Day: April 18, 2022

Application of 117846-58-9, 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. 117846-58-9, name is 2,6-Dibromo-3,5-dimethylpyridine, molecular formula is C7H7Br2N, 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 stirred solution of 2 (3.15 g, 11.87 mmol) in anhydrous THF (50 mL) was added dropwise a 2.5 M solution of n-BuLi in hexane (5.12 mL, 12.80 mmol) at 195 K. The reaction was stirred for 30 min at thistemperature, a solution of (2,5-Dimethyl-3-thienyl)perfluorocyclopentene (3.97 g,13.06 mmol) in THF (5 mL) was added. The reaction solution was stirred for 1 hat this temperature. The reaction was allowed to warm to room temperature, andquenched with water (15 mL). The product was extracted with diethyl ether. Theorganic layers were combined, dried over anhydrous Na2SO4,filtered, and concentrated in vacuo. Column chromatography on Al2O3(hexane) afforded diarylethene 4 (1.62 g, 29%) as a colorless crystal, mp 96-97 C; 1H NMR(400 MHz, CDCl3): delta 7.29(s, 1H, pyridine-H), 6.64 (s, 1H, thiophene-H), 2.38 (s, 3H, -CH3), 2.37(s, 3H, -CH3), 1.93 (s, 3H, -CH3), 1.84 (s, 3H, -CH3);13C NMR (100 MHz,CDCl3) delta 145.20, 141.66, 141.00,140.54, 137.87, 135.98, 132.68, 124.51, 123.61, 21.72, 17.43, 15.04, 14.26; IR(KBr, nu, cm-1): 3128, 1637,1587, 1400, 1274, 1126, 1188, 1060, 1004, 894, 826, 734, 707; LRMS, ESI+m/z 470.1 (MH+, C18H14BrF6NS requires 469.0); Anal. Calcd for C18H14BrF6NS: Calcd C, 45.97; H, 3.00; N, 2.98. Found C, 45.91; H, 3.02; N, 2.96

According to the analysis of related databases, 117846-58-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Zheng, Chunhong; Liu, Gang; Pu, Shouzhi; Tetrahedron Letters; vol. 54; 43; (2013); p. 5791 – 5794;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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 856013-04-2, name is 6-Bromopyridine-2-sulfonamide. This compound has unique chemical properties. The synthetic route is as follows. category: pyridine-derivatives

c) 6-(8-Oxo-5,6,7,8-tetrahydro-naphthalen-2-yl)-pyridine-2-sulfonamide6-Bromo-pyridine-2-sulfonamide (65mg, 0.27 mmol), 7-(4,4,5,5-Tetramethyl- [l,3,2]dioxaborolan-2-yl)-3,4-dihydro-2H-naphthalen-l-one (97mg, 0.36 mmol), tetrabutylammonium bromide (TBAB) (lOmg, 0.04 mmol) and Pd(PPh3)2Cl2 (13mg, 0.02 mmol) in dioxane:water (1.2 mL/0.6 mL) were heated at 1000C in a microwave reactor for 1 hour. After this time, water was added and the aqueous phase was extracted three times with ethyl acetate. The combined organic phases were washed with water and brine and dried over Na2SO4. Concentration afforded a brown solid which was triturated with Et2O. An off-white solid was obtained. Analysis (NMR) showed presence of impurities but the compound was on-reacted without further purification. NMR 1H (d6-DMSO, ppm): 8.6 (d, J = 2.1 Hz, IH), 8.36 (dd, J = 8.1 and 2.1 Hz, IH), 8.20 (dd, J = 9.03 and 1 Hz, IH), 8.11 (t, J = 7.6 Hz, IH), 7.85 (dd, J = 7.6 and 1 Hz, IH), 7.53-7.50 (m, 3H), 3.01-2.98 (m, 2H), 2.66-2.62 (m, 2H), 2.10-2.04 (m, 2H).

With the rapid development of chemical substances, we look forward to future research findings about 856013-04-2.

Reference:
Patent; THE WALTER AND ELIZA HALL INSTITUTE OF MEDICAL RESEARCH; WO2009/39553; (2009); 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. 61494-55-1, name is 2-(2-Chloropyridin-3-yl)acetic acid, the common compound, a new synthetic route is introduced below. Recommanded Product: 61494-55-1

The solution of lithium diisopropylamide was added via cannula to a rapidly stirred suspension of (2-chloropyridin-3-yl)acetic acid (Intermediate 3; 21.4 g, 125 mmol) in anhydrous THF (400 mL) at O0C. The temperature of the reaction mixture was maintained at O0C over the course of the addition. Upon complete addition of the lithium diisopropylamide solution the resultant bright yellow suspension was stirred at 00C for 15 minutes. A solution of 2-fluoro-4-iodo-l-isothiocyanaobenzene (WO 2007/088345) (34.9 g, 125 mmol) in anhydrous THF (200 mL) was then added to the reaction mixture via cannula and the mixture heated to 650C for 18 hours. The reaction mixture was cooled and the volatiles removed in vacuo. The resultant brown gum was redissolved in THF (200 mL), cooled to O0C and 10% aqueous acetic acid (500 mL) added slowly.Acetonitrile (-200 mL) was added slowly until a brown solid developed; the solid was isolated by filtration and washed with successive portions of diethyl ether and acetonitrile to give the title compound as a yellow crystalline solid (11.0 g, 21%). 5H (DMSO-d6) 8.42 (IH, d, J6.7 Hz), 8.22 (IH, m), 7.73 (IH, m), 7.61 (IH, m), 7.46 (IH, t, J8.6 Hz), 7.35-7.31 (IH, m). Exchangeable protons were not observed. LCMS (pH 10) RT 1.82 minutes, ES+ 415 (M+H)+, ES” 413 (M-H)”.

The synthetic route of 61494-55-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UCB PHARMA S.A.; WO2009/93008; (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. 886365-46-4, name is 5-Chloro-3-methylpyridine-2-carboxylic 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. Safety of 5-Chloro-3-methylpyridine-2-carboxylic acid

General procedure: To a solution of Intermediates 2A and 2B (150 mg, 0.285 mmol) and 5-chloro-3-methylpyridine-2-carboxylic acid (49 mg, 0.285 mmol) in methanol (1 mL) and THF (2 mL) was added 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholin-4-ium chloride (88 mg, 0.300 mmol). The reaction was stirred at RT. After 3 hours, the reaction mixture was partitioned between water and ethyl acetate; the organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated. The residue was redissolved in DCM (5 mL), and TFA (0.44 mL, 5.71 mmol) was added. The reaction was stirred at RT for 2.5 hours, washed with saturated aqueous sodium bicarbonate and brine, and concentrated. The crude product was purified by silica-gel column chromatography, eluting with 2-10% methanol in DCM, to provide the title compound (56 mg, 41% yield). 1H-NMR (400 MHz, DMSO-d6): delta ppm 10.54 (s, 1H), 8.57 (d, J=2.3 Hz, 1H), 8.02-8.06 (m, 2H), 7.85-7.89 (m, 1H), 7.16 (dd, J=11.7, 8.8 Hz, 1H), 5.96 (s, 2H), 3.57 (s, 1H), 2.57 (s, 3H), 2.03-2.14 (m, 1H), 1.89-1.96 (m, 2H), 1.70 (s, 3H), 1.50-1.53 (m, 1H), 1.48 (s, 3H), 1.21-1.35 (m, 2H). LC/MS (ESI+) m/z=479.1 D (M+H).

With the rapid development of chemical substances, we look forward to future research findings about 886365-46-4.

Reference:
Patent; LEWIS, Richard T.; ALLEN, Jennifer R.; BROWN, James; GUZMAN-PEREZ, Angel; HUA, Zihao; JUDD, Ted; LIU, Qingyian; OLIVIERI, Philip R.; ROMERO, Karina; SCHENKEL, Laurie; STELLWAGEN, John; WHITE, Ryan; US2015/38497; (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.98139-15-2, name is 4-Aminopicolinonitrile, molecular formula is C6H5N3, molecular weight is 119.124, as common compound, the synthetic route is as follows.Safety of 4-Aminopicolinonitrile

P0C13 (0.3 mE) was added dropwise to a solution consisting of 1 -(naphthalen- 1 -yl)-5-(trifluoromethyl)-i Hpyrazole-4-carboxylic acid 2b (150 mg, 0.490 mmol), 4-aminopicolinonitrile (64.2 mg, 0.53 9 mmol) and pyridine (5 mE). The mixture was stirred at 0 C. for 1 h. The resulting mixture was concentrated under reduced pressure to give a crude product, which was purified by preparative HPEC (40% to 70% (v/v) ACN and H20 with 0.05% NH3) to afford compound 1. Compound 1 was concentrated to dryness under reduced pressure (101.30 mg, 5 1%). ECMS (ESI): RT=5.45 mm, mass calcd. for C2,H,2F3N50 407.348, mlz found 408.0 [M+H]. ?H NMR (400 MHz, DMSO-d5) oe ppm 11.31 (s, 1H), 8.71 (d, J=5.2 Hz, 1H), 8.56 (s, 1H), 8.30 (s, 1H), 8.26 (d, J=8.0 Hz, 1H), 8.15 (d, J=8.0 Hz, 1H),8.00 (d, J=4.0 Hz, 1H), 7.83-7.77 (m, 1H), 7.76-7.62 (m, 3H), 7.14 (d, J=8.0 Hz, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,98139-15-2, 4-Aminopicolinonitrile, and friends who are interested can also refer to it.

Reference:
Patent; Janssen Biotech, Inc.; Lu, Tianbao; Allison, Brett Douglas; Barbay, Joseph Kent; Connolly, Peter J.; Cummings, Maxwell David; Diels, Gaston; Edwards, James Patrick; Kreutter, Kevin D.; Philippar, Ulrike; Shen, Fang; Thuring, Johannes Wilhelmus John Fitzgerald; Wu, Tongfei; (412 pag.)US2018/170909; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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 886374-01-2, name is 5-Chloro-3-fluoro-2-methoxypyridine. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 886374-01-2

Nitrogen gas was purged through a mixture of 5-chloro-3-fluoro-2-methoxy- pyridine (700 mg, 4.33 1 mmol), bis(pinacolato)diboron (1.32 g, 5.198 mmol) and potassium acetate (1.27 g, 12.993 mmol) in 1,4-dioxane (10 mL) for 30 mm. Then, [1,1-bis- (diphenylphosphino)-feffocene]palladium(II)chloride complex with DCM (353 mg, 0.433 mmol) was added. Nitrogen gas purging was continued for another 5 mm. The reaction mixture was heated at 100 C overnight. The reaction was monitored by LCMS. After completion of reaction, the mixture was cooled to RT, then filtered through a celite bed. The organic solvent was removed under reduced pressure and the residue obtained was triturated with pentane. The pentane layer was taken and concentrated to obtain 1.01 g of 3-fluoro-2- methoxypyridine-5-boronic acid pinacol ester which was used as such for next step without further purification.

With the rapid development of chemical substances, we look forward to future research findings about 886374-01-2.

Reference:
Patent; MEDIVATION TECHNOLOGIES, INC.; RAI, Roopa; CHAKRAVARTY, Sarvajit; GREEN, Michael, John; PHAM, Son, Minh; PUJALA, Brahmam; AGARWAL, Anil, Kumar; NAYAK, Ajan, Kumar; KHARE, Sweta; GUGULOTH, Rambabu; RANDIVE, Nitin, Atmaram; WO2015/58084; (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.67367-24-2, name is Methyl 4-hydroxynicotinate, molecular formula is C7H7NO3, molecular weight is 153.1354, as common compound, the synthetic route is as follows.Safety of Methyl 4-hydroxynicotinate

A solution of the required alcohol (0.30 mmol; 3 eq.) in DMF (0.2 mL), in a glass vial under inert atmosphere (N2), is treated with NaH (3.3 eq.) at rt. After 10 min, it is treated with a solution of the chloride (0.10 mmol; 1 eq.) in DMF (0.8 mL) and the reaction mixture is stirred at rt and monitored by LC-MS. Upon reaction completion, the reaction mixture is either treated with silica gel-supported sulfonic acid (5.0 eq.; Silicycle SiliaBond Tosic Acid; SCX; R60530B; 0.8 mmol/g), shaken 1 h at rt and filtered, or loaded on a corresponding cartridge (Silicycle SiliaPrep Tosic Acid Si-SCX). In both cases, the resin is then washed with DCM, 1:1 DCM/MeOH and MeOH, and the product eventually released from the resin with 7M ammonia solution in MeOH. The solution of crude product is concentrated under reduced pressureand purification of the residue gives the desired product.Example 212 4-[3-(3-ethyl-ureido)-isoquinolin-8-ylmethoxy]-nicotinic acid methyl ester hydrochloride Starting from the compound of Preparation R and methyl 4-hydroxynicotinate and proceeding in analogy to Procedure AC, the title compound was obtained, after purification by prep-HPLC (acidic conditions) and treatment with HCl, as an amorphous solid (21% yield). MS (ESI, m/z): 381.28 [M+H+].

At the same time, in my other blogs, there are other synthetic methods of this type of compound,67367-24-2, Methyl 4-hydroxynicotinate, and friends who are interested can also refer to it.

Reference:
Patent; Bur, Daniel; Gude, Markus; Hubschwerlen, Christian; Panchaud, Philippe; US2013/96119; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 76006-11-6 ,Some common heterocyclic compound, 76006-11-6, molecular formula is C6H4ClN3, 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: Chloro derivative 6 (490 mg, 3.19 mmol) was dissolved into concentrated sulfuric acid (9.50 mL) at 0C and then a mixture ofconcentrated sulfuric acid (0.49 mL) and nitric acid (0.49 mL)was added dropwise into this solution. This reaction mixturewas heated at 95C for 1h. Upon cooling, it was poured intocrashed ice, neutralized with an aqueous solution of NH3 andthe product was extracted with ethyl acetate (3×100 mL). Thecombined organic layers were dried over Na2SO4 and evaporated under reduced pressure to provide 600 mg of pure 7 asa yellow solid.

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. 76006-11-6, 7-Chloro-1H-pyrazolo[3,4-c]pyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Sklepari, Meropi; Lougiakis, Nikolaos; Papastathopoulos, Athanasios; Pouli, Nicole; Marakos, Panagiotis; Myrianthopoulos, Vassilios; Robert, Thomas; Bach, Stephane; Mikros, Emmanuel; Ruchaud, Sandrine; Chemical and Pharmaceutical Bulletin; vol. 65; 1; (2017); p. 66 – 81;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 56826-61-0, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 56826-61-0 as follows.

A solution of methyl 2-methylnicotinate (0.5 g, 3.3 mmol) in THF (16 mL) at 0 C. was treated dropwise with lithium aluminum hydride in THF (6.6 mL, 1 M), stirred at 0 C. for 1.5 hours, treated with ethyl acetate (3 mL), warmed to 25 C., and partitioned between ethyl acetate and saturated NaHCO3. The organic phase was washed with brine, dried over MgSO4, filtered and concentrated. A solution of the residue (0.391 g) in dichloromethane (16 mL) was treated with MnO2 (2 g), stirred at 25 C. for 68 hours, filtered through celite, and the solvent was evaporated to give the title compound (0.303 g, 75% yield), which was used without further purification

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,56826-61-0, its application will become more common.

Reference:
Patent; DeGoey, David A.; Flentge, Charles A.; Flosi, William J.; Grampovnik, David J.; Kempf, Dale J.; Klein, Larry L.; US2005/131017; (2005); 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. 116355-18-1, name is 6-Bromo-7-methylimidazo[1,2-a]pyridine, molecular formula is C8H7BrN2, 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 116355-18-1

The compound of example 146 (8 g, 37.9 mmol) was treated with 6-methylpyridin-3- ylboronic acid (5.71 g, 41 .7 mmol) in the presence of [1 ,1 ‘-Bis(diphenylphosphino)- ferrocene]dichloropalladium(ll) complex with dichloromethane (0.495 g, 0.606 mmol) and sodium carbonate (6.03 g, 56.9 mmol) according to the procedure for the preparation of the compound of example 2 to afford the title compound. Yield: 8.0 g (95 %); 1 H NMR (DMSO-d6, 300 MHz): delta 2.2 (s, 3H, CH3), 2.54 (s, 3H, CH3), 7.35-7.37 (d, 1 H, J=8.1 Hz, Ar), 7.50-7.53 (d, 1 H, J=8.7 Hz Ar), 7.53 (s, 1 H, Ar), 7.76-7.80 (dd, 1 H, J=2.4 Hz & J=5.7 Hz, Ar Ar), 7.8 (s, 1 H, Ar), 8.4 (s, 1 H, Ar), 8.49-8.50 (d, 1 H, J=1 .8 Hz, Ar); MS (ES+): m/e 224.1 (M+1 ).

With the rapid development of chemical substances, we look forward to future research findings about 116355-18-1.

Reference:
Patent; PIRAMAL ENTERPRISES LIMITED; SHARMA, Rajiv; GHOSH, Usha; MORE, Tulsidas; KULKARNI, Mahesh; BAJAJ, Komal; BURUDKAR, Sandeep; RIZVI, Zejah; WO2014/80241; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem