Tag: M.W:200-300

Application of 168823-76-5, 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. 168823-76-5, name is 5-Bromo-2-(chloromethyl)pyridine. A new synthetic method of this compound is introduced below.

Example A50 Preparation of intermediate 50: (5-Bromo-pyridin-2-yl)-acetonitrile Potassium cyanide (0.489 g, 7.41 mmol) and potassium iodide (0.013 g, 0.079 mmol) were added to a stirred solution of 5-bromo-2-chloromethyl-pyridine (0.9 g, 3.70 mmol) (obtained by procedures similar to those described in, van den Heuvel, M. et al.; J. Org. Chem., 2004, 250) in a mixture of ethanol (6 ml) and water (2 ml). The mixture was stirred at 80 C. for 6 h., then diluted with dichloromethane and washed with a saturated solution of sodium hydrogen carbonate. The organic layer was separated, dried (Na2SO4), filtered and the solvents evaporated in vacuo. The crude product was purified by flash column chromatography (silica; dichloromethane). The desired fractions were collected and concentrated in vacuo to yield intermediate 50 (0.498 g, 68%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,168823-76-5, 5-Bromo-2-(chloromethyl)pyridine, and friends who are interested can also refer to it.

Reference:
Patent; Pastor-Fernandez, Joaquin; Bartolome-Nebreda, Jose Manuel; Macdonald, Gregor James; Conde-Ceide, Susana; Delgado-Gonzalez, Oscar; Vanhoof, Greta Constantia Peter; Van Gool, Michiel Luc Maria; Martin-Martin, Maria Luz; Alonso-de Diego, Sergio-Alvar; Swinney, Kelly Ann; Leys, Carina; Weerts, Johan Erwin Edmond; Wuyts, Stijn; US2011/269752; (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. 944401-56-3, name is 5-Bromo-4-(trifluoromethyl)pyridin-2-amine. A new synthetic method of this compound is introduced below., Quality Control of 5-Bromo-4-(trifluoromethyl)pyridin-2-amine

Example 9: Preparation of 5-(1 -ethoxyvinyl)-4-(trifluoromethyl)pyridin-2 -amine Bis(triphenylphosphine)palladium(ll)dichloride (0.74g, 1.0373 mmol) and 5-bromo-4- (trifluoromethyl)pyridin-2-amine ( 5 g, 20.75mmol) were stirred in dimethylformamide(10 mL) under nitrogen and the tributyl(1-ethoxyvinyl)stannane (7.5g, 20.75 mmol) was added. The mixture was heated to 80C for 2h, then to 100 degrees for a further 2h). The mixture was poured into saturated brine (250 mL) and was extracted with three portions of dichloromethane. The extracts were dried over anhydrous magnesium sulphate, and the solution was evaporated, giving an orange oil (4.0g, 83%) H NMR (CDCI3) 8.19(s, 1 H); 6.70(s, 1 H); 4.77(bs, 2H); 4.28(d,1 H); 4.23(d, 1 H); 3.86(q, 2H); 1.35(t,3H).

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, 944401-56-3, 5-Bromo-4-(trifluoromethyl)pyridin-2-amine.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; SYNGENTA LIMITED; CLOUGH, John Martin; BOEHMER, Jutta Elisabeth; PHADTE, Mangala; SONAWANE, Ravindra; LONGSTAFF, Adrian; MORRIS, James Alan; DESSON, Timothy Robert; HOTSON, Matthew Brian; RUSSELL, Sally; LING, Kenneth; BARNETT, Susan Patricia; BACON, David Philip; MOSELEY, Donn Warwick; MOUND, William Roderick; DOWLING, Alan John; WO2015/18432; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 552331-00-7 , The common heterocyclic compound, 552331-00-7, name is 4-Iodopyridin-2-amine, molecular formula is C5H5IN2, 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.

A mixture of (3S)-cyclopropyl-2-oxopyrrolidine-3-carbonitrile obtained in Step D of Example 1 (5.4 g), 4-iodopyridin-2-amine (7.2 g), N,N’-dimethylethane-1,2-diamine (1.5 mL), potassium carbonate (9.0 g) and copper(I) iodide (2.5 g) in 1,2-dimethoxyethane (60 mL) was stirred in a microwave reactor at 130 C. for 1 hr. The insoluble substance was removed through Celite, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (NH, ethyl acetate/methanol) to give the title compound (7.7 g). 1H NMR (400 MHz, DMSO-d6) delta0.46-0.55 (2H, m), 0.57-0.63 (1H, m), 0.64-0.72 (1H, m), 1.44-1.54 (1H, m), 2.27-2.37 (1H, m), 2.56-2.67 (1H, m), 3.81-3.91 (2H, m), 6.01 (2H, s), 6.74-6.84 (2H, m), 7.80-7.92 (1H, m). MS(ESI+): [M+H]+ 243.1.

The synthetic route of 552331-00-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; Saitoh, Morihisa; Yogo, Takatoshi; Kamei, Taku; Tokunaga, Norihito; Ohba, Yusuke; Yukawa, Takafumi; (191 pag.)US2016/159773; (2016); 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. 955370-07-7, name is 2-(6-Bromopyridin-2-yl)ethanol, molecular formula is C7H8BrNO, 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 955370-07-7

Step HThe title compound from Step G above (5 g, 24.75 mmol) was dissolved in N,N’-dimethylformamide (100 mL) and imidazole (4.84 g, 74.25 mmol) was added. After the addition of chlorotriisopropylsilane (7.92 mL, 37.1 mmol), the mixture was stirred at room temperature for 16 h. The reaction mixture was diluted with diethylether (300 mL) and washed with a 10% citric acid solution (3¡Á40 mL) and brine (100 mL). The organic phase was separated, dried over Na2SO4, filtered and the solvents were removed. The residue was purified by chromatography on silica using ethylacetate/n-heptane (5/95) to afford the title compound as a colorless liquid (7.36 g, 83%).1H-NMR (400 MHz, CDCl3): d=0.92-1.13 (m, 21H), 3.00 (t, 2H), 4.08 (q, 2H), 7.22 (d, 1H), 7.33 (d, 1H), 7.45 (t, 1H)

With the rapid development of chemical substances, we look forward to future research findings about 955370-07-7.

Reference:
Patent; AC Immune S.A.; US2011/92537; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 153034-94-7 , The common heterocyclic compound, 153034-94-7, name is 2-Fluoro-4-iodo-5-picoline, molecular formula is C6H5FIN, 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.

Preparation 18; 4-Benzo[¡ê]thiophen-7-yl-2-fluoro-5-methyl-pyridine; In a flask, combine 2-fluoro-4-iodo-5-methyl-pyridine (355 mg, 1.5 mmol), 2- benzo[¡ê]thiophen-7-yl-4,4,5,5-tetramethyl-[l,3,2]dioxaborolane (282 mg, 1.8 mmol), [l,r-bis(diphenylphosphino)ferrocene]dichloropalladium(II), complex with dichloromethane (1: 1) (61 mg, 0.07 mmol), 2-(di-tert-butylphosphino)biphenyl (13 mg, 0.04 mmol), sodium carbonate (2 M, 1.5 mL, 3 mmol) and THF (10 mL). Heat the mixture at 100 0C for 3 hours in an oil bath. Dilute the mixture with chloroform/isopropanol (3/1). Wash the solution with saturated aqueous sodium chloride. Dry over sodium sulfate. Concentrate in vacuo to a dark residue. Purify by column chromatography (20 % ethyl acetate in hexane) to afford the title compound (300 mg, 82 %) as yellow oil. MS (ES) m/z 244 [M+ 1]+.

The synthetic route of 153034-94-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ELI LILLY AND COMPANY; WO2008/76704; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 53636-56-9, Methyl 3-bromo-2-pyridinecarboxylate, 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, name: Methyl 3-bromo-2-pyridinecarboxylate, blongs to pyridine-derivatives compound. name: Methyl 3-bromo-2-pyridinecarboxylate

A mixture of N-cyclohexyl-N-isobutyl-2-nitro-4-(4,4,5,5-tetramethyl-1 ,3,2-dioxaboro lan-2- yl)aniline (1 .0 g, 2.5 mmol), methyl 3-bromopicolinate (594 mg, 2.75 mmol), tetrakis (144 mg, 0.125 mmol) and K2C03 (1 .04 g, 7.5 mmol) in DMF (5 mL) and H20 (1 mL) was stirred at 90C under N2 atmosphere overnight. The resulting mixture was partitioned between EtOAc and H20. The organic layer was washed with brine, dried over Na2S04, filtered and concentrated to give the crude product which was purified by flash chromatography (silica gel, 0-100% EtOAc in PE) to afford the title compound (900 mg, 91 % yield). LCMS (ESI) m/z calcd for C22H27N304: 397.20. Found: 396.12 (M-1)”.

The synthetic route of 53636-56-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; DE LA ROSA, Martha Alicia; KAZMIERSKI, Wieslaw Mieczyslaw; SAMANO, Vicente; (369 pag.)WO2018/116107; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1210419-26-3, 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.1210419-26-3, name is Methyl 6-bromo-5-fluoropicolinate, molecular formula is C7H5BrFNO2, molecular weight is 234.02, as common compound, the synthetic route is as follows.

In a sealed tube, a mixture of 2-[2,6-difluoro-4-(methylthio)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1.00 g, 3.49 mmol), methyl 6-bromo-5-fluoropyridine-2-carboxylate (1.23 g, 5.24 mmol) and DIPEA (1.83 mL, 10.5 mmol) in a mixed solvent of 1,4-dioxane (15 mL) and water (0.51 mL) was stirred and flushed with nitrogen bubbles for 5 min. before bis(tri-tert-butylphosphine)palladium (360 mg, 0.70 mmol) was added. The reaction mixture was heated at 120 C. for 30 min. After cooling, the reaction mixture was filtered, and the filter was washed with THF. The filtrate was concentrated and then purified by silica gel column chromatography using CombiFlash (0 to 20% EtOAc in hexanes) to give the sub-title compound as powder (442 mg, 40%). LCMS calc. for C14H11F3NO2S (M+H)+: m/z=314.1. Found: 314.2.

The chemical industry reduces the impact on the environment during synthesis 1210419-26-3, I believe this compound will play a more active role in future production and life.

Reference:
Patent; INCYTE CORPORATION; Xue, Chu-Biao; Li, Yun-Long; Geng, Hao; Pan, Jun; Wang, Anlai; Zhang, Ke; Yao, Wenqing; Zhang, Fenglei; Zhuo, Jincong; US2014/200227; (2014); 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. 100367-40-6, name is 2-Amino-5-bromo-4-methyl-3-nitropyridine. A new synthetic method of this compound is introduced below., Computed Properties of C6H6BrN3O2

To a solution of 5-bromo-4-methyl-3-nitropyridin-2-amine (28 g, 121 mmol) in water (900 ml) was added H2S04 (28 ml) followed by NaN02 (20.91 g, 303 mmol) in water (100 ml) drop wise at 0C. The reaction mixture was slowly warmed to room temperature for 2h, the reaction mixture was heated at 100C for 4h. The solid formed in reaction mixture was filtered and dried to afford title compound as a pale yellow solid (24.0 g, 85 %); 1H NMR (400 MHz, DMSO-de) delta 12.97 (s, 1H), 8.01 (s, 1H), 2.21 (s, 3H); LC/MS: 233 (M+l)+.

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, 100367-40-6, 2-Amino-5-bromo-4-methyl-3-nitropyridine.

Reference:
Patent; AURIGENE DISCOVERY TECHNOLOGIES LIMITED; BORUAH, Anima; CHITTY VENKATA, Srikanth; HOSAHALLI, Subramanya; PANIGRAHI, Sunil Kumar; WO2014/125408; (2014); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 67443-38-3, 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.67443-38-3, name is 5-Bromo-2-chloro-3-nitropyridine, molecular formula is C5H2BrClN2O2, molecular weight is 237.44, as common compound, the synthetic route is as follows.

Compound A (30.0 g), glycine-tert-butyl ester hydrochloride(23.3 g) and DMA (250 mL) was added triethylamine(38.4 mL) was added dropwise at 50 C. After completion of the dropwise addition,Followed by stirring at 50 C. for 2 hours. To the reaction mixture was added toluene (400 mL)And the mixture was washed with water, 1% hydrochloric acid and water in this order. After drying over sodium sulfate,A toluene solution of compound B was obtained.

Statistics shows that 67443-38-3 is playing an increasingly important role. we look forward to future research findings about 5-Bromo-2-chloro-3-nitropyridine.

Reference:
Patent; SUMITOMO DAINIPPON PHARMA COMPANY LIMITED; LEE, SHOUKOU; IWAMOTO, KOHEI; (57 pag.)JP2016/132649; (2016); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 72830-09-2 ,Some common heterocyclic compound, 72830-09-2, molecular formula is C8H11Cl2NO2, 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 1: Preparation of Pantoprazole sodium compound of formula-la:Added a solution of 2-chloromethyl-3,4-dimethoxypyridine hydrochloride (50 grams in 250ml of water) to a solution of 49.8 grams of 5-difluoromethoxy 2-mercaptobenzimidazole, 500 ml water and sodium hydroxide (22.5 grams of flakes in 27.5 ml of water), slowly at 25-35C. Stirred the reaction mixture for 3 hours. Extracted the reaction mixture thrice with methylene chloride. Separated the organic and aqueous layer. Washed the organic layer with water. Cooled the organic layer to -5 to 0C. Added 550 grams of 3.1% sodium hypochlorite solution having pH 8.75 and assay 3.2 to the above reaction mixture at -5 to 0C. Stirred the reaction mixture for 3 hours at -5 to 0C. Quenched the reaction mixture with 56 grams of ammonium sulphate at below 10C. Stirred the reaction mixture for 30 minutes. Separated the organic and aqueous phases. Extracted the aqueous phase twice with methylene chloride. Washed the organic layer with water. Dried the organic phase over sodium sulphate. Distilled the solvent completely under reduced pressure at below 45C. Added 37.5 ml of acetone to the above crude and distilled the solvent completely under reduced pressure at below 45C. Dissolved the residue in 375 ml of acetone at 25-35C. Heated the reaction mixture to reflux temperature. Stirred the reaction mixture for 30 minutes at reflux temperature. Cooled the reaction mixture to 18-23C. Added aqueous sodium hydroxide solution (8.5 grams in 10 ml of water) at 18-23C. Stirred the reaction mixture for 1 hour at 18-23C. Cooled the reaction mixture to 0-5C. Stirred the reaction mixture for 3 hours. Filtered the solid and washed with acetone followed by washed with methylene chloride. The obtained solid is purified in acetone to get pure compound.The amount of sulfone compound of formula-6 and compound of formula- 1 present in the obtained solid was measured using HPLC and the results are as follows. Yield: 65 grams Example-3: Preparation of pantoprazole sodium sesquihydrate compound of formula-la:Added a solution of 2-chloromethyl-3,4-dimethoxypyridine hydrochloride (50 grams in 250ml of water) to a solution of 49.8 grams of 5-difluoromethoxy-2- mercaptobenzimidazole, 500 ml of water and aqueous sodium hydroxide (22.5 grams of flakes in 27.5ml of water), slowly at 25-350C. Stirred the reaction mixture for 3 hours. Extracted the reaction mixture thrice with methylene chloride. Separated the organic and aqueous layer. Washed the organic layer with water. Added 550 grams of 3.1% sodium hypochlorite having pH 8.75 and assay 3.2 to the above reaction mixture at 25-300C for 2 hours. Stirred the reaction mixture for 10 hours at 25-3O0C. Quenched the reaction mixture with water at 25-300C. Stirred the reaction mixture for 30 minutes at 25-300C. Separated the organic and aqueous phases. Extracted the aqueous layer with methylene chloride. Washed the organic phase twice with aqueous sodium hydroxide solution. Separated the phases. Cooled the aqueous layer to 10-150C. Adjusted the pH of the reaction mixture to 9.3 with aqueous acetic acid. Added 250 ml of methylene chloride. Stirred the reaction mixture for 15 minutes. Separated the organic phase. Extracted the reaction mixture with methylene chloride. Washed the organic layer with water. Distilled the solvent completely from organic layer at below 45C under reduced pressure. Added 37.5 ml of acetone to the crude and distilled the solvent completely under reduced pressure at below 45C. Dissolved the residue in 375 ml of acetone at 25-35C. Heated the reaction mixture to reflux temperature. Stirred the reaction mixture for 30 minutes at reflux temperature. Cooled the reaction mixture to 18-23C. Added aqueous sodium hydroxide solution (8.5 grams in 10 ml of water) at 18-23C. Stirred the reaction mixture for 1 hour at 18-23C. Cooled the reaction mixture to 0-50C and 35 ml of methylene chloride was added. Stirred the reaction mixture for 3 hours. Filtered the solid and washed with methylene chloride. The above obtained compound can optionally purified as follows.Acetone (400 ml) was added to the above obtained wet compound and heated to reflux. The obtained solution was treated with carbon and cooled the filtrate to 0-5C. Stirred for 2 hours. Filtered the precipitated solid and washed with 30 ml of chilled acetone followed by washing with 50 ml of methylene chloride. Methylene chloride (250 ml) was added to the obtained wet compound at 25-35C. Stirred the reaction mixture for 90 minutes at 25-350C. Filtered the precipitated solid and washed with 25 ml of methylene chloride. Dried the compound at 40-500C for 10 hours.Yield: 70 grams W.C : 5.9 %HPLC : 99.93 %; 0.02 % (Sulfone Impurity) PSD : before micronization : D (v, 0.1) is 0.4 mum ; D (v, 0.5) is 8.73 mum; D (v, 0.9) is 27.7 mum andD(4,3) is 12.02 mum.PSD : after micronization 😀 (v,0.1) is 1.75 mum; D (v,Q.5) is 4.92 mum; D (v,0.9) is 13.10 mum andD(4,3) is 6.35 mum.Exam…

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. 72830-09-2, 2-Chloromethyl-3,4-dimethoxypyridinium chloride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MSN LABORATORIES LIMITED; WO2008/1392; (2008); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem