Day: April 18, 2022

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. 122306-01-8, name is (6-Bromopyridin-3-yl)methanol, molecular formula is C6H6BrNO, 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. COA of Formula: C6H6BrNO

To a mechanically-stirred solution of 78.12 g of thionyl chloride in 450 mL of acetonitrile at 15 C. was added a solution of 160.75 g of 3-hydroxymethyl-6-bromopyridine in 446 mL of acetonitrile over 30 minutes. The temperature rose to 22 C. during the addition, and the reaction mixture was stirred for 15 minutes at room temperature. The mixture was cooled in an ice bath, and a solution of 70 g of NaOH in 1.4 L of water was added at such a rate that the temperature did not exceed 15 C. 603 mL of toluene was added to the mixture and stirred rapidly. The layers were separated. The aqueous phase was reextracted with toluene. The combined organic phase was concentrated in vacuo to give 181.61 g of 3-chloromethyl-6-bromopyridine.

With the rapid development of chemical substances, we look forward to future research findings about 122306-01-8.

Reference:
Patent; G. D. Searle & Co.; US5420270; (1995); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 130473-26-6, 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 130473-26-6, name is 1H-Pyrrolo[2,3-c]pyridine-5-carbaldehyde. This compound has unique chemical properties. The synthetic route is as follows.

C174 (500 mg, 3.42 mmol) is dissolved in 1.5 mL formic acid. The solution is cooled to in an ice bath, 30% aqueous hydrogen peroxide (722 muL, 6.8 mmol) is added drop-wise, and the reaction is stirred 1 h in an ice bath, and allowed to stand overnight at 5 C. The mixture is diluted with water, the solid is collected, washed with water and is dried to give 522 mg of an off-white solid. The formate salt is added to 7 mL water, 3 mL 2N NaOH is added, and the pH is adjusted to 3 with 5% aqueous HCl. The precipitate is collected and is dried to afford 1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid (C176) (67% yield). HRMS (FAB) calculated for C8H6N2O2+H: 163.0508, found 163.0507 (M+H)+.

According to the analysis of related databases, 130473-26-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Wishka, Donn G.; Reitz, Steven Charles; Piotrowski, David W.; Groppi JR., Vincent E.; US2003/45540; (2003); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 89364-04-5 ,Some common heterocyclic compound, 89364-04-5, molecular formula is C5H3BrN2O2, 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: 3-(4-bromophenyl)-4-nitropyridine To a stirred solution of 3-bromo-4-nitropyridine (100 g, 492.6 mmol), (4-bromophenyl)boronic acid (98.6 g, 492.6 mmol), and potassium carbonate (203.9 g, 1.47 mol) in toluene (1000 ml)-water (100 ml) was added tetrakis(triphenylphosphine)palladium (14.8 g, 12.8 mmol) at room temperature under nitrogen atmosphere; the mixture was degassed with nitrogen three times. The resulting mixture was stirred at 50 C. overnight. TLC showed the reaction was complete. The solid was removed through filtration and washed with ethyl acetate (100 ml*3). The organic layer was collected and the aqueous layer was extracted with ethyl acetate (100 ml*2). The combined organic layers were washed with brine (400 ml), dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give a crude residue which was purified by silica gel pad (eluted with 10-33% ethyl acetate in hexane) to afford 3-(4-bromophenyl)-4-nitropyridine (89 g, yield 65%) as 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. 89364-04-5, 3-Bromo-4-nitropyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Arvinas, Inc.; Crew, Andrew P.; Berlin, Michael; Flanagan, John J.; Dong, Hanqing; Ishchenko, Alexey; (559 pag.)US2018/125821; (2018); 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. 777931-67-6, name is 3-Bromo-2-chloro-6-methoxypyridine, the common compound, a new synthetic route is introduced below. category: pyridine-derivatives

Into a 100-mL vial maintained with an inert atmosphere of nitrogen, to a solution of 3-bromo-2-chloro-6-methoxypyridine (2.00 g, 8.900 mmol, 1.00 equiv.) in 1,4-dioxane (20 mL), added Pd(dppf)Cl2.CH2Cl2 (0.36 g, 0.450 mmol, 0.05 equiv.), Zn(CH3)2 (17 mL, 17.000 mmol, 2.00 equiv.). The resulting solution was stirred 16 h at 90 C. The mixture was concentrated under vacuum. The residue product was purified by chromatogram on silica gel with ethyl acetate/petroleum ether (2:98) to yield 2-(6-(1-ethyl-4-fluoro-1H-indazol-6-yl)-2-methoxypyridin-3-yl)-3-methylbutanal as yellow oil. Mass spectrum (ESI, m/z): Calculated for C7H8ClNO, 158.0 [M+H], found 157.8.

The synthetic route of 777931-67-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Janssen Pharmaceutica NV; Zhang, Xuqing; Macielag, Mark J.; (179 pag.)US2019/47959; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 578007-66-6 , The common heterocyclic compound, 578007-66-6, name is 5-Bromo-3-iodo-2-methoxypyridine, molecular formula is C6H5BrINO, 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: tert-Butyl (1-(4-((5-bromo-2-methoxypyridin-3- yl)ethynyl)phenyl)cyclobutyl)carbamate: To a degassed solution of 5-bromo-3-iodo-2- methoxypyridine (823 mg, 2.62 mmol) in triethylamine (8.0 mL) at 0 C was added Pd(PfBu3)2 (1 10.4 mg, 6 mol%), Cul (5.0 mg, 1 mol%) and terf-butyl (1-(4- ethynylphenyl)cyclobutyl)carbamate (71 1 mg, 2.62 mmol). The brown suspension was stirred for 56 hours at room temperature before the reaction mixture was suspended in dichloromethane and washed with brine, dried over magnesium sulphate, filtered and concentrated in vacuo. The resulting residue was purified by silica gel chromatography (gradient 10 to 25% EtOAc in hexane) to give the title compound as a white solid (1.04 g, 87%). H-NMR (500 MHz, CDCI3) delta 8.14 (d, 1 H), 7.84 (d, 1 H), 7.52 (dd, 2H), 7.41 (d, 2H), 5.13 (bs, 1 H), 4.01 (s, 3H), 2.50-2.56 (m, 4H), 2.09-2.14 (m, 1 H), 1.84-1.90 (m, 1 H), 1.36 (bs, 9H).

The synthetic route of 578007-66-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ALMAC DISCOVERY LIMITED; BELL, Mark, Peter; O’DOWD, Colin, Roderick; ROUNTREE, James, Samuel, Shane; TREVITT, Graham, Peter; HARRISON, Timothy; MCFARLAND, Mary, Melissa; WO2011/55115; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 33252-28-7, 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.33252-28-7, name is 6-Chloronicotinonitrile, molecular formula is C6H3ClN2, molecular weight is 138.55, as common compound, the synthetic route is as follows.

[N- (5-CYANO-2-PHENYL-LH-PYRROLOF2, 3-BLPYRIDIN-3-YL)-ACETAMIDE] [6-CHLORO-NICOTINONITRILE] (1.38 g, 10 mmol) was dissolved in 1,4-dioxane (50 ml). Hydrazine hydrate (0.525 ml, 10.4 mmol) was added and the resulting solution stirred for 1.5h, whereupon it was concentrated in vacuo. The residue was chromatographed (silica gel, gradient ethyl acetate/heptane from 1: 1 to 1: 0). The slower running component was concentrated in vacuo to afford the 6-hydrazino-nicotinonitrile monohydrate [0.80 g, 53%, APCI-MS m/z: 135.2 [MH+] ]. Part of this hydrazine (67 mg, 0.5 mmol) and [N- (2-OXO-2-] [PHENYL-ETHYL)-ACETAMIDE] (85 mg, 0.5 mmol) were fused together for lh at 230 [C.] The reaction mixture was allowed to cool and the glassy solid suspended in warm dichloromethane/methanol (7: 3 mixture) and then filtered. The solid was further washed with hot [ACETONITRILE/N,] [N-DIMETHYLFORMAMIDE] (9: 1 mixture) and finally acetonitrile. This afforded the title compound as a grey powder (25 mg, 18%). ‘H-NMR (DMSO-d6) : [B] 12.64 [(1H,] s); 9.66 [(1H,] s); 8.62 [(1H,] s); 8.27 (1H, s); 7.84 (2H, d); 7.52 (2H, t); 7.42 [(1H,] t); 2.10 (3H, s). [‘3C-NMR] (DMSO-d6) : [8] 147.3 ; 145.8 ; 134.0 ; 131.5 ; 129.9 ; 128.8 ; 128.7 ; 127.5 ; 118.8 ; 117.6 ; 110.1 ; 99.9 ; [22. 7.] APCI-MS m/z : 277.1 [[MH+].]

The chemical industry reduces the impact on the environment during synthesis 33252-28-7, I believe this compound will play a more active role in future production and life.

Reference:
Patent; ASTRAZENECA AB; WO2004/16609; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 72587-18-9, 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 72587-18-9 as follows.

6-chloro-3- (ethanesulfonyl) pyridin-2-carboxylic acid 2.50 g, and the mixture of thionyl chloride 1.31g of toluene 30 mL, and DMF1 drop was heated under reflux for 3 hours. The reaction mixture was concentrated and dissolved in tetrahydrofuran 30 mL, under ice-cooling, 3-amino-2-chloro-5- (trifluoromethyl) pyridine 1.97 g, triethylamine 1.10g was added dropwise respectively. After stirring for 3 hours at room temperature, The reaction mixture was added to ice water, and extracted with ethyl acetate. The resulting organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated. The residue was subjected to silica gel column chromatography, described below 6-chloro-3- (ethanesulfonyl) – [2-chloro-5- (trifluoromethyl) pyridin-3-yl] pyridine-2-carboxamide 2.4g It was obtained.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,72587-18-9, its application will become more common.

Reference:
Patent; SUMITOMO CHEMICAL COMPANY LIMITED; NAKAJIMA, YUJI; OKAWARA, YUICHI; (263 pag.)JP2016/102104; (2016); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1201187-18-9, 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. 1201187-18-9, name is 6-Chloro-4-(trifluoromethyl)nicotinonitrile. A new synthetic method of this compound is introduced below.

4-hydroxy was prepared in Reference Example 60 3- (piperidin-4-yl) -4- (trifluoromethyl) -1,4,5,7- tetrahydro -6H- pyrazolo [3,4-b] pyridin-6-one hydrochloride (150mg, 0.440mmol) in dimethyl sulfoxide (0.5 mL) solution of, N, N- diisopropylethylamine (89.8muL, 0.528mmol), and 6-fluoro-3- ( the compounds described in trifluoromethyl) pyridine-2-carbonitrile (US2008 / 275057 pamphlet, 136mg, 0.660mmol) was added, using a Biotage Inc. the Initiator (TM), 60 C., 20 min micro and the mixture was stirred while irradiating the waves.The reaction mixture was poured into water, and extracted twice with ethyl acetate, the resulting organic layer was washed successively with water and saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure.The resulting residue was purified by silica gel column chromatography was purified in the elution solvent hexane / ethyl acetate = 88 / 12-0 / 10 gradient)], the title compound (43.1mg, yield: 21%) a.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1201187-18-9, 6-Chloro-4-(trifluoromethyl)nicotinonitrile, and friends who are interested can also refer to it.

Reference:
Patent; Daiichi Sankyo company limited; Sato, Rie; Kobayashi, Katsuhiro; Kaneko, Toshio; (188 pag.)JP2015/113323; (2015); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 7477-10-3, 6-Chloro-5-nitronicotinic 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, Application In Synthesis of 6-Chloro-5-nitronicotinic acid, blongs to pyridine-derivatives compound. Application In Synthesis of 6-Chloro-5-nitronicotinic acid

General procedure: SI, Figure 1. General procedure for the synthesis of the ester compounds (2, Scheme 1). To the commercially available acids (1a-c) (1 equiv.) in dry DCM (20 mL) was added DMAP (1 equiv.),DCC (1.2 equiv.) and various alcohols (1.2 equiv.) at 0 oC. The mixture was stirred at 0 oC for 1h then at room temperature for 17 h. The solvent was evaporated and the residue was purified by flash column chromatography on silica gel using a mixture of solvent of hexane: ethylacetate (10:1) to provide the desired ester derivatives(2).

The synthetic route of 7477-10-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Iniguez, Eva A.; Perez, Andrea; Maldonado, Rosa A.; Skouta, Rachid; Bioorganic and Medicinal Chemistry Letters; vol. 25; 22; (2015); p. 5315 – 5320;,
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. 49669-13-8, name is 2-Acetyl-6-bromopyridine. A new synthetic method of this compound is introduced below., Application In Synthesis of 2-Acetyl-6-bromopyridine

Preparation 31 Synthesis of 2-(6-bromo-pyridin-2-yl)-propan-2-ol Add a solution of methyl magnesium bromide (3.0 M, 9.7 mL, 29.09 mmol) in tetrahydrofuran dropwise over 20 min to a cooled solution of 1-(6-bromo-pyridin-2-yl)-ethanone (5 g, 24.25 mmol) in anhydrous tetrahydrofuran (48.5 mL) at 0 C. Upon completion of the reaction, add water (exothermic), dilute with ethyl acetate (50 mL) and separate the layers. Extract the aqueous layer once with ethyl acetate (50 mL). Dry the combined organic layers over sodium sulfate, filter and concentrate to give the title compound as a pale yellow liquid (5.69 g, 98%) that is used without further purification. 1H NMR (CDCl3) delta 1.55 (s, 6H), 4.07 (s, 1H), 6.59 (t, 1H), 7.37 (t, 2H), 7.55 (t, 1H).

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, 49669-13-8, 2-Acetyl-6-bromopyridine.

Reference:
Patent; Britton, Thomas Charles; Dehlinger, Veronique; Fivush, Adam Michael; Hollinshead, Sean Patrick; Vokits, Benjamin Paul; US2009/253750; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem