Month: April 2022

Electric Literature of 77145-64-3, Adding some certain compound to certain chemical reactions, such as: 77145-64-3, name is 2-Chloro-6-(methylthio)pyridine,molecular formula is C6H6ClNS, 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 77145-64-3.

(Example 16) 2-chloro-6-methylthiopyridine (208 mg, 1.30 mmol) and N-chlorosuccinimide (17 mg, 0.13 mmol) were mixed with ethyl acetate (2 mL). 10% aqueous solution of sodium hypochlorite (2.2 g, 2.93 mmol) was added to the mixture at room temperature, and it was stirred for 1 hour. After that, ethyl acetate (10 mL) and sodium sulfite (164 mg, 1.30 mmol) were added to the mixture, and it was stirred. After stirring and separation, an organic layer was concentrated under reduced pressure, and the residue was subjected to purification by means of a silica gel column to obtain 2-chloro-6-methylsulfonylpyridine (244 mg, yield: 98 %).

According to the analysis of related databases, 77145-64-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Takeda Pharmaceutical Company Limited; EP2003116; (2008); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 19346-43-1, 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.19346-43-1, name is 2-Fluoro-3-nitro-4-picoline, molecular formula is C6H5FN2O2, molecular weight is 156.1145, as common compound, the synthetic route is as follows.

To 2-ethoxyethan-1 -amine (0.659 g, 7.40 mmol) in DMF (10 mL) were added 2-fluoro-4- methyl-3-nitropyridine (1 .05g, 6.73 mmol) and K2C03 (1 .022 g, 7.40 mmol), and the reaction mixture was stirred at room temperature overnight. The reaction was diluted with water (30 mL) and extracted with EtOAc (4 x 20 mL). The organic extracts were combined and washed with brine, dried over MgS04, filtered, and concentrated. Purification by chromatography on silica gel (0 to 30% EtOAc/hexanes) afforded N-(2-ethoxyethyl)-4- methyl-3-nitropyridin-2-amine (1 .52 g) as an orange color oil. LC-MS (ES) m/z = 226 [M+H]+. NMR (400 MHz, DMSO-c/6): 5 1 .1 1 (t, J =7.0 Hz, 3H), 2.39 (s, 3H), 3.46 (q, J = 6.8 Hz, 2H), 3.50 – 3.55 (m, 2H), 3.56 – 3.63 (m, 2H), 6.64 (d, J = 4.8 Hz, 1 H), 7.54 (t, J = 5.1 Hz, 1 H), 8.16 (d, J = 4.8 Hz, 1 H).

The chemical industry reduces the impact on the environment during synthesis 19346-43-1, I believe this compound will play a more active role in future production and life.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; MEDINA, Jesus Raul; TIAN, Xinrong; NG DI MARCO, Christina; GRAYBILL, Todd L.; HEERDING, Dirk A.; LI, William Hoi Hong; MANGATT, Biju; MARTYR, Cuthbert D.; RIVERO, Raphael Anthony; (570 pag.)WO2019/49061; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 582303-10-4 ,Some common heterocyclic compound, 582303-10-4, molecular formula is C8H11NO, 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 mixture of tri-n-butylphosphine (7.10 mL) , (2,6- dimethylpyridin-3-yl) methanol (3.00 g) , ethyl ( 6-hydroxy-l- benzothiophen-3-yl) acetate (5.43 g) and THF (150 mL) was added ADDP (7.17 g) at room temperature. The mixture was stirred at room temperature under nitrogen atmosphere overnight. The mixture was concentrated. To the residue was added IPE and the precipitate was filtered off. The filtrate was concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/hexane) to give the title compound (7.74 g) XH NMR (300 MHz, CDC13) 61.19-1.32 (3H, m) , 2.54 (3H, s), 2.58 (3H, s), 3.81 (2H, d, J = 0.8 Hz), 4.17 (2H, q, J = 7.2 Hz), 5.08 (2H, s), 7.02 (1H, d, J = 7.9 Hz), 7.08 (1H, dd, J = 8.7, 2.3 Hz), 7.19 (1H, t, J = 0.9 Hz), 7.39 (1H, d, J = 2.3 Hz), 7.61 (1H, d, J = 7.6 Hz), 7.67 (1H, d, J = 8.7 Hz).

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. 582303-10-4, (2,6-Dimethylpyridin-3-yl)methanol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; TAKAKURA, Nobuyuki; BANNO, Yoshihiro; TERAO, Yoshito; OCHIDA, Atsuko; MORIMOTO, Sachie; KITAMURA, Shuji; TOMATA, Yoshihide; YASUMA, Tsuneo; IKOMA, Minoru; MASUDA, Kei; WO2013/125732; (2013); A1;,
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. 98197-88-7, name is 2-(Hydroxymethyl)-4-nitropyridine. This compound has unique chemical properties. The synthetic route is as follows. Application In Synthesis of 2-(Hydroxymethyl)-4-nitropyridine

To a stirred solution of (4-nitro-2-pyridyl)methanol (3530 mg; 22.3 mmol)[CAS 98197-88-7] in N,N- dimethylformamide (60 mL) were added imidazole (3070 mg; 44.7 mmol) and teri-butyl-chloro- dimethyl-silane (4080 mg; 26.8 mmol) at 0 C. The reaction mixture was allowed to warm up naturally to room temperature and stirred for 18 hours. The reaction mixture was quenched with distilled water (30 mL) and the product was extracted with ethyl acetate (3 x 100 mL). The combined organic layers were washed with brine, dried over anhydrous Na2S04, filtered and concentrated to dryness. The residue was purified by column chromatography (silica gel; petroleum ether: ethyl acetate; 25: 1 ; v/v) to afford tert- butyl-dimethyl-[(4-nitro-2-pyridyl)methoxy]silane (5790 mg) as a light yellow oil. MS m/z (+ESI): 269.0 [M+H]+. ‘H-NMR (400 MHz, DMSO-O delta ppm: 8.89 (d, J= 5.2 Hz, 1H), 8.05 (d, J= 2.4 Hz, 1H), 8.01 (dd, Jl = 5.2 Hz, J2 = 2.4 Hz, 1H), 4.90 (s, 2H), 0.94 (s, 9H), 0.13 (s, 6H).

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, 98197-88-7, 2-(Hydroxymethyl)-4-nitropyridine.

Reference:
Patent; BASILEA PHARMACEUTICA INTERNATIONAL AG; LANE, Heidi; RICHALET, Florian; EL SHEMERLY, Mahmoud; (169 pag.)WO2018/2220; (2018); 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. 186413-75-2, name is 3-Bromo-6-chloro-2-methyl-5-nitropyridine, the common compound, a new synthetic route is introduced below. Product Details of 186413-75-2

Intermediate 4: S-Bromo-l-chloro–methyl-pyridin-S-ylamine In a 250ml RB flask, 3-bromo-6-chloro-2-methyl-5-nitropyridine (1.5 g, 5.97 mmol, commerical) was dissolved in ethyl acetate (20 mL). To this solution, ammonium chloride (3.19 g, 59.65 mmol) dissolved in water (10ml) was added and stirred at RT for 10 minutes. Then zinc powder (2.340 g, 35.79 mmol) was added at once and the resulting reaction mixture was refluxed at 550C for 6hrs. The reaction mixture was filtered through ceilite and concentrated in vacuo. The residue was partitioned between ethyl acetate (150ml) and water (75). The organic layer was dried over anhydrous sodium sulphate and concentrated in vacuo. The crude product was purified by Flash column chromatography using Argonaut purification system, which was eluted with 12% ethyl acetate in hexane to give 5-bromo-2-chloro-6-methylpyridin-3-amine (0.500 g, 37.8 %) as white solid. MS (ES+): 222 for C6H6BrClN2

The synthetic route of 186413-75-2 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 129432-25-3, 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 129432-25-3, name is 2,6-Dichloro-4-methylpyridin-3-amine. This compound has unique chemical properties. The synthetic route is as follows.

To a mixture of 2,6-dichloro-4-methylpyridin-3-amine (0.50 g, 2.8 mmol) and potassium thiocyanate (0.82 g, 8.5 mmol) in ethanol (7.5 mL) at room temperature was added concentrated hydrochloric acid (10.0 mL, 330 mmol) dropwise. The mixture was heated at 100 C for 44 h. Additional potassium thiocyanate (0.82 g, 8.5 mmol) was added, and the mixture was heated at 100 C for additional 31 h. The reaction mixture was cooledto room temperature and concentrated under vacuum to dryness. To the residue was added 1N aqueous NaOH (10 mL) followed by solid K2C03 until the mixture became basic (pH =9-10). The mixture was extracted with dichloromethane (4 x 40 mL). The combined organicextracts were dried over anhydrous Na2504, filtered and concentrated to dryness in vacuo.The residue was loaded onto an Isco solid load cartridge and purified by flashchromatography on 5i02 (0-6% MeOH/DCM) to give 5-chloro-7-methylthiazolo[5,4-bjpyridin-2-amine (0.33 g, 1.7 mmol, 59% yield) as a tan solid. MS (ESI) m/z: 199.9 [M+Hf ?H NMR (500 MI-Tz, DMSO-d6) oe 7.90 (s, 2H), 7.22 (s, 1H), 2.41 (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 129432-25-3, 2,6-Dichloro-4-methylpyridin-3-amine.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; CARPENTER, Joseph E.; BROEKEMA, Matthias; FENG, Jianxin; LIU, Chunjian C.; WANG, Wei; WANG, Ying; (244 pag.)WO2019/89670; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 54718-39-7, 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 54718-39-7, name is 2,5,6-Trichloronicotinic acid. This compound has unique chemical properties. The synthetic route is as follows.

1,1′-Carbonyldiimidazole (40 g, 247 mmol) was added in portions to 2,5,6-trichloronicotinic acid (50.7 g, 224 mmol, Combi-Blocks, San Diego, Calif., USA) in THF (400 mL), allowing gas evolution to cease between additions. The resulting mixture was stirred for 5 min and then was degassed with house vacuum and flushed with nitrogen (*2). The resulting mixture was heated to 50 C. for 60 min, then diluted with toluene (100 mL) and concentrated to half volume. The resulting mixture was cooled to 0 C. and ammonium hydroxide (60 mL, 437 mmol) was added slowly via syringe. The reaction was stirred for 10 min at room temperature, diluted with EtOAc (200 mL) and washed with water (3*100 mL). The organic layer was dried over anhydrous sodium sulfate and concentrated. The residue was suspended in 9:1 heptane/EtOAc (300 mL) and filtered. The filtered solids were collected and the remaining mother liquor was partially evaporated to half volume, cooled to 0 C., and filtered. The two crops of filtered solids were combined to provide 2,5,6-trichloronicotinamide (Intermediate P, 46.2 g, 92% yield).

According to the analysis of related databases, 54718-39-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Amgen Inc.; ALLEN, John Gordon; LANMAN, Brian Alan; CHEN, Jian; REED, Anthony B.; CEE, Victor J.; LIU, Longbin; LOPEZ, Patricia; WURZ, Ryan Paul; NGUYEN, Thomas T.; Booker, Shon; ALLEN, Jennifer Rebecca; CHU-MOYER, Margaret; AMEGADZIE, Albert; CHEN, Ning; GOODMAN, Clifford; LOW, Jonathan D.; MA, Vu Van; MINATTI, Ana Elena; NISHIMURA, Nobuko; PICKRELL, Alexander J.; WANG, Hui-Ling; SHIN, Youngsook; SIEGMUND, Aaron C.; YANG, Kevin C.; TAMAYO, Nuria A.; WALTON, Mary; XUE, Qiufen; US2019/374542; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 845306-04-9, 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.845306-04-9, name is 6-Chloro-N-methylpicolinamide, molecular formula is C7H7ClN2O, molecular weight is 170.5963, as common compound, the synthetic route is as follows.

A stirred solution of intermediate 2 (0.6g, 1.91 mmol) in dry 1,4-dioxane (10 mL), was added cesium carbonate (I.9g, 5.88 mmol) followed by 6-chloro-N-methylpicolinamide (0.25 g, 1.47 mmol, ABCR). Nitrogen was flushed into the solution for 20 mm and Pd(OAc)2 (0.016 g, 0.07 mmol) and 2-2?-bis (diphenylphosphino)-I-I?-binaphthyl (0.091g, 0.14 mmol) were added. The reaction mixture was stirred at 100 C for 12 h. The resulting reactionmixture was filtered through celite and evaporated under vacuum. Water (5 mL) was added and the mixture was extracted with EtOAc (5OmL). The organic layer was dried over anhydrous Na2SO4 and evaporated. The resulting crude product was purified by column chromatography ( brown solid). 1H NMR (400 MHz, DMSO-d6): 6 8.94-8.92 (m, 2H), 8.41 (d, J = 4.0 Hz, I H), 8.09 (d, J = 8.8 Hz, I H), 8.01 (5, 1 H), 7.94-7.94 (m, I H), 7.63 (t, J = 8.4 Hz, IH), 7.25-7.23 (m, IH), 6.94 (d, J = 8.4 Hz, IH), 3.79-3.77 (m, IH), 3.58-3.58 (m, 4H),2.77 (d, J = 4.80 Hz, 3H), 2.59-2.58 (m, 2H), 2.49-2.45 (m, 2H), 1.45 (d, J = 6.80 Hz, 3H). LCMS: (Method A) 377.2 (M +H), Rt. 2.14mm, 95.23% (Max). HPLC: (Method A) Rt. 2.07mm, 96.75% (Max).

Statistics shows that 845306-04-9 is playing an increasingly important role. we look forward to future research findings about 6-Chloro-N-methylpicolinamide.

Reference:
Patent; ASCENEURON S. A.; QUATTROPANI, Anna; KULKARNI, Santosh, S.; GIRI, Awadut, Gajendra; (280 pag.)WO2017/144633; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 122851-69-8, 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.122851-69-8, name is 3-Bromo-2-(chloromethyl)pyridine, molecular formula is C6H5BrClN, molecular weight is 206.47, as common compound, the synthetic route is as follows.

A solution of cis-4-(2,6-difluorophenyl)cyclohexanol (2.69 g) in THF (60 ml) wascooled to 0C, 60% sodium hydride (1.014 g) was added, and the mixture was stirredunder a calcium chloride tube dry atmosphere for 2 hr. To the reaction mixture wasadded 3-bromo-2-(chloromethyl)pyridine (3.40 g), and the mixture was stirred at roomtemperature for 30 min, and at 70C overnight. Water was added to the mixture atroom temperature, and the mixture was extracted with ethyl acetate. The organic layerwas washed with water and saturated brine, dried over anhydrous magnesium sulfate,and the solvent was evaporated under reduced pressure. The residue was purified bysilica gel chromatography (ethyl acetate/hexane) to give the title compound (3.96 g).MS, found: 382.0,384.0.

Statistics shows that 122851-69-8 is playing an increasingly important role. we look forward to future research findings about 3-Bromo-2-(chloromethyl)pyridine.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; FUJIMOTO Tatsuhiko; RIKIMARU Kentaro; FUKUDA Koichiro; SUGIMOTO Hiromichi; MATSUMOTO Takahiro; TOKUNAGA Norihito; HIROZANE Mariko; (166 pag.)WO2017/135306; (2017); 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. 100202-78-6, name is 2-(Bromomethyl)-6-fluoropyridine, molecular formula is C6H5BrFN, 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. Product Details of 100202-78-6

Dissolve (+/-)-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-1,2,3,4-tetrahydro-cyclopenta[b]indole-7-carbonitrile (6.88 g, 21.0 mmol) and 2-bromomethyl-6-fluoro-pyridine (3.99 g, 21.0 mmol) in DMF (80 mL). Add cesium carbonate (7.51 g, 23.1 mmol, 1.10 equivalents) and stir the reaction mixture at room temperature under nitrogen for 48 h. Dilute the reaction with ethyl acetate, wash with water (3×), dry over anhydrous sodium sulfate, filter, and concentrate to obtain a semi-solid (8.10 g). Purify the crude product on a 120 g silica gel column eluting with 0 to 100% ethyl acetate/hexanes to obtain 6.7 g of a tan/brown solid. Suspend the product in ether (100 mL) at room temperature overnight. Filter the solid, rinse with ether, and dry under high vacuum to obtain the title compound as a tan solid (5.70 g, 62%). LCMS 437.1 (M+1).

With the rapid development of chemical substances, we look forward to future research findings about 100202-78-6.

Reference:
Patent; Gavardinas, Konstantinos; Green, Jonathan Edward; Jadhav, Prabhakar Kondaji; Matthews, Donald Paul; US2010/69404; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem