag.)WO2019/165204; (2019); 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. 58584-63-7, name is (6-Methoxypyridin-3-yl)methanol, the common compound, a new synthetic route is introduced below. Safety of (6-Methoxypyridin-3-yl)methanol

j0259j To a stirred solution of (6-methoxypyridin-3-yl)methanol (75 mg, 0.54 mmol) in dichloromethane (2 mL) under nitrogen was added triethylamine (0.083 mL, 0.59 mmol) followed by methanesulfonyl chloride (0.044 mL, 0.57 mmol). The mixture was stirred at room temperature for 1 hour. The mixture was partitioned between dichioromethane (10 mL) and water (10 mL). The organic extract was dried over sodium sulfate, filtered and concentrated to give the title compound 88 mg (quantitative yield) as a yellow oil.Tr(METCR1278) = 1.63 mm, (ESj (M-J-H) 1581160.

The synthetic route of 58584-63-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CHDI FOUNDATION, INC.; DOMINGUEZ, Celia; WITYAK, John; BARD, Jonathan; KISELYOV, Alex; BROWN, Christopher, John; GALAN, Sebastien, Rene Gabriel; PRIME, Michael, Edward; GILES, Paul, Richard; GADOULEAU, Elise, Luciennen Paulette; KRUeLLE, Thomas, Martin; CLARK-FREW, Daniel; JOHNSON, Peter, David; SCHAERTL, Sabine; HERRMANN, Frank; GRIMM, Steffen, Kaspar; KAHMANN, Jan, Dirk; SCHEICH, Christoph; COE, Samuel; HAYES, Sarah; (271 pag.)WO2016/33445; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 866545-96-2, 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 866545-96-2, name is 1-(5-Bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)ethanone. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of l-(5-bromo-lH-pyrrolo[2,3-b]pyridin-3-yl)ethanone (50 g, 0.21 mol) in tetrahydrofuran (1400 mL) was added sodium hydride (8.8 g, 0.22 mol, 60 %) at 0 C. After the mixture was stirred for 1 h at 0 C a solution of 4-methylbenzene-l-sulfonyl chloride (48.3 g, 0.25 mol) in tetrahydrofuran (300 mL) was added dropwise at 0 C. The resulting mixture was warmed up to RT and stirred overnight. The reaction mixture was poured into ice water and extracted with ethyl acetate (3 xlOOO mL). The combined organic layers were washed with brine, dried over sodium sulfate and concentrated to dryness in vacuo affording crude l-(5-bromo-l-tosyl-lH-pyrrolo[2,3-b]pyridin-3-yl)ethanone as yellow solid (75 g, yield: 90 %), which was used for the next step without further purification: NMR (400 MHz, DMSO-d6): delta 8.884 (s, 1H), 8.532-8.573 (m, 2H), 8.054-8.075 (d, J = 12 Hz, 2H), 7.442-7.463 (d, J = 8.4 Hz, 2H), 2.578 (s, 3H), 2.347 (s, 3H

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 866545-96-2, 1-(5-Bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)ethanone.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; ESTRADA, Anthony; LIU, Wen; PATEL, Snahel; SIU, Michael; WO2014/111496; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 110651-92-8, 7-Chloro-6-nitrothieno[3,2-b]pyridine, 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, Formula: C7H3ClN2O2S, blongs to pyridine-derivatives compound. Formula: C7H3ClN2O2S

A mixture of 7-chloro-6-nitrothieno[3,2-b]pyridine (0.055 g, 0.26 mmol) (Example 1, Step 2), cyclohexanamine (59 muL, 0.51 mmol) and N,N-diisopropylethylamine (0.13 mL, 0.77 mmol) in isopropyl alcohol (0.87 mL) was heated at 90 C. for 2 h. The resulting mixture was concentrated to give the desired product, which was used directly in the next step. LCMS calculated for C13H16N3O2S (M+H)+: m/z=278.1. Found: 278.0.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,110651-92-8, 7-Chloro-6-nitrothieno[3,2-b]pyridine, and friends who are interested can also refer to it.

Reference:
Patent; Incyte Corporation; Li, Yun-Long; Zhu, Wenyu; Mei, Song; Glenn, Joseph; US2014/121198; (2014); 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.189005-44-5, name is 6-Methyl-2-(4-methylphenyl)imidazol[1,2-a]pyridine-3-acetic acid, molecular formula is C17H16N2O2, molecular weight is 280.3211, as common compound, the synthetic route is as follows.COA of Formula: C17H16N2O2

One proceeds as described in Example 2 except that methanolic hydrogen chloride is replaced by 5.0 g of p -toluene-sulfonic acid catalyst and the reaction mixture is heated to boiling for 6 hours. The crystalline product is recrystallized from acetonitrile. Thus 22.2 g of methyl-[6-methyl-2-(4-methyl-phenyl)-imidazo[1,2-a]pyridine-3-yl]-acetate are obtained, yield 75.6 %. The product is identical in all respects with the compound prepared according to Example 1.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,189005-44-5, 6-Methyl-2-(4-methylphenyl)imidazol[1,2-a]pyridine-3-acetic acid, and friends who are interested can also refer to it.

Reference:
Patent; EGIS GYOGYSZERGYAR RT.; EP1259509; (2005); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 88912-27-0 ,Some common heterocyclic compound, 88912-27-0, molecular formula is C6H4ClNO2, 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.

Reference Production Example 36A mixture of 0.50 g of 2-amino-5-chloro-4-trifluoromethylphenol, 0.36 g of 3- chloroisonicotinic acid, 0.56 g of WSC and 5 ml of pyridine was stirred while heating at 80C for three hours. The reaction mixture was cooled to room temperature, and then water was added, followed by extraction with ethyl acetate three times. The combined organic layers were washed with water and a saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 0.46 g of 3-chloro-N-[4-chloro-2- hydroxy-5-trifluoromethylphenyl]isonicotinamide.1 H-NMR (DMSO-de) delta: 10.32 (br s, IH), 8.75 (s, IH), 8.64 (d, J=4.8 Hz, IH), 8.43 (s, 7.63 (d, J=4.8 Hz, IH), 7.13 (s, IH)

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. 88912-27-0, 3-Chloroisonicotinic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SUMITOMO CHEMICAL COMPANY, LIMITED; OTSUKI, Junko; WO2011/40629; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 609-70-1, 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. 609-70-1, name is 4-Hydroxynicotinic acid, molecular formula is C6H5NO3, 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 4-hydroxynicotinic acid (2.00 g, 14.4 mmol) in DMF (30 mL) is added sodium hydride (0.62 g, 55% dispersion in mineral oil, 14.2 mmol). After stirring for 10 min at room temperature, 4-cyanobenzyl bromide (2.88 g, 14.7 mmol) is added. After stirring for 2 h at room temperature, DMF (15 mL) is added and the reaction mixture is diluted with water. The formed precipitate is filtered off and dried. Yield: 2.57 g (56% of theory); ESI mass spectrum: [M+H]+=255; Retention time HPLC: 0.68 min (Z002-002).

According to the analysis of related databases, 609-70-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; OOST, Thorsten; FIEGEN, Dennnis; GNAMM, Christian; HANDSCHUH, Sandra; PETERS, Stefan; ROTH, Gerald Juergen; US2014/57916; (2014); 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. 58584-86-4, name is Ethyl 2,6-dichloronicotinate, molecular formula is C8H7Cl2NO2, 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. SDS of cas: 58584-86-4

Production Example 7 1.00 g of ethyl 2,6-dichloronicotinate was dissolved in 10 mL of methylene chloride, and 1.05 g of sodium methoxide (28 wt% of methanol solution) was added thereto at room temperature. After stirring at room temperature for 2 days, the reaction mixture was concentrated, and the residue was purified by silica gel column chromatography (hexane-ethyl acetate) to obtain 511 mg of methyl 6-chloro-2-methoxynicotinate as a white solid.

With the rapid development of chemical substances, we look forward to future research findings about 58584-86-4.

Reference:
Patent; Astellas Pharma Inc.; EP2085383; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 147269-67-8 , The common heterocyclic compound, 147269-67-8, name is Benzyl (2-oxo-1,2-dihydropyridin-3-yl)carbamate, molecular formula is C13H12N2O3, 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 stirred solution of benzyl (2-oxo-1,2-dihydropyridin-3-yl)carbamate (3.17 g, 12.96 mmol) in 1,4-dioxane (150 mL) under nitrogen atmosphere, NaH (0.5 19 g, 12.96 mmol) was added and kept stir at rt for 10 mi 2-chloro-5-fluoro-4-methylpyrimidine (1.9 g, 12.96 mmol) was added and heated in a pressure tube at 110 C for 24h. Thereaction mixture was concentrated under vacuum to remove the solvent. To the crude resiude was extracted with EtOAc (50 mL) and water (50 mL). The aq. layer was further extracted with EtOAc (3 x 5OmL) and the combined organic layer was washed with brine (50 mL), dried over sodium sulfate. The desired product benzyl (1-(5-fluoro-4- methylpyrimidin-2-yl)-2-oxo- 1 ,2-dihydropyridin-3 -yl)carbamate (300 mg, 0.820 mmol,6.32 % yield) was isolated as a brown solid by ISCO (24g silica gel, solid loading, 40-100% ethyl acetate/pet ether).

The synthetic route of 147269-67-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; LIU, Chunjian; LIN, James; MOSLIN, Ryan M.; WEINSTEIN, David S.; TOKARSKI, John S.; WO2015/89143; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem