Tag: M.W:100-200

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 13958-98-0, name is 3-Bromo-4-cyanopyridine. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 13958-98-0

Step A: Preparation of 2-phenylthieno[2,3-c]pyridin-3-amine: A mixture of benzyl mercaptan (0.2719 g, 2.19 mmol, 1.0 equiv.) and DMF (3 mL) was stirred at room temperature, and NaOMe (250 mg, 2.1 equiv) was added. The solution was stirred for 5 minutes, and then 3-bromoisonicotinonitrile (400 mg, 1.0 equiv.) was added directly to the solution. The reaction mixture was stirred overnight at room temperature, then the volatiles were removed via rotary evaporation. Water was added, and the reaction mixture was extracted twice with ether. The combined organic layers were dried (Na2SO4) and purified by silica gel chromatography (eluting first with 100% Et2O to remove non-polar impurities, then switching to a CHCl3/MeOH gradient) to afford 221 mg (45%) of the desired product.

With the rapid development of chemical substances, we look forward to future research findings about 13958-98-0.

Reference:
Patent; Miknis, Greg; Lyssikatos, Joseph P.; Laird, Ellen; Tarlton, Eugene; Buckmelter, Alexandre J.; Ren, Li; Rast, Bryson; Schlacter, Stephen T.; Wenglowsky, Steven Mark; US2007/49603; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 22245-83-6, 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. 22245-83-6, name is 3-(Trifluoromethyl)pyridin-2-ol. A new synthetic method of this compound is introduced below.

EXAMPLE 12APreparation of compound 2003Step 1 :To a mixture of 2-hydroxy-3-triotafluoromethylpyridine 12a1 (39.01 g, 239 mmol) and anhydrous DMF (800 ml_) under Ar is added lambda/-iodosuccinimiotade (4.89 g, 244 mmol) and anhydrous K2CO3 (33.72 g, 244 mmol) and the mixture is allowed to stir at 600C for about 3 hours. The mixture is cooled to ambient temperature, filtered and concentrated under reduced pressure. The residue is dissolved in DCM (1 L) and the organic phase is washed with brine The aqueous phase is adjusted to pH 4 by the addition of 2 M HCI then extracted with DCM (1 L). The combined organic extracts are washed with brine (2 L) and dried over Na2SO4 The mixture is concentrated to ~300 mL and cooled overnight in a fridge. The precipitated solid is removed by filtration and dried to provide aryl iodide 12a2

At the same time, in my other blogs, there are other synthetic methods of this type of compound,22245-83-6, 3-(Trifluoromethyl)pyridin-2-ol, and friends who are interested can also refer to it.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; WO2009/18657; (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. 13466-43-8, name is 3-Bromopyridin-2(1H)-one, the common compound, a new synthetic route is introduced below. Recommanded Product: 13466-43-8

Methyl iodide (1.5 mL, 24.14 mmol) was added to a suspension of potassium carbonate (1668 mg, 12.07 mmol), TBAI (89 mg, 0.24 mmol) and 3-bromopyridin-2-ol (420 mg,2.4 14 mmol) in toluene (15 mL). The reaction mixture was heated to 40 C for 17 hours. The mixture was partitioned between DCM and water and the combined extracts dried (hydrophobic fit) and concentrated in vacuo. The crude product was purified by column chromatography on silica, eluted with 0-70% petrol/ethyl acetate to afford 3 -bromo- 1- methylpyridin-2(1H)-one, Intermediate 5 (390 mg, 86 %).?H NMR (400 MHz, DMSO-d6) & 3.50 (s, 3 H) 6.17 (t, J=7.07 Hz, 1 H) 7.78 (dd, J=6.82,1.77 Hz, 1 H) 7.90 (dd, J=7.33, 1.77 Hz, 1 H)

The synthetic route of 13466-43-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; TAKEDA CAMBRIDGE LIMITED; LIVERMORE, David; WHITE, Kathryn; CONGREVE, Miles; BROWN, Giles; O’BRIEN, Michael; WO2014/122474; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 18368-76-8, 2-Chloro 3-methylpyridine, 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, Safety of 2-Chloro 3-methylpyridine, blongs to pyridine-derivatives compound. Safety of 2-Chloro 3-methylpyridine

The compound 5 (1 mmol),The compound 2-chloro-3-methylpyridine (1 mmol)Dissolved in NMP (10 mL)CuI (20 mmolpercent) was added,Pd (PPh3) 2Cl2 (5 mmolpercent),DIEA (5 mmol).Under nitrogen protection,60 reaction 12h.TCL monitoring reaction is complete,Extracted three times with ethyl acetate,Combine organic phase,Washed twice with saturated NaCl,Anhydrous Na2SO4 dry.Spin dry,Column chromatography gave compound 7j.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,18368-76-8, 2-Chloro 3-methylpyridine, and friends who are interested can also refer to it.

Reference:
Patent; Second Military Medical University, PLA; Yantai Dongcheng Pharmaceutical Industry Group Co., Ltd.; Zhang, Dazhi; Jiang, Yuanying; Niting, Junhong; Cai, Zhan; Pang, Lei; Xie, Fei; Li, Ran; Han, Haibing; He, Yan; You, Shouyi; Yang, Zhenqiu; Qi, Dongqi; (36 pag.)CN106336383; (2017); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 16830-24-3 , The common heterocyclic compound, 16830-24-3, name is Methyl 2-methylisonicotinate, molecular formula is C8H9NO2, 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.

The remaining solid is washed with diethyl ether and dried to give methyl 2-methyl-pyridine-4-carboxylate; LC-MS: tR=0.39 min, [M+1]+=152.05. This material is dissolved in 7 N NH3 in methanol (25 mL) and the mixture is stirred in a sealed vial for 20 h at 60 C. before it is filtered. The filtrate is evaporated to give crude 2-methyl-isonicotinamide (2.12 g) as a brownish solid.

The synthetic route of 16830-24-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bolli, Martin; Lescop, Cyrille; Mathys, Boris; Mueller, Claus; Nayler, Oliver; Steiner, Beat; Velker, Jorg; US2011/212998; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 13228-40-5, 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. 13228-40-5, name is 2-(2-Pyridyl)indole. A new synthetic method of this compound is introduced below.

Step 3: To a solution of 16 (1.6 g, 8.24 [MMOL) IN ACOH] (30 ml) at 80 [C] was added 4-piperidone hydrochloride (3.7 g, 23.9 [MMOL)] and [H3PO4] (10 [ML).] The reaction was stirred at this temperature for 72 h and at [100] C for 24 h. The reaction was cooled to RT and poured into [ICE/NH40H] and extracted with EtOAc. The combined organic layers were washed with water and brine, dried [(NA2SO4)] and concentrated. The residue was purified on a flash column (20% EtOAc in hexane to 10% CH30H/NH3 in [CH2CI2)] to give 17 (0.5 g, 44% based on recovered starting material). MS (M+H) [=] 276.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,13228-40-5, its application will become more common.

Reference:
Patent; SCHERING CORPORATION; WO2004/831; (2003); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 62068-78-4, 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. 62068-78-4, name is 2,6-Dichloronicotinamide, molecular formula is C6H4Cl2N2O, 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.

6-Chloro-2-(2-methoxy-ethylamino)-nicotinamide (2) (1113) Refer to synthesis of D46 for preparation of 2,6-dichloro-nicotinamide (1). A sealed reaction vessel containing 2,6-dichloro-nicotinamide (1) (8.66 g, 45.3 mmol) and 2-methoxy-ethylamine (15.6 mL, 181 mmol) in anhydrous dimethylformamide (40 mL) was heated to 60 C. for 7 h. The reaction was then cooled to room temperature. Dimethylformamide was azeotropically removed by the addition and evaporation of toluene (6×700 mL) by rotary evaporation with water bath at 70 C. An orange oil was obtained (12.2 g). The oil was fractionated by dry-pack column chromatography as follows: the oil was diluted with CH2Cl2 (400 mL) followed by the addition of silica gel (100 g, 230-400 mesh) and concentrated to dryness. This was loaded onto a silica column (200 g, 230-400 mesh) and eluted with 50% EtOAc/hexanes. Pure fractions were combined and concentrated to give the title compound as a white solid (5.37 g, 64% isolated yield). 1H NMR 400 MHz (d6-DMSO) delta7.79 (d, J=7.8 Hz, 1H), 7.30 (s, 1H), 6.76 (d, J=7.8 Hz, 1H), 6.52 (s, 1H), 4.04 (br t, J=4.7 Hz, 1H), 3.80 (td, J=5.5, 4.7 Hz, 2H), 3.63 (t, J=5.5 Hz, 2H), 2.94 (s, 3H).

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 62068-78-4, 2,6-Dichloronicotinamide.

Reference:
Patent; ANACOR PHARMACEUTICALS, INC.; AKAMA, Tsutomu; US2015/291629; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 63071-13-6, 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.63071-13-6, name is 4-Chloropicolinaldehyde, molecular formula is C6H4ClNO, molecular weight is 141.56, as common compound, the synthetic route is as follows.

Step 1. Preparation of 4-(2-((1R,2R)-2-hydroxycyclohexylamino)benzo[d]thiazol-6-yloxy)picolinaldehyde To the reaction mixture of 2-((1R,2R)-2-hydroxycyclohexylamino)benzo[d]thiazol-6-ol (90 mg, 0.34 mmol) in 1.9 ml of NMP was added Cesium Carbonate (232 mg, 0.71 mmol) and 4-chloropicolinaldehyde (125 mg, 0.883 mmol). The reaction mixture was stirred at RT. for 10 minutes and then microwaved at 150 C. for 750 seconds. The crude reaction mixture was filtered, purified on prep HPLC and lyophilized to give 4-(2-((1R,2R)-2-hydroxycyclohexylamino)benzo[d]thiazol-6-yloxy)picolinaldehyde as TFA salt (88 mg). ES/MS m/z 388.1 (MH+) as the hydrate (+18).

The chemical industry reduces the impact on the environment during synthesis 63071-13-6, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Novartis AG; US2008/45528; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 884494-73-9 ,Some common heterocyclic compound, 884494-73-9, molecular formula is C7H6FNO2, 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: A solution of 4-(6-(3 ,6-diazabicyclo[3. 1.1 ]heptan-3 -yl)pyridin-3 -yl)-6-(2- hydroxy-2-methylpropoxy)pyrazolo[ 1,5 -a]pyridine-3 -carbonitrile dihydrochloride (Intermediate P43; 30mg, 0.063 mmol), in DCM (1 mL) was treated with DIEA (27 tL, 0.16 mmol) and stirred for 5 mm at ambient temperature. The resulting mixture was treated sequentially with 5-chloro- 6-methoxynicotinaldehyde (11 mg, 0.063 mmol) and NaBH(AcO)3 (27 mg, 0.13 mmol). After stirring 12 h at ambient temperature, the reaction mixture was diluted with DCM and washed with 10% Na2CO3(aq). The combined organic extracts were dried over anhydrous MgSO4(), filtered, and concentrated in vacuo. The residue was purified by silica chromatography (10% MeOHI DCM with 1% NH4OH as the eluent) to cleanly provide the title compound (22 mg, 63% yield). MS (apci) m/z = 560.3 (M+H).

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. 884494-73-9, 5-Fluoro-6-methoxynicotinaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ANDREWS, Steven W.; ARONOW, Sean; BLAKE, James F.; BRANDHUBER, Barbara J.; COOK, Adam; HAAS, Julia; JIANG, Yutong; KOLAKOWSKI, Gabrielle R.; MCFADDIN, Elizabeth A.; MCKENNEY, Megan L.; MCNULTY, Oren T.; METCALF, Andrew T.; MORENO, David A.; TANG, Tony P.; REN, Li; (668 pag.)WO2018/71447; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 6188-23-4, 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 6188-23-4 as follows.

To a solution of 6-bromoimidazo[1,2-a]pyridine (318 mg, 1.61 mmol) in 1,4-dioxane (15 mL) were added N-(2-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)cyclopropanesulfonamide (600 mg, 1.69 mmol), KOAc (316 mg, 3.22 mmol), H2O (3 mL) and Pd(dppf)Cl2.CH2Cl2 (131 mg, 0.161 mmol). The reaction was heated to 85 C. and stirred further for 5 hours under N2 atmosphere, then cooled to rt, and concentrated in vacuo. The residue was dissolved in DCM (200 mL) and the resulted mixture was filtered through a CELITE. The filtrate was washed with H2O (100 mL) and brine (100 mL). The combined aqueous layers were extracted with DCM (50 mL*3). The combined organic extracts were dried over anhydrous Na2SO4, and concentrated in vacuo. The residue was purified by a flash silica gel column chromatography (DCM/MeOH (v/v)=65/1) to give the title compound as a yellowish solid (342 mg, 62%). MS (ESI, pos. ion) m/z: 345.0 [M+H]+; 1H NMR (600 MHz, DMSO-d6): delta 9.42 (s, 1H), 8.91 (s, 1H), 8.35 (d, J=2.1 Hz, 1H), 7.99 (s, 1H), 7.93 (d, J=2.4 Hz, 1H), 7.68-7.61 (m, 2H), 7.54 (dd, J=1.8, 9.6 Hz, 1H), 3.98 (s, 3H), 2.82-2.74 (m, 1H), 1.00-0.89 (m, 4H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,6188-23-4, its application will become more common.

Reference:
Patent; Calitor Sciences, LLC; Xi, Ning; US2014/134133; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem