Day: September 3, 2021

Synthetic Route of 65977-55-1, 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 65977-55-1, name is 5-Chlorothieno[3,2-b]pyridine. This compound has unique chemical properties. The synthetic route is as follows.

(A) A mixture of 1019 5-chlorothieno[3,2-b]pyridine (1.8 g, 10.6 mmol), PdCl2(dppf).CH2Cl2 (866 mg, 1.06 mmol) and 57 Et3N (3 mL) in 21 MeOH (15 mL) was stirred overnight at 110 C. under an atmosphere of CO (g) (60 atm). After cooling to rt, the reaction was quenched by the addition of satd. aq NH4Cl (50 mL) and the resulting solution was extracted with EtOAc (3×50 mL). The combined organic extracts were dried (Na2SO4), filtered and concentrated under reduced pressure. The resultant residue was purified by silica gel chromatography (0-25% EtOAc/petroleum ether) to afford 1020 methyl thieno[3,2-b]pyridine-5-carboxylate (1.7 g, 82%), as a yellow solid. LC/MS: mass calcd. for C9H7NO2S: 193.02, found: 193.8 [M+H]+.

According to the analysis of related databases, 65977-55-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Janssen Pharmaceutica NV; Meegalla, Sanath; Player, Mark R.; Huang, Hui; Winters, Michael P.; (98 pag.)US2017/291908; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 69627-02-7, 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. 69627-02-7, name is Thieno[3,2-b]pyridin-7(4H)-one, molecular formula is C7H5NOS, 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 thieno[3,2-b]pyridin-7-ol (1,2.55g, 16.87 mmol) in acetic acid(50mL) was added bromine(1.7 mL, 32.72 mmol). The mixture was heated at 110C for Ih,cooled and the resultant precipitate was separated by filtration, to afford the title compound270 (4.47g, crude) as a dark brown powder, which was used in next step without furtherpurification. M/S (m/z): 231.9(M+H) (found).

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 69627-02-7, Thieno[3,2-b]pyridin-7(4H)-one.

Reference:
Patent; METHYLGENE, INC.; WO2006/10264; (2006); 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. 189281-48-9, name is 2,4-Dichloro-5-fluoropyridine, the common compound, a new synthetic route is introduced below. Recommanded Product: 2,4-Dichloro-5-fluoropyridine

Example 10d6-Chloro-2-(4-chloro-phenyl)-3-fluoro-pyridine A solution of 2.2 g 2,4-chloro-5-fluoropyridine, 2.28 g 4-chlorophenylboronic acid and 0.6 g tetrakistriphenylphosphine palladium in 30 ml tetrahydrofuran was added 30 ml of a 10% a solution of potassium carbonate in water and the mixture was stirred at ambient temperature for 18 h. The reaction mixture was diluted with ethyl acetate and water. The phases were separated and the organic phase was washed water, 10% aqueous citric acid, 10% aqueous sodium bicarbonate and brine, dried over sodium sulfate and evaporated. The residue was purified by chromatography on silica gel with a gradient of heptane_dichloromethane=9:1 to 1:1 (only startspot was removed) The product fractions were collected and evaporated. The residue was subjected to Kugelrohr distillation at 0.03 mbar and 110 C. to yield 1.72 g of the title compound as colorless oil which solidified into white crystals. MS (EI) (M+H): 241 and 243:

The synthetic route of 189281-48-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hebeisen, Paul; Roever, Stephan; US2012/157476; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 142266-62-4, Adding some certain compound to certain chemical reactions, such as: 142266-62-4, name is 2,5,6-Trichloronicotinamide,molecular formula is C6H3Cl3N2O, 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 142266-62-4.

[0546] Into a 100-mL 3 -necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen were placed a solution of 2,5,6-trichloronicotinamide (4.00 g, 17.9 mmol, 1.00 equiv) in DMF (30 mL) and 5-hydroxypentan-2-one (2.00 g, 19.6 mmol, 1.10 equiv). This was followed by the addition of sodium hydride (470 mg, 19.58 mmol, 1.10 equiv) in portions at 0 C. The resulting solution was stirred overnight at room temperature. The reaction was then quenched by the addition of 40 mL of water. The solid was collected by filtration and dried in an oven under reduced pressure. This resulted in 2.31 g (40%>) of 5,6-dichloro-2-(4- oxopentyloxy Nicotinamide as a yellow solid.

According to the analysis of related databases, 142266-62-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ANACOR PHARMACEUTICALS, INC; JARNAGIN, Kurt; AKAMA, Tsutomu; WO2011/94450; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 5223-06-3 ,Some common heterocyclic compound, 5223-06-3, molecular formula is C9H13NO, 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 100 g (0.655 mol) [2- (5-ETHYL-PYRIDIN-2-YL)-ETHANOL] in 500 mL acetic acid was added 118 g (1.049 mol) 30% hydrogen peroxide at 25-30 [C.] Reaction mixture was refluxed at 100 [C] [(TLC)] for 14 hr. After completion of the reaction acetic acid was removed under vacuum, and the residual mass was poured in excess water and made alkaline by 10% [NA2C03] solution. Product was extracted with ethyl acetate and after concentrating ethyl acetate [IN VACUO, 89. 58 G (81%)] crystalline product was obtained. The product obtained was characterized by Mass, [13C] NMR, [AND’H] NMR, which are as given below. Mass spectrum (m/z) : 168. 1 (M + [H) +] [3C-NMR] [(CDC13)] [: 6] 170.7, 148.2, 138.7, 135.9, 125. 8,62. 0,34. 2,25. 5, 14.4 ‘H-NMR [(CDC13)] : [S] 7.07-8. 14 (3H, m), 5.7 [(1H,] broad s), 3.9 (2H, t), 3.2 (2H, t), 2.6 (2H, q), 1.2 (3 H, t)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,5223-06-3, its application will become more common.

Reference:
Patent; CADILA HEALTHCARE LIMITED; WO2004/7490; (2004); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 52313-50-5, Adding some certain compound to certain chemical reactions, such as: 52313-50-5, name is Picolinimidamide,molecular formula is C6H7N3, 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 52313-50-5.

A solution of 1-(2,4-difluorophenyl)piperidin-4-one (0.24 g, 1.14 mmol) and DMFDMA (0.5 mL) in acetonitrile (5 ml) was heated with stuffing at 90 C for 2 hrs. The mixture was concentrated in vacuo and the residue was dissolved in EtOH (lOmL). To the solution was addedpyridine-2-carboxamidine (91 mg, 0.75 mmol) and potassium carbonate (210 mg, L50 mmol) successively. After being heated at 90 C overnight, the resulting mixture was cooled to rt, diluted with water (20 mL) and extracted with EA (20 mL) for three times. The organic layers were washed with brine, dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by prep-HPLC to give 6-(2,4-difluorophenyl)-2-(2-pyridyl)-7,8-dihydro-5H-pyrido[4,3-d]pyrimidine (6 mg). ?H NMR (400MHz, DMSO-d6): oe 8.77 (s, 1H), 8.74 (d, 1H),8.36 (d, 1H), 7.97 (dt, 1H), 7.52 (ddd, 1H), 7.34 – 7.16 (m, 2H), 7.14 – 6.97 (m, 1H), 4.33 (s, 2H),3.48 (t, 2H), 3.10 (t, 2H). MS obsd. (ESIj [(M+H)]: 325.

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. 52313-50-5, Picolinimidamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; CHENG, Zhanling; WANG, Min; YANG, Song; (208 pag.)WO2016/107832; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 73290-22-9, 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.73290-22-9, name is 2-Bromo-5-iodopyridine, molecular formula is C5H3BrIN, molecular weight is 283.89, as common compound, the synthetic route is as follows.

To a solution of 2-bromo-5-iodopyridine (15 g, 52.8 mmol) in dry THF (300 mL) at -78C was added n-BuLi (2.5 M, 21 mL), and stirred at -78 C for 1 hrs, followed by addition of tert-butyl 3-oxopiperidine-1-carboxylate (10.5 g, 52.8 mmol) in THF. The reaction mixture was stirred at -78 C–6O C for 2 hrs, quenched by NH4C1/H20 and extracted by EA. The organic was dried to give a residue, which was purified by flash chromatography to afford the titlecompound (8.4 g, 45%). MS (ES+) C15HnBrN2O3 requires: 356, found: 357 [M+H].

The chemical industry reduces the impact on the environment during synthesis 73290-22-9, I believe this compound will play a more active role in future production and life.

Reference:
Patent; BLUEPRINT MEDICINES CORPORATION; BROOIJMANS, Natasja; BRUBAKER, Jason, D.; FLEMING, Paul, E.; HODOUS, Brian, L.; KIM, Joseph, L.; WAETZIG, Josh; WILLIAMS, Brett; WILSON, Douglas; WILSON, Kevin, J.; (347 pag.)WO2017/181117; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 717843-48-6, 3-Bromo-6-methylpicolinonitrile, 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: C7H5BrN2, blongs to pyridine-derivatives compound. HPLC of Formula: C7H5BrN2

(3) the 2 – bromo -6 – methyl -2 – cyano pyridine (25g, 127mmol) dissolved in the 1L in concentrated hydrochloric acid (HCl), mixture in 110 C stirring reaction under the condition of 2 days; removing the solvent to obtain crude product; the obtained crude product is dissolved in water, and addingNaHCO3, then filtered; the filtrate is ethyl acetate extraction, Na2SO4drying and vacuum concentrated to get the crude product 3 – bromo -6 – methyl -2 – picolinic acid; two product adds up the yield of 69.3%, about 19g.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,717843-48-6, 3-Bromo-6-methylpicolinonitrile, and friends who are interested can also refer to it.

Reference:
Patent; Suzhou Jianxiong Vocational and Technical College; Gu, Zhun; Wang, Yang; Jin, Chen; (7 pag.)CN106045902; (2016); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 58539-77-8, 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. 58539-77-8, name is 3-(Chloromethyl)-2-methylpyridine hydrochloride. A new synthetic method of this compound is introduced below.

A mixture of the compound of Example 42 (0.20 g, 0.57 [MMOL),] cesium carbonate (2.0 g, 5.7 [MMOL)] and 3-chloromethyl-2-methyl-pyridine hydrochloride (0.16 g, 0.91 [MMOL)] in a 2: 1 THF/DMF mixture was heated at [80C] for 15 hours. The cooled mixture was filtered and concentrated, and then water (30 mL) was added and the mixture extracted with ethyl acetate (3 x 30 mL). The combined organic layers were washed with brine, dried [(MGS04),] filtered and concentrated to a foam (0.31 [G).] The residue was purified by flash chromatography using a 30% to 70% ethyl acetate/hexanes eluant to afford 122 mg (47%) of the title compound as an oil. Mass spectrum: (m/e) 458 (M++1, +ion).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,58539-77-8, its application will become more common.

Reference:
Patent; PFIZER PRODUCTS INC.; WO2004/5229; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 14482-51-0, 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.14482-51-0, name is 2-Bromo-3,5-dichloropyridine, molecular formula is C5H2BrCl2N, molecular weight is 226.89, as common compound, the synthetic route is as follows.

NMP (7 mL) was added to a round bottom, placed under nitrogen and cooled to 00C. NaH (1.16 g, 29.1 mmol) was added portionwise followed by the addition of methyl cyanoacetate (1.31 ml, 14.5 mmol) (in 3 mL of NMP) dropwise. After stirring for 30 minutes at 00C, 2- bromo-3,5-dichloropyridine (3.0 g, 13.2 mmol) was added and the reaction was heated to 1300C for 5 hours. The reaction was allowed to cool, poured into ice and extracted twice with ethyl acetate. The ethyl acetate was combined, dried over MgSO4, filtered and concentrated. The amorphous material was crystallized from methanol to afford the desired compound (700 mg, 2.86 mmol, 21.6 % yield) as light brown needles.

Statistics shows that 14482-51-0 is playing an increasingly important role. we look forward to future research findings about 2-Bromo-3,5-dichloropyridine.

Reference:
Patent; ARRAY BIOPHARMA INC.; COOK, Adam; HUNT, Kevin, W.; DELISLE, Robert Kirk; ROMOFF, Todd; CLARK, Christopher, T.; KIM, Ganghyeok; CORRETTE, Christopher, P.; DOHERTY, George, A.; BURGESS, Laurence, E.; WO2010/75200; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem