Day: April 8, 2022

Synthetic Route of 73583-41-2, 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 73583-41-2, name is 4-Bromo-3-chloropyridine. This compound has unique chemical properties. The synthetic route is as follows.

EXAMPLE 01-51 Preparation of 3-[(3-chloropyridin-4-yl)amino]-2-methylcyclohex-2-en-l-one (01-51): 3- amino-2-methylcyclohex-2-enone (500 mg, 4 mmol), 4-bromo-3-chloropyridine (950 mg, 5 mmol), palladium acetate (90 mg, 0.4 mmol), BINAP (197 mg, 0.8 mmol), cesium carbonate (2.6 g, 8 mmol) and toluene (10 mL) were combined in a sealed flask and heated at 100C, for 18 h. At rt, the mixture was filtered and the filtrate was diluted with EtOAc (30 mL), washed with brine (3 x 10 mL), dried with Na2S04. The crude was purified by HPLC to afford the title compound (140 mg, 15% yield, white microcrystal, mp = 135-138C). 1H NMR (D6-DMSO) delta 1.46 (s, 3H), 1.83-1.88 (m, 2H), 2.31 (t, J= 6.7 Hz, 2H), 2.53-2.57 (m, 2H), 6.84 (d, J= 6.1 Hz, 1H), 8.06 (s, 1H), 8.29 (d, J= 6.1 Hz, 1H), 8.48 (s, 1H). 13C NMR (D6-DMSO) delta 10.9, 20.6, 28.7, 36.7, 115.7, 117.1, 121.2, 144.7, 148.3, 148.3, 149.2, 154.4, 197.0. LCMS t = 1.9 min, m/z Calcd for Ci2Hi4ClN20; Ci2Hi3ClN2NaO 237.080; 259.061 [M+H]+; [2M+H]+, Found 237.080; 259.180.

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 73583-41-2, 4-Bromo-3-chloropyridine.

Reference:
Patent; ICAHN SCHOOL OF MEDICINE AT MOUNT SINAI; ZHOU, Ming-Ming; OHLMEYER, Michael; VINCEK, Adam; ZAWARE, Nilesh; WO2015/31824; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1214328-96-7, 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 1214328-96-7, name is Methyl 3-bromo-6-chloropicolinate. This compound has unique chemical properties. The synthetic route is as follows.

EXAMPLE 2 Synthesis of 3-bromo-4,6-dichloro-pyridine-2-carboxylic acid methyl ester.2.1 Preparation of 3-bromo-6-chloro-pyridine-2-carboxylic acid N-oxideUrea hydrogen peroxide (65.32 g, 347.2 mmol) was added portionwise to a solution of trifluoroacetic anhydride (145.8 g, 694.4 mmol, 96.5 mL) in dichloromethane (577 mL) at 0 C. 3-Bromo-6-chloro-pyridine-2-carboxylic acid methyl ester (27.18 g, 108.5 mmol) was added to the mixture portionwise and the reaction was stirred at room temperature for 19 h. The reaction was quenched by the addition of water, and the organic layer was washed with water and saturated aqueous K2C03. The organic layer was dried (MgS04) and concentrated in vacuo to give 3-bromo-6-chloro-pyridine-2-carboxylic acid N-oxide as a yellow oil.Characterising data for the compound are as follows: NMR (400 MHz, CD3OD) delta ppm 7.77-7.75 (m, 2H) and 4.01 (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 1214328-96-7, Methyl 3-bromo-6-chloropicolinate.

Reference:
Patent; SYNGENTA LIMITED; WHITTINGHAM, William Guy; HACHISU, Shuji; ASPINALL, Mary, Bernadette; HOTSON, Matthew, Brian; WO2011/144891; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1030626-87-9 , The common heterocyclic compound, 1030626-87-9, name is 8-Bromo-5-chloro-[1,2,4]triazolo[1,5-a]pyridine, molecular formula is C6H3BrClN3, 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.5 (5-Chloro-[l, 2, 4]triazolo[l, 5-a]pyridin-8-yl)-(4-morpholin-4-yl-phenyl)-amine[0332] A suspension of 8-bromo-5-chloro-[l,2,4]triazolo[l,5-a]pyridine (160 mg, 0.69 mmol),4-morpholin-4-yl-phenylamine (135 mg, 0.76 mmol), sodium-tert-butoxide (93 mg, 0.96 mmol), tris(dibenzylideneacetone)dipalladium (0) (13 mg, 13.76 mumol) and Xantphos (16 mg, 27.52 mumol) in dry toluene is heated at 90 0C in a sealed tube under a nitrogen atmosphere for 16 hours. The reaction mixture is evaporated to dryness and the residue partitioned between dichloromethane and 10 % aqueous citric acid. The organic phase is further washed with water (Ix) and brine (Ix), dried over magnesium sulfate, filtered and evaporated. The solid residue (207 mg) is purified by flash chromatography (silica gel, dichloromethane/methanol 97:3) affording the title compound (70 mg) as a solid.

The synthetic route of 1030626-87-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GALAPAGOS N.V.; BURRITT, Andrew; WO2008/65198; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 195044-14-5, 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 195044-14-5, name is 2-Bromo-6-tert-butylpyridine. This compound has unique chemical properties. The synthetic route is as follows.

Example 58A[0972] 2-(benzylthio)-6-tert-butylpyridine[0973] To a solution of benzyl mercaptan (0.22 mL, 1.87 mmol) in anhydrous N,N- dimethylformamide (10 mL) was added a 1.0 M solution of potassium tert-butoxide in tetrahydrofuran (1.87 mL, 1.87 mmol) dropwise over 2 minutes. To the resulting suspension was added 2-bromo-6-tert-butylpyridine (0.20 g, 0.93 mmol), and the resulting mixture was stirred at 50 C for 16 hours. The cooled mixture was poured into water (50 mL) and extracted with ethyl acetate (50 mL), and the ethyl acetate layer was dried over Na2S04, filtered and concentrated in vacuo to give a crude product. Purification by column chromatography on silica gel using hexanes gave the titled compound. XH NMR (300 MHz, CDC13) delta ppm 1.35 (s, 9 H), 4.50 (s, 2 H), 6.93 – 7.03 (m, 2 H), 7.17 – 7.45 (m, 6 H); MS (APCI) m/z 258.3 (M+H)+.

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 195044-14-5, 2-Bromo-6-tert-butylpyridine.

Reference:
Patent; ABBVIE INC.; LI, Tao; PATEL, Sachin, V.; PERNER, Richard, J.; RANDOLPH, John, T.; SCHRIMPF, Michael, R.; WOLLER, Kevin, R.; XIA, Zhiren; ZHANG, Qingwei; WO2013/49174; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 20970-75-6 , The common heterocyclic compound, 20970-75-6, name is 2-Cyano-3-methylpyridine, molecular formula is C7H6N2, 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.

In a 40mL reaction bottle,Add 29.3mg (0.08mmol, 0.01eq.) In sequenceAllyl palladium chloride dimer, 92.6mg (0.16mmol, 0.02eq.)4,5-bis(diphenylphosphino)-9,9-dimethylxanthene, 10.1mL1,4-dioxane, 1.38g (8mmol, 1.0eq.)2-Bromo-3-methylpyridine, 1.69g (4mmol, 0.5eq.)Potassium ferrocyanide trihydrate and 5.1mL water, adjust and control the temperature of the reaction liquid 95-105 , stirring for 18 hours;After the reaction,Add aqueous sodium hydroxide solution [0.38g (9.6mmol, 1.2eq.)Sodium hydroxide dissolved in 5.1mL water],Adjust and control the temperature of the reaction liquid 35-45 , stirring for 3 hours,Adjust the pH to 7-8 with 6M hydrochloric acid aqueous solution, and concentrate by distillation under reduced pressure at 50 C.Get a yellow-green solid,Column chromatography (200-300 mesh silica gel) separated 1.02g of light yellow solid,The yield was 93.6%. Analysis conditions are the same as in Example 1

The synthetic route of 20970-75-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shanghai He Quan Pharmaceutical Co., Ltd.; Wang Xiaowei; Yao Lianbin; Zhu Jingyang; Fu Xiaoyong; Chen Minzhang; (6 pag.)CN110922285; (2020); A;,
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.18368-73-5, name is 3-Methyl-2-nitropyridine, molecular formula is C6H6N2O2, molecular weight is 138.12, as common compound, the synthetic route is as follows.Computed Properties of C6H6N2O2

3-(Bromomethyl)-2-nitropyridine (3); A solution of 3-methyl-2-nitropyridine (2) (12.4 g, 90.0 mmol), NBS (16.0 g, 90.4 mmol) and AIBN (0.5 g, 3.0 mmol) in 0014 (50 mL) was refluxed overnight. TLC (Eluant: 20:1 petroleum ether/EtOAc) showed that most of the starting material had been consumed. The precipitate was filtered off and the filtrate was concentrated under reduced pressure to give a residue (12.6 g), which was used in the next step without purification.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,18368-73-5, 3-Methyl-2-nitropyridine, and friends who are interested can also refer to it.

Reference:
Patent; Pfizer Inc; US2010/324043; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 84539-34-4, 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 84539-34-4 as follows.

A solution of 3,5-dibromo-4-amino-pyridine 1 (4.0 g, 15.87 mmol), Pd(PPh3)4 (0.91 g, 0.78 mmol) and aqueous solution of Na2CO3 (23.8 ml, 2M ) in toluene (80 ml ) is added to a solution of dichlorobenzene boronic acid (6.23 g, 46.4 mmole) in ethanol (24 ml). The mixture is refluxed for 14 h., diluted with ethyl acetate and washed with saturated NH4Cl solution. The organic layer is dried over sodium sulfate and concentrated in vacuo. The residue is chromatographed on silica gel to give 2.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,84539-34-4, its application will become more common.

Reference:
Patent; Bristol-Myers Squibb Company; US6352990; (2002); B1;,
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. 195044-14-5, name is 2-Bromo-6-tert-butylpyridine, molecular formula is C9H12BrN, 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 195044-14-5

Step-1: Synthesis of 1-(6-(tert-butyl)pyridin-2-yl)-2-cyclopropyl-6-(methylthio)-1,2-dihydro-3H-pyrazolo[3,4-d]pyrimidin-3-one To a stirred solution of 2-cyclopropyl-6-(methylthio)-1,2-dihydro-3H-pyrazolo[3,4-d]pyrimidin-3-one (500 mg, 2.242 mmol, 1.0 eq) and 2-bromo-6-(tert-butyl)pyridine (586 mg, 2.690 mmol, 1.20 eq) in (12 mL) of dioxane was added potassium carbonate (619 mg, 4.484 mmol, 2.0 eq) and the resulting mixture was purged with nitrogen for 10 min followed by addition of copper iodide (85 mg, 0.448 mmol, 0.2 eq), and N,N’-dimethylethylenediamine (DMEDA) (80 mg, 0.896 mmol, 0.4 eq) and again purged with nitrogen for 10 min, stirred at 90 C. for overnight. After completion of reaction, the reaction mixture was diluted with water and extracted with EtOAc (50 mL*2). The combined organic layer was washed with water (50 mL), brine solution (50 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford crude product, which was purified by flash chromatography [silica gel 100-200 mesh; elution 0-30% EtOAc in hexane] to afford the desired product, 1-(6-(tert-butyl)pyridin-2-yl)-2-cyclopropyl-6-(methylthio)-1,2-dihydro-3H-pyrazolo[3,4-d]pyrimidin-3-one (300 mg, 37.51%) as light yellow viscous.

With the rapid development of chemical substances, we look forward to future research findings about 195044-14-5.

Reference:
Patent; giraFpharma LLC; Chakravarty, Sarvajit; PHAM, Son Minh; Kankanala, Jayakanth; AGARWAL, Anil Kumar; PUJALA, Brahmam; SONI, Sanjeev; ARYA, Satish K.; PALVE, Deepak; Gupta, Ashu; KUMAR, Varun; (498 pag.)US2019/106427; (2019); 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.17282-01-8, name is 3-Bromo-2-fluoro-5-picoline, molecular formula is C6H5BrFN, molecular weight is 190.01, as common compound, the synthetic route is as follows.Formula: C6H5BrFN

Example 20i 3-Bromo-5-methylpicolinonitrile Potassium cyanide (5.76 g, 88.42 mmol) was added to a solution of 3-bromo-2-fluoro-5-methylpyridine (14 g, 73.68 mmol) in DMSO (75 mL) at rt. The resulting mixture was stirred at 110 C. for 1 h. More potassium cyanide (1.5 g, 23.03 mmol) was added and stirring continued for 20 min. Then the temperature was lowered to 80 C. and the mixture stirred over night. When cooled to rt, the mixture was poured into water (200 mL) and extracted with DCM (3*100 mL). The combined organics were washed with water (100 mL) then poured into a phase separator. The organic phase was collected, silica was added and the mixture was concentrated until a free flowing powder was obtained. The residue was purified on a silica gel column eluted with 0-50% EtOAc in heptane to afford 6.92 g (48% yield) of the title compound: 1H NMR (400 MHz, DMSO-d6) delta ppm 8.57-8.68 (m, 1H) 8.21-8.34 (m, 1H) 2.40 (s, 3 H); MS (CI) m/z 197, 199 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,17282-01-8, 3-Bromo-2-fluoro-5-picoline, and friends who are interested can also refer to it.

Reference:
Patent; ASTRAZENECA AB; US2010/125081; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 64951-08-2, Imidazo[1,2-a]pyridine-2-carboxylic 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 Imidazo[1,2-a]pyridine-2-carboxylic acid, blongs to pyridine-derivatives compound. Application In Synthesis of Imidazo[1,2-a]pyridine-2-carboxylic acid

To a solution of 23-1 (O.lg, 0.7mmol) in EtOH (15ml) in a dried flask was added Pt2O (O. Ig, 0.4mmol). The reaction mixture was placed under a nitrogen atmosphere and was subsequently evacuated. This was repeated 3 times before placing the reaction mixture under an atmosphere of hydrogen. After 3h the reaction mixture was filtered through celite. Upon solvent removal the desired product 23-2 was obtained as an off-white powder. MS calculated M+H: 167.2, found 167.1

At the same time, in my other blogs, there are other synthetic methods of this type of compound,64951-08-2, Imidazo[1,2-a]pyridine-2-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; MERCK & CO., INC.; WO2006/135627; (2006); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem