Tag: M.W:100-200

Reference of 709652-82-4 , The common heterocyclic compound, 709652-82-4, name is 2-Amino-5-bromonicotinonitrile, molecular formula is C6H4BrN3, 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.

Example 126 Step 1: (6-amino-5-cyanopyridin-3-yl)boronic acid and 2-amino-5-(4,4,5,5-tetramethyl-l,3,2- dioxaborolan-2-yl)nicotinonitrile To a stirred solution of 2-amino-5-bromonicotinonitrile (100 mg, 0.51 mmol) and 1,2- dimethoxyethane (4 mL) in a microwave vial equipped with a stirbar was added bis(pinacolato diborane) (175 mg, 0.66 mmol), potassium acetate (149 mg, 1.52 mmol) and 1,1′- bis(diphenylphosphino)ferrocene-palladium(II)dichloride (21 mg, 0.025 mmol). The mixture was purged with nitrogen gas for 5 min and the reaction mixture was stirred at 90 C for 3 h. The reaction mixture was filtered through a celite bed and washed with dichloromethane (10 mL). The filtrate was concentrated to dryness in vacuo affording a crude mixture of (6-amino-5-cyanopyridin-3-yl)boronic acid and 2-amino-5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)nicotinonitrile used for the next step without any further purification. Step 2: 2-amino-5-(4-cyclopropyl-6,6-dimethyl-8,9-dihydro-6H-[l,4]oxazino[4,3-e]purin-2- yl)nicotinonitrile 2-chloro-4-cyclopropyl-6,6-dimethyl-8,9-dihydro-6H-[l,4]oxazino[4,3-e]purine (50 mg, 0.18 mmol) and a crude mixture of (6-amino-5-cyanopyridin-3-yl)boronic acid and 2-amino-5-(4,4,5,5- tetramethyl-l,3,2-dioxaborolan-2-yl)nicotinonitrile (120 mg) was dissolved in acetonitrile (2.5 mL) and degassed water (0.5 mL) in a microwave vial equipped with a stirbar. To the solution was added bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) (12.7 mg, 0.018 mmol), potassium acetate (25 mg, 0.25 mmol) and sodium carbonate (27 mg, 0.25 mmol) and the mixture was microwaved at 140 C for 40 min. The reaction mixture was filtered through a celite bed and washed with dichloromethane (10 mL). The filtrate was concentrated to dryness in vacuo. The resulting residue was purified by RP-HPLC affording 2-amino-5-(4-cyclopropyl-6,6-dimethyl-8,9-dihydro-6H- [l,4]oxazino[4,3-e]purin-2-yl)nicotinonitrile (4.1 mg, 6%, two steps): LCMS RT = 5.07 min, m/z = 362.2 [M + H]+.

The synthetic route of 709652-82-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; ESTRADA, Anthony; HUESTIS, Malcolm; KELLAR, Terry; PATEL, Snahel; SHORE, Daniel; SIU, Michael; (260 pag.)WO2016/142310; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 147740-04-3, Adding some certain compound to certain chemical reactions, such as: 147740-04-3, name is Ethyl 1H-pyrrolo[3,4-c]pyridine-2(3H)-carboxylate,molecular formula is C10H12N2O2, 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 147740-04-3.

d) 2,3-Dihydro-1H-pyrrolo[3,4-c]pyridine dihydrochloride 10.4 g (51 mmol) of ethyl 2,3-dihydro-1H-pyrrolo-[3,4-c]pyridine-2-carboxylate are refluxed for 15 hours together with 100 ml of concentrated hydrochloric acid. The batch is evaporated, and the crystalline residue is stirred with acetone. The product is filtered off with suction and dried in the air. Yield: 9.8 g (100percent of theory)

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. 147740-04-3, Ethyl 1H-pyrrolo[3,4-c]pyridine-2(3H)-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Bayer Aktiengesellschaft; US5312823; (1994); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 4214-74-8 , The common heterocyclic compound, 4214-74-8, name is 3,5-Dichloropyridin-2-amine, molecular formula is C5H4Cl2N2, 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-bromo-3,5-dichloropyridine [0239] To a solution of 3,5-dichloropyridin-2-amine (1.0 g, 6.2 mmol) in 40% aqueous HBr (8 mL) was added dropwise bromine (2.8 g, 17 mmol) at -20C. The orange suspension was stirred for 2hrs at -20C, and followed by addition of the aqueous NaN02 (1.1 g, 17 mmol) at -20C. The mixture thus obtained was stirred for an additional 2 hours at ambient temperature. The brown mixture was basified with 30% aqueous NaOH to pH ~12 at 0C. The pale yellow mixture was extracted with ether. The combined organic phases were washed with brine, dried over Na2S04 and concentrated to afford the title compound as yellow solid (730 mg, 52%). 1H NMR (400 MHz, CDC13) delta 8.27 (d, J J= 2.3 Hz, 1H).

The synthetic route of 4214-74-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; RUGEN HOLDINGS (CAYMAN) LIMITED; SHAPIRO, Gideon; (119 pag.)WO2015/187845; (2015); 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.178421-21-1, name is Ethyl 6-chloro-5-methylpicolinate, molecular formula is C9H10ClNO2, molecular weight is 199.63, as common compound, the synthetic route is as follows.name: Ethyl 6-chloro-5-methylpicolinate

l-[(2,2-difluorocyclopropyl)methyl]-3-methyl-5-(4,4,5,5-tetramethyl-1,3 ,2- dioxaborolan-2-yl)-1,3 -dihydro-2,1,3-benzothiadiazole 2,2-dioxide (12-1) (100 mg, 0.25 mmol, 1 eq), ethyl 6-chloro-5-methylpyridine-2-carboxylate (26-4) (75 mg, 0.38 mmol, 1.5 eq), tripotassium phosphate (106 mg, 0.50 mmol, 2.0 eq), S-Phos (10 mg, 0.025 mmol, 0.1 eq), and palladium(II) acetate (2.8 mg, 0.012 mmol, 0.05 eq) were combined in THF (1 mL) and water (0.2 mL). The resulting mixture was heated at 75 C for 14 hours. The reaction mixture was allowed to cool to room temperature. The mixture was then diluted with EtOAc (10 mL), washed with water (1 mL) and brine (1 mL), dried over MgS04, filtered and concentrated. The crude residue was purified by flash chromatography (12 g Si02, 0-80% EtOAc in hexanes) to afford ethyl 6- { 1 -[(2,2-difluorocyclopropyl)methyl]-3-methyl-2,2-dioxido- 1 ,3-dihydro-2, 1 ,3- benzothiadiazol-5-yl}-5-methylpyridine-2-carboxylate (26-5). HRMS m/z (M+H) 438.1291 found, 438.1294 required.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,178421-21-1, Ethyl 6-chloro-5-methylpicolinate, and friends who are interested can also refer to it.

Reference:
Patent; MERCK SHARP & DOHME CORP.; LAYTON, Mark, E.; KELLY, Michael, J.; HARTINGH, Timothy, J.; WO2011/109277; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 52378-63-9, name is (3-Aminopyridin-2-yl)methanol. A new synthetic method of this compound is introduced below., Formula: C6H8N2O

i. A solution sodium nitrite (2.28 g) in water (10 ml) was added dropwise to a stirred mixture of 3-amino-2-hydroxymethylpyridine (4.8 g) in aqueous hydrobromic 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 bromide (2.5 g) in 60% hydromic 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-bromo-2-hydroxymethylpyridine (4.8 g).

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, 52378-63-9, (3-Aminopyridin-2-yl)methanol.

Reference:
Patent; Smith Kline & French Laboratories Limited; US4000302; (1976); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 127915-50-8, 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.127915-50-8, name is 4-Amino-6-methylnicotinic acid, molecular formula is C7H8N2O2, molecular weight is 152.15, as common compound, the synthetic route is as follows.

The cake is washed with ether and dried in vacuo. In a similar manner, starting with 4-amino-6-methylnicotinic acid, the corresponding 4-amino-5-bromo-6-methylnicotinic acid is prepared.

The chemical industry reduces the impact on the environment during synthesis 127915-50-8, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Pfizer Inc.; US3950160; (1976); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1060805-95-9, 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. 1060805-95-9, name is 4-Chloro-6-methylnicotinic acid, molecular formula is C7H6ClNO2, 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.

Step 2: A mixture of 4-chloro-6-methyl-3-pyridinecarboxylic acid (10 g, 58.4mmol) and KMnO4 (27.7 g, 175.4 mmol) in H2O was reflux with stirring for 24 h. The mixture was cooled to temperature and filtrated. EtOH was added to the filtrate and filtrated again. The filtrate was concentrated by vacuo to give the crude product 17 g which was used directly to the next reaction without further purification.

According to the analysis of related databases, 1060805-95-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXOSMITHKLINE LLC; WANG, Yonghui; YU, Hongyi; WO2010/59552; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 920966-03-6, 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.920966-03-6, name is 4-Chloro-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid, molecular formula is C8H5ClN2O2, molecular weight is 196.59, as common compound, the synthetic route is as follows.

Preparation 32To a solution of 4-chloro-lH-pyrrolo[2, 3-b]pyridine-5- carboxylic acid (840mg) inN,N-dimethylformamide (8.4mL) were added 1-hydroxybenzotriazole (808 mg) and 1- (3-dimethylaminopropyl) – 3-ethylcarbodiimide (929 mg) . The mixture was stirred at 600C for 30 minutes. The solution was cooled to ambient temperature and added EPO 28% ammonium hydroxide aqueous solution (1.2 ?iL) . The mixture was stirred at ambient temperature for 1 hour. To the solution were added water and chloroform and the mixture was extracted with chloroform.The extract was dried over MgSO4, filtrated and evaporated. The residue was purified by column chromatography on silica gel with chloroform and methanol (100:0 to 90:10) to give 4-chloro- lH-pyrrolo [2, 3-b]pyridine-5-carboxamide (90 mg) as a pale yellow powder.1H-NMR (DMSO-d6) delta : 6.55-6.57 (lH,m) , 7.63-7.66 (lH,m) , 7.90 (2H,br) ,8.2 9(lH,s) ,12.16(lH,brs) .MS (ESI) :m/z 218(M+Na)+.

Statistics shows that 920966-03-6 is playing an increasingly important role. we look forward to future research findings about 4-Chloro-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid.

Reference:
Patent; ASTELLAS PHARMA INC.; WO2007/7919; (2007); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 73406-50-5, Ethyl 3-hydroxypicolinate, 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, Computed Properties of C8H9NO3, blongs to pyridine-derivatives compound. Computed Properties of C8H9NO3

EXAMPLE 2 Preparation of ethyl 3-(4,6-dimethoxypyrimidin-2-yl)oxy picolinate (Compound No. 2) To 0.5 g of 60% sodium hydride, 50 ml of hexane was added, and subjected to decantation. Then, the mixture was suspended in 30 ml of dimethylformamide. To the dimethylformamide suspension, 1.9 g of ethyl 3-hydroxypicolinate was gradually added, and the 2.0 g of 2-chloro-4,6-dimethoxypyrimidine was added. The mixture was heated and stirred at a reaction temperature of from 130 to 140 C. for 4 hours. After cooling, the reaction solution was poured into water, and extracted with ethyl acetate. The extract was washed with water and dried over magnesium sulfate. Ethyl acetate was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (hexane-ethyl acetate) to obtain 1.4 g of ethyl 3-(4,6-dimethoxypyrimidin-2-yl)oxy picolinate. (Yield: 40%, pale yellow liquid, refractive index nD20 =1.5389)

The synthetic route of 73406-50-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Kumiai Chemical Industry Co., Ltd.; Ihara Chemical Industry Co., Ltd.; US4832729; (1989); A;,
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. 72093-04-0, name is 3-Chloro-4-methylpyridine, molecular formula is C6H6ClN, 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. Application In Synthesis of 3-Chloro-4-methylpyridine

To a solution of lithium diisopropylamide (3OmL, 2M in THF) at -70C is added under argon a solutionof 3-chloro-4-methylpyridine (6.3 8g, 1 eq, SOmmol) in 25mL THF. The mixture is stirred for 5mm at -70C and then allowed to reach -30C. Thereafter the mixture is cooled down to -70C and a solution of 2-chloro- 1 -(1 -chlorocyclopropyl)ethanone (9.1 8g, 1 .2eq, 6Ommol) in 25mL THF is added. Then the mixture is allowed to reach ambient temperature and stirred for lh. Thereafter the mixture is cooled to 0C and saturated aqueous ammonium chloride solution is added. After extraction with ethyl acetate and evaporation of the solvent the crude material is purified via column chromatography over silica gel (eluent cyclohexane / ethyl acetate gradient). After evaporation of the solvent 1 Og (73%) of 3 -chloro-4- { [2-( 1-chlorocyclopropyl)oxiran-2-yl]methyl}pyridine are obtained as colourless oil.

With the rapid development of chemical substances, we look forward to future research findings about 72093-04-0.

Reference:
Patent; BAYER CROPSCIENCE AG; HOFFMANN, Sebastian; SUDAU, Alexander; DAHMEN, Peter; WACHENDORFF-NEUMANN, Ulrike; BERNIER, David; LACHAISE, Helene; BRUNET, Stephane; VIDAL, Jacky; GENIX, Pierre; COQUERON, Pierre-Yves; GEIST, Julie; VORS, Jean-Pierre; KENNEL, Philippe; MILLER, Ricarda; WO2014/167008; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem