Pyridine-derivatives

Synthetic Route of 1370347-50-4, 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 1370347-50-4, name is (S)-1-(3,5-Dichloropyridin-4-yl)ethanol. This compound has unique chemical properties. The synthetic route is as follows.

Dissolve (S)-1-(3,5-dichloropyridin-4-yl)ethanol (5.02 g, 26.14 mmol) in dichloromethane (DCM, 100 mL) and cool the flask in an ice bath. Add triethylamine (TEA, 3.5 mL, 25.11 mmol) followed by the dropwise addition of methanesulfonyl chloride (2.2 mL, 28.42 mmol). Remove the ice bath and allow the reaction to warm to RT. After 4 hours, quench the reaction with water (100 mL) and separate layers. Extract the aqueous layer with DCM (50 mL) followed by 20% isopropyl alcohol (IPA)/chloroform (50 mL). Combine the organic extracts, dry over anhydrous sodium sulfate, filter and concentrate in vacuo. Yield: 7.15 g, (100%). MS (ES) m/z 270 [M+1]+.

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 1370347-50-4, (S)-1-(3,5-Dichloropyridin-4-yl)ethanol.

Reference:
Patent; ELI LILLY AND COMPANY; US2012/83511; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 944900-06-5, 2-Chloro-6-(trifluoromethyl)nicotinaldehyde, 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, Recommanded Product: 944900-06-5, blongs to pyridine-derivatives compound. Recommanded Product: 944900-06-5

To a stirred solution of 2-chloro-6-(trifluoromethyl)nicotinaldehyde (115 mg, 0.549 mmol) in THF (1 mL) was added dimethylamine (823 mul, 1.65 mmol). The reaction was heated to 500C and stirred for 3 hours. The reaction was loaded onto silica gel and eluted with 5% ethyl acetate/hexanes to 50% ethyl acetate/hexanes to yield the desired compound (50 mg, 0.229 mmol, 41.8 % yield).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,944900-06-5, 2-Chloro-6-(trifluoromethyl)nicotinaldehyde, and friends who are interested can also refer to it.

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

Application of 436799-33-6, 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. 436799-33-6, name is 3-Bromo-5-(trifluoromethyl)pyridine, molecular formula is C6H3BrF3N, 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.

Example 1.1.27: (5-(trifluoromethyl)pyridin-3-yl)methanamine; 3-bromo-5-(trifluoromethyl)pyridine (1.0 g, 4.42 mmol, 1 eq) was dissolved in 20 mL anhydrous DMF. The solution was degassed by bubbling through with Ar. Zn(CN)2 (0.312 g, 2.65 mmol, 0.6 eq) and Pd(PPh3)4 were added, and the resulting solution was heated to 80 0C with stirring overnight. The reaction was cooled to room temperature and diluted with Et2O. NH4OH (28%) was added with stirring and the layers were separated. The organic layer was washed with water (x3), brine (xl), and dried over Na2SO4. The inorganics were filtered off, and the reaction mixture was concentrated in vacuo. Purification via flash chromatography on silica gel yielded 0.310 g (1.95 mmol, 44% yield) of 5- (trifluoromethyl)nicotinonitrile.

According to the analysis of related databases, 436799-33-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; COMENTIS, INC.; PURDUE RESEARCH FOUNDATION; WO2009/42694; (2009); 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. 153747-97-8, name is tert-Butyl 4-(5-bromopyridin-2-yl)piperazine-1-carboxylate, molecular formula is C14H20BrN3O2, 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. Recommanded Product: 153747-97-8

To a stirred solution of tert-butyl 4-(5-bromopyridin-2-yl)piperazine-1-carboxylate (10 g, 29.21 mmol) in 1,4-dioxane (5OmL), 4N HCI solution in dioxane (100 mL, IOV) was added and the mixture was stirred 4 h at rt. The white precipitate formed was filtered and residuewas washed with diethyl ether (25 mL) to afford the title compound. Yield: 95.2% (9 g, off white solid). 1H NMR (400 MHz, DMSO-d6): 6 10.05 (br s, 2H), 8.21 (d, J = 2.4 Hz, IH), 7.82 (dd, J = 9.2, 2.4 Hz, IH), 6.99 (d, J = 9.2 Hz, IH), 3.80-3.77 (m, 4H), 3.33-3.13 (m, 4H). LCMS: (Method A) 243.9 (M +2H), Rt. 1.69 mm, 99.3 % (Max).

With the rapid development of chemical substances, we look forward to future research findings about 153747-97-8.

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 884495-38-9 ,Some common heterocyclic compound, 884495-38-9, molecular formula is C7H6ClNO, 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.

General procedure: To a solution of Intermediate 15B (0.50 g, 4.46 mmol) and 6bromo4methoxynicotinonitrile (0.95 g, 4.46 mmol) in dioxane (20 mL) was added K2CO3 (1.54 g, 11.15 mmol) and XANTPHOS (0.52 g, 0.89 mmol) and the resulting reaction mixture was degassed with nitrogen for 5 minutes. Pd2(dba)3(0.41 g, 0.45 mmol) was added and the resulting mixture was degassed again for 5 minutes then heated at 100 C for 16 h. The reaction mixture was cooled to ambient temperature, filtered through Celite and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography (Redisep24 g, 2 2.5 % MeOH in DCM), to obtain Intermediate 15C (0.40 g, 36.70%) as a pale yellow solid.1H NMR (400 MHz, DMSOd6) G ppm 2.65 (t, J = 6.78 Hz, 2 H), 3.61 (td, J = 6.78, 5.02 Hz, 2 H), 4.10 (s, 3 H), 4.62 4.76 (m, 1 H), 7.58 (s, 1 H), 7.81 (s, 1 H), 8.47 (s, 1 H), 8.73 (s, 1 H). LCMS (MethodI): retention time 0.83 min, [M+H] 245.3

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,884495-38-9, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; YADAV, Navnath Dnyanoba; BHIDE, Rajeev S.; BORA, Rajesh Onkardas; GUNAGA, Prashantha; PANDA, Manoranjan; PRIESTLEY, Eldon Scott; RICHTER, Jeremy; (444 pag.)WO2018/222795; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 52378-63-9, (3-Aminopyridin-2-yl)methanol, 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, 52378-63-9, blongs to pyridine-derivatives compound. HPLC of Formula: C6H8N2O

(i) A solution sodium nitrite (2.38 g) in water (10 ml) was added dropwise to a stirred mixture of 3-amino-2-hydroxymethylpyridine (4.8 g) in aqueous hydrochloric acid (48% 10 ml) and water (5 ml) at 0-5 C. This solution of the diazonium salt was added to a hot solution of cuprous chloride (2.5 g) in conc. hydrochloric acid and following cessation of nitrogen evolution the mixture was heated on the steam bath for 0.5 hours, diluted with water and saturated with hydrogen sulphide. Filtration, concentration to low bulk and extraction with chloroform yielded 3-chloro-2-hydroxymethylpyridine (3.7 g), m.p. 42-44 (from n-pentane).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,52378-63-9, its application will become more common.

Reference:
Patent; Smith Kline & French Laboratories Limited; US4025527; (1977); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 33252-28-7, 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. 33252-28-7, name is 6-Chloronicotinonitrile, molecular formula is C6H3ClN2, 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.

Example 29 6-Bromonicotinonitrile. 6-Chloronicotinonitrile (13.8 g, 100 mmol) was heated at 145 C. in phosphorus tribromide (150 mL) for 32 h. After cooling, the mixture was concentrated in vacuo. To the residue was added phosphorus tribromide (150 mL), and the mixture was heated at 145 C. for another 32 h. After cooling, the mixture was concentrated in vacuo, and an ice-water mixture (500 mL) was added. Sodium bicarbonate was added to neutralize the mixture, and the product was extracted with ethyl acetate (3*250 mL). The combined organic extracts were washed with brine and dried over magnesium sulfate. The solvent was removed in vacuo, and the residue was chromatographed (hexanes-ethyl acetate) to give 14.9 g (81 %) of 6-bromonicotinonitrile as a white solid: 1H NMR (400 MHz, CDCl3) delta 7.66 (d, J=11.0 Hz, 1H), 7.80 (dd, J=3.1, 11.0 Hz, 1H), 8.67 (d, J=3.1 Hz, 1H); MS (M+H)+ m/z=183.0, 185.0.

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 33252-28-7, 6-Chloronicotinonitrile.

Reference:
Patent; Xue, Chu-Biao; Metcalf, Brian W.; Han, Amy Qi; Robinson, Darius J.; Zheng, Changsheng; Wang, Anlai; Zhang, Yingxin; US2005/192302; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 63237-88-7, Pyrazolo[1,5-a]pyridine-2-carboxylic acid, 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: C8H6N2O2, blongs to pyridine-derivatives compound. HPLC of Formula: C8H6N2O2

General procedure: A solution of P(OMe)3 (1.5mmol) in DCM (10mL) was cooled with an ice bath, then I2 (1.5mmol) was added. After the solid iodine was completely dissolved, corresponding acid (1.2mmol) and Et3N (3.0mmol) were added in sequential order, and the solution was stirred for 15min in a cooling bath. Intermediate 5 (1.0mmol) was added and the mixture was stirred for 15min. After removing the cooling bath, the reaction mixture was stirred for 3.5hat room temperature, then diluted with saturated aqueous NaHCO3 and extracted with DCM (10mL) three times. The combined organic layer was sequentially washed with water and brine, dried with anhydrous Na2SO4, and concentrated in vacuo. The crude was purified by column chromatography with DCM/methanol (100:1 to 50:1, v/v) to give the product as a white solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,63237-88-7, Pyrazolo[1,5-a]pyridine-2-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Article; Bai, Renren; Shi, Qi; Liang, Zhongxing; Yoon, Younghyoun; Han, Yiran; Feng, Amber; Liu, Shuangping; Oum, Yoonhyeun; Yun, C. Chris; Shim, Hyunsuk; European Journal of Medicinal Chemistry; vol. 126; (2017); p. 464 – 475;,
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. 13466-35-8, name is 3-Chloro-2-hydroxypyridine, the common compound, a new synthetic route is introduced below. name: 3-Chloro-2-hydroxypyridine

Chlorination: 40 g of 3-chloro-2-hydroxypyridine and 100 g of dichloroethane,DMF0.3g,Phosphorus oxychloride 56g was added to the reaction flask and refluxed.In the control,After the reaction is over,Distilled ethylene dichloride,Slowly add cold water to the reaction solution.After fully hydrolyzing, adjust the pH to 4-5 and steam it.Get 2,3-dichloropyridine,Dry at room temperature and dry at 43gThe purity is 99.1%.

The synthetic route of 13466-35-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Suzhou Kaiyuan People’s Welfare Technology Co., Ltd.; Zhao Fei; Song Liang; Chen Wei; Wei Haihao; Zeng Miao; Xu Jianfeng; (8 pag.)CN107935921; (2018); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 69045-78-9 ,Some common heterocyclic compound, 69045-78-9, molecular formula is C6H3Cl4N, 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.

The obtained 2-chloro-5-trichloromethylpyridine 46.2 g,After adding the catalyst, the temperature is raised to 150-160C.Slowly dry the chlorine gas for heavy chlorination.After 6 hours of reaction, dilute the reaction solution with benzene, wash with water and dry the organic phase.After evaporating the benzene under reduced pressure,After distillation, 50.3 g of oily product was obtained.That is the intermediate 2,3-dichloro-5-trichloromethylpyridine,The yield was 90% and the content was 95%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,69045-78-9, its application will become more common.

Reference:
Patent; Shandong Eastern Countries Nong Pharmaceutical Ji Industrial Co., Ltd.; Yu Lexiang; Li Yuan; Liu Weihua; Sun Meixin; Sun Fujiang; (7 pag.)CN106748985; (2017); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem