Month: July 2021

Electric Literature of 5350-93-6, 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.5350-93-6, name is 6-Chloropyridin-3-amine, molecular formula is C5H5ClN2, molecular weight is 128.56, as common compound, the synthetic route is as follows.

A solution of 5-amino-2-chIoropyridine (30.94 g, 236 mmol) and di-tert-butyldicarbonate (65.36 g, 299 mmol) in 1 ,4-dioxane (300 ml.) was stirred at reflux for 20 hours. Additional di- tert-butyldicarbonate (8.30 g, 38 mmol) was added and the reaction was stirred at reflux for 7 hours. The reaction was cooled to room temperature and poured into water. The Jayers were separated and the aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with brine, dried over magnesium sulfate, and solvent was removed at reduced pressure to give a brown oil. The oil was triturated with diethyl ether and filtered to give tert-butyl 6-chloropyridin-3-ylcarbamate as a tan solid. (49.84 g, 92% yield). 1H NMR (CDCI3) delta 8.24 (m, 1 H)1 7.96 (m, 1 H), 7.27 (m, 1 H), 6.65 (br s, 1 H), 1.51 (s, 9H).

The chemical industry reduces the impact on the environment during synthesis 5350-93-6, I believe this compound will play a more active role in future production and life.

Reference:
Patent; PHARMACIA & UPJOHN COMPANY LLC; WO2006/126083; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1480-64-4, 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 1480-64-4, name is 3-Chloro-2-fluoropyridine. This compound has unique chemical properties. The synthetic route is as follows.

3-Chloro-2-fluoropyridine (5.00 g, 37.25 mmol, 1 eq.) and benzylamine (5.75 mL, 52.15 mmol, 1.4 eq.) were addedto cesium carbonate (18.21 g, 55.88 mmol, 1.5 eq.) in dimethyl sulfoxide (25 mL) and the reaction mixture wasstirred at 105 C for 7 h. After cooling to 25 C water (25 mL) was added dropwise using an ice bath to maintain thetemperature below 30C. The reaction mixture was transferred to a separation funnel. Then water (15 mL) andethyl acetate (40 mL) were added and the phases were separated. The aqueous phase was extracted with ethylacetate (2 x 50 mL). The combined organic phases were washed with water (4 x 50 mL) and brine (50 mL). Dryingover magnesium sulfate, removal of the solvent and purification by flash chromatography (2 to 3% ethyl acetate inheptanes) gave the N-benzyl-3-chloropyridin-2-amine as a white solid (6.56 g, 81%). Rf = 0.25 (5% ethyl acetate inheptanes).1H NMR (400 MHz, CDCl3): = 1H NMR (400 MHz, CDCl3): = 4.71 (d, J = 5.5 Hz, 2 H), 5.28 (br. s, 1 H), 6.57 (dd, J =7.8, 5.0 Hz, 1 H), 7.27 – 7.32 (m, 1 H), 7.33 – 7.42 (m, 4 H), 7.46 -7.51 (obs. m, 1 H), 8.07 (dd, J = 4.9, 1.6 Hz, 1 H).13C NMR (101 MHz, CDCl3): = 45.5, 113.1, 115.4, 127.3, 127.7, 128.6, 136.1, 139.3, 146.0, 153.9.LC/MS (m/z): [M + H]+ calculated for C12H12ClN2+, 219.1 ; found, 218.7

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 1480-64-4, 3-Chloro-2-fluoropyridine.

Reference:
Article; De Gasparo, Raoul; Lustenberger, Philipp; Mathes, Christian; Schlama, Thierry; Veitch, Gemma E.; Le Paih, Jacques J. M.; Synlett; vol. 26; 2; (2015); p. 197 – 200;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 5470-17-7 , The common heterocyclic compound, 5470-17-7, name is 3-Bromo-2-chloro-5-nitropyridine, molecular formula is C5H2BrClN2O2, 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.

Step 1: 2-(3-bromo-5-nitropyridin-2-yloxy)-N, N-dimethylethanamine (Intermediatell).To a stirred solution of S-bromo-l-chloro-S-nitropyridine (2.5 g, 10.53 mmol) and 2-(dimethylamino) ethanol (1.877 g, 21.06 mmol) in DMF (10 mL) was added portion wise potassium carbonate (2.91 g, 21.06 mmol) and the mixture was stirred at 60 0C for 2- 3 hrs. Reaction mixture was cooled to RT, diluted with ethyl acetate (50-7OmI), washed with water and then brine, organic layer was collected, dried over sodium sulfate and concentrated in vacuo to give crude 2-(3-bromo-5-nitropyridin-2-yloxy)-N, N- dimethylethanamine (2.70 g, 88 %) as brown liquid. The crude material was taken for next step without further purification. MS (ES+): 292 for C9H12BrN3O3

The synthetic route of 5470-17-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2009/147431; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 157402-44-3, 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 157402-44-3, name is 6-Phenylpicolinaldehyde. This compound has unique chemical properties. The synthetic route is as follows.

To a vigorously-stirred solution of 6-phenyl-2-pyridine aldehyde (0.50 g, 2.73 mmol) in 30 ml_ of anhydrous Et2O under N2, was added a solution of benzylmagnesium chloride (3 ml_ of 1 M solution in Et2O, 3.0 mmol) at ambient temperature. After 12 h, the reaction was quenched with 5 ml_ saturated aqueous ammonium chloride. This solution was extracted with 3 x 10 ml_ EtOAc. The organic fractions were pooled, dried over Na2SO4 and concentrated. After removing the volatiles in vacuo, the resultant yellow oil was chromatographed on silica with 10% EtOAc/hexanes. Clean fractions were combined and the volatiles were removed to provide 0.31 g of the alcohol intermediate as a yellow oil (41 %).

According to the analysis of related databases, 157402-44-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; EXXONMOBIL CHEMICAL PATENTS INC.; WO2008/85659; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 54916-66-4, 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. 54916-66-4, name is 5-Bromo-2-methoxynicotinic acid. A new synthetic method of this compound is introduced below.

5-Bromo-2-methoxynicotinic acid (15 g, 64.6 mmol, commercially available from, for example Apollo Scientific) was suspended in DCM (100 mL) and then oxalyl chloride (16.98 mL, 194 mmol) was added, followed by DMF (5.01 mL, 64.6 mmol) and the mixture was stirred for 18 h at rt. The solvent was evaporated in vacuo and the residue was redissolved in DCM (100 mL) and evaporated to dryness to give 5-bromo-2-methoxynicotinoyl chloride (16.33 g, 65.2 mmol, 101 % yield) which was used in the next step immediately. (0454) *H NMR (400 MHz, CDCI3) delta ppm 8.49 (d, J=2.7 Hz, 1 H) 8.44 (d, J=2.4 Hz, 1 H) 4.06 (s, 3 (0455) H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,54916-66-4, 5-Bromo-2-methoxynicotinic acid, and friends who are interested can also refer to it.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; ATKINSON, Stephen, John; DEMONT, Emmanuel, Hubert; HARRISON, Lee, Andrew; HAYHOW, Thomas, George, Christopher; LINDON, Matthew, J.; PRESTON, Alexander, G.; SEAL, Jonathan, Thomas; WALL, Ian, David; WATSON, Robert, J.; WOOLVEN, James, Michael; (91 pag.)WO2017/60180; (2017); 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. 17920-35-3, name is 2-Amino-6-methoxypyridine, the common compound, a new synthetic route is introduced below. Quality Control of 2-Amino-6-methoxypyridine

A solution of 5-(2-(trifluoromethyl)phenyl)pyrazolo[1,5-a]pyrimidine-3-carbonyl chloride (254.0 mg, 0.75 mmol) and 6-methoxypyridine-2-amine (136.0 mg, 1.10 mmol) in pyridine (10 mL) was stirred for 2 h at 50 °C. The reaction mixture was poured into H2O and the solid was collected by filtration. The crude residue was purified by flash chromatography to give N-(6-methoxypyridin-2-yl)-2-methyl-5-(2-(trifluoromethyl)phenyl)pyrazolo[1,5-a]pyrimidine-3-carboxamide (85.0 mg, 27percent yield). MS (ESI) calcd for C21H16F3N5O2 (m/z): 427.13; found: 428 [M+H

The synthetic route of 17920-35-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GlaxoSmithKline LLC; CASAUBON, Rebecca, L.; NARAYAN, Radha; OALMANN, Christopher; VU, Chi, B.; (583 pag.)EP2768509; (2017); B1;,
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. 37669-64-0, name is 5-Bromo-3-pyridinemethanol. This compound has unique chemical properties. The synthetic route is as follows. HPLC of Formula: C6H6BrNO

To a solution of (5-bromopyridin-3-yl)methanol (3 g, 16.0 mmol) in DCM (15 mL) cooled to 0 C was added thionylchloride (7.59 g, 63.8 mmol) dropwise and the reaction mixture was stirred at room temperature over night. The mixture was poured onto ice/water (20 mL), basified with NaOH cone. (8 mL) and extracted with EtOAc (2 x 50 mL). Combined organics were dried over Na2S04, filtered and evaporated to dryness. The residue was purified by silica gel flash chromatography eluting with a 0 to 40% EtO Ac-heptane gradient to give the title compound (3.08 g, 93 %) as a white solid. MS: 206.0, 207.9 (M+H+).

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, 37669-64-0, 5-Bromo-3-pyridinemethanol.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; AEBI, Johannes; AMREIN, Kurt; CHEN, Wenming; HORNSPERGER, Benoit; KUHN, Bernd; LIU, Yongfu; MAERKI, Hans P.; MAYWEG, Alexander V.; MOHR, Peter; TAN, Xuefei; WANG, Zhanguo; ZHOU, Mingwei; WO2013/79452; (2013); 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. 80194-68-9, name is 3-Chloro-5-(trifluoromethyl)picolinic acid, the common compound, a new synthetic route is introduced below. Formula: C7H3ClF3NO2

Example 187 N-(3-((4S,6S)-2-amino-4-methyl-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-4-yl)-4,5-difluorophenyl)-3-chloro-5-(trifluoromethyl)picolinamide The title compound was synthesized by procedures and steps analogous to those described in Method Z, Example 186 above, but using 3-chloro-5-(trifluoromethyl)-2-pyridine carboxylic acid (Bionet Research). MS m/z=517.1 [M+H]+. Calculated for C19H13ClF8N4O2: 516.77 1H NMR (300 MHz, CHLOROFORM-d) delta=9.82 (br. s., 1H), 8.77 (s, 1H), 8.22-8.08 (m, 2H), 7.10-7.00 (m, 1H), 4.37 (br. s., 2H), 4.04 (dd, J=5.3, 9.7 Hz, 1H), 2.86-2.70 (m, 1H), 1.91 (t, J=13.2 Hz, 1H), 1.64 (s, 3H)

The synthetic route of 80194-68-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MINATTI, Ana Elena; LOW, Jonathan D.; ALLEN, Jennifer R.; CHEN, Jian; CHEN, Ning; CHENG, Yuan; JUDD, Ted; LIU, Qingyian; LOPEZ, Patricia; QIAN, Wenyuan; RUMFELT, Shannon; RZASA, Robert M.; TAMAYO, Nuria A.; XUE, Qiufen; YANG, Bryant; ZHONG, Wenge; US2014/249104; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 17228-69-2, 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. 17228-69-2, name is 2-Chloro-4-methoxypyridine. A new synthetic method of this compound is introduced below.

To a solution of 2-chloro-4-methoxypyridine (10.0 g, 69.7 mmol) in 50 mL of sulfuric acid at 0C was added NBS. The reaction mixture was allowed to stir and warm up to room temperature for 2 h and then heated at 60C for 5 h. Next, the reaction mixture was cooled to room temperature, neutralized with 1 N NaOH (pH 7), diluted with water (50 ml) and the aqueous layer was extracted with ethyl acetate (2 x 100 mL).The organic layers were washed with water (2 x 50 mL), saturated NaHCO3, brine, dried over Mg2SO4 and concentrated to provide an oil, which was chromatographed to give 5-bromo-2- chloro-4-methoxypyridine eluting with 0-25% EtOAc/hexanes. ?HNMR (500 MHz, DMSO-d6) oe 8.4 (s, 1H), 7.29 (s, 1H), 3.97 (s, 3H); LC/MS: [(M+1)] = 223.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,17228-69-2, 2-Chloro-4-methoxypyridine, and friends who are interested can also refer to it.

Reference:
Patent; MERCK SHARP & DOHME CORP.; PASTERNAK, Alexander; PIO, Barbara; CHOBANIAN, Harry, R.; SHI, Zhi-Cai; DONG, Shuzhi; GUO, Yan; WALSH, Shawn, P.; GUO, Zhiqiang; FERGUSON, Ronald, D.; CATO, Brian; (114 pag.)WO2016/60941; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 944896-42-8 , The common heterocyclic compound, 944896-42-8, name is 6-Bromoimidazo[1,2-a]pyridine-3-carboxylic acid, molecular formula is C8H5BrN2O2, 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 6-bromoimidazo[l,2-a]pyridine-3-carboxylic acid (50 mg, 0.21 mmol) in DMF (0.5 mL) was added 3-methoxybenzylamine (37 mg, 0.27 mmol) and HATU (95 mg, 0.25 mmol). The resulting mixture was stirred at room temperature overnight. After removal of solvent by rotary evaporation, the residue was dissolved in ethyl acetate (15 mL) and washed with a saturated aqueous Na2C03 solution (2 x 10 mL), and brine (10 mL), dried over Na2S04, and filtered. The solvent was removed in vacuo and the crude amide product was purified by flash chromatography on silica gel to afford the title compound (52 mg, 70%). LC-MS: single peak at 254 nm, MH+ calcd. for C16H15BrN302: 360, obtained: 360.

The synthetic route of 944896-42-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FENG, Yangbo; CHEN, Yen Ting; SESSIONS, Hampton; MISHRA, Jitendra K.; CHOWDHURY, Sarwat; YIN, Yan; LOGRASSO, Philip; LUO, Jun-Li; BANNISTER, Thomas; SCHROETER, Thomas; WO2011/50245; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem