Tag: M.W:200-300

Synthetic Route of 886365-06-6, Adding some certain compound to certain chemical reactions, such as: 886365-06-6, name is Methyl 5-bromo-4-methylpicolinate,molecular formula is C8H8BrNO2, 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 886365-06-6.

To 5-Bromo-4-methyl-pyridine-2-carboxylic acid methyl ester (200 mg, 0.869 mmol) and methylamine (135 mg, 11.34 mmol) was added (CH3)3Al (0.6 mg, 0.008 mmol). The mixture was placed in a sealed tube and heated at 100 C. for 1 h, after which the mixture was cooled, quenched with water, and extracted with EtOAc. The organic phase was dried, concentrated, and purified by column chromatograph to give 5-Bromo-4-methyl-pyridine-2-carboxylic acid methylamide (130 mg, 65%) as an off-white 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. 886365-06-6, Methyl 5-bromo-4-methylpicolinate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Hoffmann-La Roche Inc.; Alam, Muzaffar; Du Bois, Daisy Jo; Hawley, Ronald Charles; Minatti, Ana Elena; Kennedy-Smith, Joshua; Thakkar, Kshitij Chhabilbhai; Wilhelm, Robert Stephen; US2013/158066; (2013); 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 228410-90-0, name is 5-bromo-2-hydroxy-3-nitro-4-picoline. This compound has unique chemical properties. The synthetic route is as follows. category: pyridine-derivatives

Step 1. 5-Bromo-1,4-dimethyl-3-nitropyridin-2(1H)-one A solution of 5-bromo-4-methyl-3-nitropyridin-2-ol (15.00 g, 64.37 mmol) [Combi-Blocks, AN-1086] in N,N-dimethylformamide (250 mL) was treated with sodium hydride (3.09 g, 77.3 mmol) (60% dispersion on mineral oil) slowly and portionwise, and stirred at RT for 30 min. The reaction mixture was treated with methyl iodide (4.81 mL, 77.2 mmol) dropwise and stirred at RT for 3 h. LCMS indicated a clean peak for methylated product. The reaction mixture was poured over water/ice (?400 mL) and allowed to stir while the ice melted. The aqueous mixture was extracted with ethyl acetate. The organic layer was washed with water (3*) and brine, dried with magnesium sulfate, filtered, and concentrated to give the desired product (14.9 g, 93%) that was used without further purification. LCMS calculated for C7H8BrN2O3 (M+H)+: m/z=247.0, 249.0. found: 247.0, 248.9.

With the rapid development of chemical substances, we look forward to future research findings about 228410-90-0.

Reference:
Patent; INCYTE CORPORATION; Yue, Eddy W.; Combs, Andrew P.; Douty, Brent; US2015/148342; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 23056-47-5 ,Some common heterocyclic compound, 23056-47-5, molecular formula is C6H5BrN2O2, 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.

25.0 g (115.2 mM) of 2-bromo-4-methyl-5-nitropyridine, 44.3 g (230 mM) of methyl fluorosulfonyldifluoroacetate and 17.6 g (92.2 mM) of CuI were suspended in 250 mL of DMF. This reaction mixture was stirred at 120 C. for 48 hours. The medium was cooled and then diluted with 1000 mL of saturated ammonium chloride solution and 100 mL of ammonium hydroxide, and then stirred until homogenized. The product was extracted three times with ethyl acetate. The residue was purified by chromatography on silica gel, using 95/5 and then 90/10 (v/v) cyclohexane/ethyl acetate as eluent. The fractions containing the expected product were combined and concentrated under reduced pressure. The title product was obtained in the form of a brown oil (8.0 g, yield=34%).1H NMR (300 MHz, DMSO) delta=9.29 (s, 1H), 8.21 (s, 1H), 2.68 (s, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,23056-47-5, its application will become more common.

Reference:
Patent; Laboratoires Fournier SA; US2012/302560; (2012); 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.28733-43-9, name is 5-Bromonicotinamide, molecular formula is C6H5BrN2O, molecular weight is 201.02, as common compound, the synthetic route is as follows.name: 5-Bromonicotinamide

Example 23B 3-amino-5-bromopyridine A solution of 3M NaOH (250 mL) at room temperature was treated with bromine (25.9 g, 162 mmol), stirred for 15 minutes, treated with 5-bromonicotinamide (25 g, 124 mmol), stirred for 45 minutes, heated to 85-100 C. for 3 hours, cooled to room temperature, adjusted to pH 1 with 10% HCl (aq.) washed twice with diethyl ether. The aqueous layer was adjusted to pH~10-11 with solid NaOH, and extracted four times with diethyl ether and twice with dichloromethane. The combined extracts were dried (MgSO4), filtered, and concentrated to provide the desired product (13.3 g, 62%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,28733-43-9, 5-Bromonicotinamide, and friends who are interested can also refer to it.

Reference:
Patent; Li, Qun; Woods, Keith W.; Zhu, Gui-Dong; Fischer, John P.; Gong, Jianchun; Li, Tongmei; Gandhi, Virajkumar; Thomas, Sheela A.; Packard, Garrick K.; Song, Xiaohong; Abrams, Jason N.; Diebold, Robert B.; Dinges, Jurgen; Hutchins, Charles W.; Stoll, Vincent S.; Rosenberg, Saul H.; Giranda, Vincent L.; US2003/199511; (2003); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 179687-79-7, 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 179687-79-7 as follows.

2-(2-Chloro-4-nitro-phenoxymethyl)-pyridine (8 g, 30.2 mmol, 1 equiv) and 8.44 g iron (151.1 mmol, 5 equiv) in 100 mL acetic acid and 50 mL EtOAc were stirred at rt overnight. The reaction mixture was filtered through a pad of Celite. The filtrate was concentrated in vacuo and neutralized with saturated Na2CO3 solution. The solution was EPO extracted with EtOAc and the organic layer was washed with brine and concentrated in vacuo. The resulting crude material was purified by flash chromatography eluting with EtOAc/hexane (3:7) to give 3-chloro-4-(pyridin-2-ylmethoxy)-phenylamine (3.2 g, 52%) as a white solid. 1H-NMR (CDCl3) delta 5.18 (s, 2H), 6.50 (dd, IH)5 6.76 (d, IH),. 6.80 (d, IH), 7.22 (m, IH), 7.64 (d, IH), 7.73 (td, IH), 8.55 (m, IH); LCMS RT = 0.89 min; [M+H]+ = 235.1.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,179687-79-7, its application will become more common.

Reference:
Patent; BAYER PHARMACEUTICALS CORPORATION; WO2006/55268; (2006); A2;,
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. 60010-03-9, name is 2,6-Dichloro-4-methyl-3-nitropyridine, molecular formula is C6H4Cl2N2O2, 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: 2,6-Dichloro-4-methyl-3-nitropyridine

Cyclopropylmethylamine (8.4 mmol, 0.72 mL, ) was added drop-wise to a solution of 3-nitro-2,6- dichloropyridine (-4.8 mmol, 1.32 g at -75% purity) in THF (10 mL) . The resulting solution was stirred at room temperature for 18 hours. Additional (1272) cyclopropylmethylamine (2.7 mmol, 0.23 mL) was added and the reaction mixture was stirred for 18 hours. The yellow suspension was diluted with ethyl acetate and the solution was washed with saturated sodium hydrogen carbonate solution, dried ( gS04) and evaporated to afford the crude title compound as yellow oil (1.35 g) which was used without further purification.

With the rapid development of chemical substances, we look forward to future research findings about 60010-03-9.

Reference:
Patent; ONO PHARMACEUTICAL CO., LTD.; SAITO, Tetsuji; HIGASHINO, Masato; KAWAHARADA, Soichi; LEWIS, Arwel; CHAMBERS, Mark Stuart; RAE, Alastair; HIRST, Kim Louise; HARTLEY, Charles David; WO2015/115673; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 75806-86-9, Adding some certain compound to certain chemical reactions, such as: 75806-86-9, name is 2-Bromo-5-chloro-3-nitropyridine,molecular formula is C5H2BrClN2O2, 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 75806-86-9.

Example 121 : 5-Chloro-3-(4-chloro-3- (trifluoromethyl)phenylsulfonamido)picolinic acid; [00525] Step 1 : A dry 250 mL flask was charged with 2-bromo-5-chloro-3- nitropyridine (24 g, 10 mmol), CuCN (19 g, 20 mmol) and DMF (100 mL). The resultant mixture was stirred at 110 C for 2 h and then concentrated under reduced pressure. Water (100 mL) was added and the aqueous layer was extracted with EtOAc (250 mL X 3). The combined organic layer was washed with brine, dried (MgSO4), and evaporated in vacuo to afford a light yellow solid (15 g) which was used directly for the next step.

According to the analysis of related databases, 75806-86-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CHEMOCENTRYX, INC.; WO2006/76644; (2006); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 944900-06-5, 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.944900-06-5, name is 2-Chloro-6-(trifluoromethyl)nicotinaldehyde, molecular formula is C7H3ClF3NO, molecular weight is 209.55, as common compound, the synthetic route is as follows.

A mixture of 2-chloro-6-(trifluoromethyl)pyridine-3-carbaldehyde 8 (19.0 g, 90.8 mmol), Ti(OEt)4 (41.4 g, 182 mmol), and (S)-(-)-tert-butylsulfinamide (11.2 g, 92.6 mmol) in THF (200 mL) was stirred at reflux for 5 h. The cooled reaction mixture was concentrated, and dissolved in AcOEt (500 mL). The resulting suspension was filtered through a Celite pad, and the filtrate was concentrated and purified by column chromatography (hexane/AcOEt = 4:1) to provide the imine (28.9 g, 99%) as a light yellow solid. 1H NMR (CDCl3) delta: 9.00 (1H, s), 8.53 (1H, d, J = 7.8 Hz), 7.73 (1H, d, J = 7.8 Hz), 1.29 (9H, s). A mixture of the imine (28.9 g, 90.0 mmol), allyl bromide (55.9 g, 0.46 mol), and indium (42.5 g, 0.37 mol) was vigorously stirred in saturated NaBr aq at room temperature for 21 h. After addition of saturated NaHCO3 aq (500 mL), the reaction mixture was extracted with AcOEt (250 mL * 3). The organic layers were filtered through a Celite pad, and dried (Na2SO4), concentrated and purified by column chromatography (hexane/AcOEt = 1:4 with 5% of Et3N) to provide 12 as a colorless solid (30.7 g, 94%). 1H NMR (CDCl3) delta: 7.95 (1H, d, J = 7.8 Hz), 7.64 (1H, d, J = 7.8 Hz), 5.79-5.68 (1H, m), 5.24 (2H, t, J = 14.1 Hz), 5.03-4.99 (1H, m), 3.78 (1H, s), 2.79-2.73 (1H, m), 2.51-2.43 (1H, m), 1.24 (9H, s).

The chemical industry reduces the impact on the environment during synthesis 944900-06-5, I believe this compound will play a more active role in future production and life.

Reference:
Article; Matsufuji, Tetsuyoshi; Shimada, Kousei; Kobayashi, Shozo; Ichikawa, Masanori; Kawamura, Asuka; Fujimoto, Teppei; Arita, Tsuyoshi; Hara, Takashi; Konishi, Masahiro; Abe-Ohya, Rie; Izumi, Masanori; Sogawa, Yoshitaka; Nagai, Yoko; Yoshida, Kazuhiro; Abe, Yasuyuki; Kimura, Takako; Takahashi, Hisashi; Bioorganic and Medicinal Chemistry; vol. 23; 1; (2015); p. 89 – 104;,
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.951625-93-7, name is Methyl 4-chloro-1H-pyrrolo[2,3-b]pyridine-5-carboxylate, molecular formula is C9H7ClN2O2, molecular weight is 210.62, as common compound, the synthetic route is as follows.SDS of cas: 951625-93-7

A suspension of 1 equivalent of compound 15 and 10 equivalents of phenyl hydrazine was heated to 90 C. for 16 hours. Water was added to the reaction mixture at room temperature and decanted to remove the excess phenyl hydrazine. The crude reaction mixture was dissolved in MeOH and 0.1 N NaOH (2:1, 0.033 M) and stirred for 3.5 hours before concentrating to dryness. Purification by column chromatography afforded the title compound 16 as a yellow solid. 1H NMR (400 MHz, DMSO-d6) delta ppm 6.43-6.72 (m, 1H) 7.04-7.28 (m, 1H) 7.37-7.56 (m, 4H) 7.84-8.13 (m, 2H) 8.33-8.55 (m, 1H) 11.99 (s, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,951625-93-7, Methyl 4-chloro-1H-pyrrolo[2,3-b]pyridine-5-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; Helicon Therapeutics, Inc.; US2012/95016; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 823221-93-8, name is 5-Bromo-2-chloro-4-(trifluoromethyl)pyridine. This compound has unique chemical properties. The synthetic route is as follows. HPLC of Formula: C6H2BrClF3N

Step C. (1 S, 1 aS,6aR)-4-((5-(6-chloro-4-(trifluoromethyl)pyridin-3-yl)-2-fluorobenzyl)oxy)- l, la,6,6a-tetrahvdrocyclopropara1indene-l -carboxylic acid, ethyl ester 5-Bromo-2-chloro-4-(trifluoromethyl)pyridine (974 mg, 3.74 mmol) was added to a solution of (l S,laS,6aR)-4-((2-fluoro-5-(4,4,5,5-tetramethyl- l,3,2-dioxaborolan-2- yl)benzyl)oxy)-l, la,6,6a-tetrahydrocyclopropa[a]indene-l -carboxylic acid, ethyl ester (1.583 g, 3.5 mmol) in DME (20 ml) under N2, followed by potassium carbonate (2.43 g, 17.58 mmol) and l,l’-bis(diphenylphosphino)ferrocene-palladium(ii)dichloride dichloromethane complex (35 mg, 0.043 mmol). The mixture was heated at 90C overnight. It was poured into saturated NH4CI solution and extracted with EtOAc (lx). The organic phase was washed with brine, dried (MgS04), filtered and the solvent evaporated. The residue was purified on silica gel using hexane and to give the title compound. MS m/e: (M+H)+ 506, 508.

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, 823221-93-8, 5-Bromo-2-chloro-4-(trifluoromethyl)pyridine.

Reference:
Patent; MERCK SHARP & DOHME CORP.; HAGMANN, William K.; LI, Bing; SZEWCZYK, Jason W.; WANG, Bowei; PARKER, Dann; BLIZZARD, Timothy; JOSIEN, Hubert; BIJU, Purakkattle; CHOBANIAN, Harry; GUDE, Candido; NARGUND, Ravi P.; PIO, Barbara; DANG, Qun; LIN, Linus S.; HU, Bin; CUI, Mingxiang; CHEN, Zhengxia; DAI, Meibi; ZHANG, Zaihong; LV, Ying; TIAN, Lili; WO2015/89809; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem