Tag: M.W:200-300

Electric Literature of 1206775-52-1 ,Some common heterocyclic compound, 1206775-52-1, molecular formula is C7H6BrNO2, 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.

(2) Tetrakistriphenylphosphine palladium (403 mg), phenylboronic acid (510 mg) and a 2 M sodium carbonate solution (3.5 mL) were sequentially added to a solution of 5-bromo-6-methoxypyridine-2-carbaldehyde (753 mg) in 1,2-dimethoxyethane (23 mL) in a nitrogen atmosphere, and the mixture was stirred at 80 C. for three hours. Water was added to the reaction solution at room temperature, followed by extraction with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate and filtered. The solvent was then evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=50:1?1:1) and further purified by silica gel column chromatography (hexane:ethyl acetate=50:1) to give 6-methoxy-5-phenylpyridine-2-carbaldehyde (445 mg, 60%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1206775-52-1, its application will become more common.

Reference:
Patent; TAISHO PHARMACEUTICAL CO., LTD; NISSAN CHEMICAL INDUSTRIES, LTD.; US2011/237791; (2011); 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.185017-72-5, name is 3-Bromo-2-chloro-6-picoline, molecular formula is C6H5BrClN, molecular weight is 206.4676, as common compound, the synthetic route is as follows.name: 3-Bromo-2-chloro-6-picoline

In 21 mL of carbon tetrachloride, 3-bromo-2-chloro-6-methylpyridine (880 mg, 4.26 mmol) was dissolved, and N-bromosuccinimide (682 mg, 3.83 mmol) and AIBN (70 mg, 0.426 mmol) were added, followed by stirring at 90C for one hour. The resulting reaction solution was concentrated, and the residue thus obtained was purified by silica gel column chromatography (chloroform/methanol = 100/0 to 95/5), whereby 3-bromo-6-(bromomethyl)-2-chloropyridine was obtained as a crude purified product.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,185017-72-5, 3-Bromo-2-chloro-6-picoline, and friends who are interested can also refer to it.

Reference:
Patent; Taiho Pharmaceutical Co., Ltd.; SUGIMOTO, Tetsuya; TAKAHASHI, Hidekazu; MITSUYA, Morihiro; MASUKO, Norio; SOOTOME, Hiroshi; EP2821406; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 106047-28-3, 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 106047-28-3 as follows.

Step 2 1-methyl-4-nitro-2-[2-(3-pyridyl)pyridin-6-ylamino]benzene This compound was prepared by version of the method described in the document (J. Org. Chem., 2000, 65, 1144-1157.). To 940 mg of 2-bromo-6-(3-pyridyl)pyridine obtained in the step 1, 730 mg of 2-methyl-5-nitroaniline, 37 mg of tris(dibenzylideneacetone)dipalladium (0), 75 mg of (+-)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl [(+-)-BINAP] and 1.82 mg of cesium carbonate, 12 ml of toluene was added and the mixture was stirred with heating at 110C for 24 hours under an argon atmosphere. After air cooling, the reaction solution was diluted with ethyl acetate and insolubles were removed by filtration. The solvent in the filtrate was distilled off under reduced pressure and the residue was crystallized by adding diethyl ether. The resulting crystal was collected by filtration and then washed with ethyl acetate-diethyl ether to obtain 646 mg of the objective compound as a yellow crystal. Melting point: 148-150C 1H-NMR(CDCl3)delta: 2.42(3H, s), 6.53(1H, br), 6.80(1H, d), 7.35(2H, d), 7.44(1H, dd), 7.69(1H, m), 7.83(1H, dd), 8.44(1H, dt), 8.65(1H, dd), 9.09(1H, d), 9.20(1H, d)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,106047-28-3, its application will become more common.

Reference:
Patent; Nippon Shinyaku Co., Ltd.; EP1533304; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1083057-12-8, tert-Butyl 3-(3-methylpyridin-2-yl)benzoate, 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 tert-Butyl 3-(3-methylpyridin-2-yl)benzoate, blongs to pyridine-derivatives compound. Safety of tert-Butyl 3-(3-methylpyridin-2-yl)benzoate

[00316] fer -Butyl-3-(3-methylpyridin-2-yl)benzoate (1.0 eq) was dissolved in EtOAc (6 vol). Water (0. 3 vol) was added, followed by urea-hydrogen peroxide (3 eq). Phthalic anhydride (3 eq) was then added portionwise to the mixture as a solid at a rate to maintain the temperature in the reactor below 45 C. After completion of the phthalic anhydride addition, the mixture was heated to 45 C. After stirring for an additional 4 hours, the heat was turned off. 10% w/w aqueous Na2S03 (1.5 eq) was added via addition funnel. After completion of Na2S03 addition, the mixture was stirred for an additional 30 min and the layers separated. The organic layer was stirred and 10% wt/wt aqueous. Na2C03 (2 eq) was added. After stirring for 30 minutes, the layers were allowed to separate. The organic phase was washed 13% w/v aq NaCl. The organic phase was then filtered and concentrated to afford crude 2-(3-(tert-butoxycarbonyl)phenyl)-3- methylpyridine-1 -oxide (95%) that was used directly in the next step.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1083057-12-8, tert-Butyl 3-(3-methylpyridin-2-yl)benzoate, and friends who are interested can also refer to it.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; SWINNEY, Kelly, Ann; HURTER, Patricia, Nell; NADIG, David, E.; SMITH, David; THOMAS, Vance, Hayden; WARMAN, Martin, Paul; WO2015/73231; (2015); 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. 77199-09-8, name is Ethyl 5-bromopicolinate, molecular formula is C8H8BrNO2, 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. Formula: C8H8BrNO2

Under the protection of N2, m-chloroperoxybenzoic acid (36.00g, 0.208 mol) was added to an ethyl acetate (126 mL) solution of ethyl 5-bromopyridine-2-carboxylate (15.00g, 0.065 mol), and the resulting mixture was heated to 70C to react overnight. After cooling, water was added. The resulting mixture was extracted with ethyl acetate, washed with a saturated sodium sulfite aqueous solution, washed with a saturated sodium carbonate aqueous solution, dried with anhydrous sodium sulfate, and concentrated. The residue was separated through a silica gel column (ethyl acetate:petroleum ether=1:5) to obtain a yellow product (6.60 g, 41%). 1H NMR (400 MHz, CDCl3,) delta 8.42 (d, 1H), 7.53 (d, 1H), 7.41-7.43 (m, 1H), 4.44-4.50 (q, 2H), 1.42 (t, 3H).

With the rapid development of chemical substances, we look forward to future research findings about 77199-09-8.

Reference:
Patent; Chia Tai Tianqing Pharmaceutical Group Co.,Ltd; Centaurus BioPharma Co., Ltd.; Lianyungang Runzhong Pharmaceutical Co., Ltd.; LI, Jijun; WU, Wei; ZHU, Yan; WANG, Huting; ZHAO, Lijia; HE, Weinan; SUN, Yinghui; PENG, Yong; HAN, Yongxin; (108 pag.)EP3412669; (2018); A1;,
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. 192447-58-8, name is 2,6-Dibromo-N,N-dimethylpyridin-4-amine. A new synthetic method of this compound is introduced below., COA of Formula: C7H8Br2N2

(3) Production of 2-bromo-4-dimethylamino-6-{3-(trifluoromethyl)phenoxy} pyridine as an intermediate product 1.4 g (0.0071*1.2 mol) of 3-(trifluoromethyl) phenol was dissolved in about 20 ml of dimethyl formamide. The solution was further mixed with 0.30 g (ca. 60% in mineral oil; 0.0071*1.06 mol) of sodium hydride and then with 2.00 g (0.0071 mol) of 2,6-dibromo-4-dimethylamino pyridine. After treating the solution under reflux for about 6 hours, the solution was allowed to stand for cooling to room temperature. After the reaction solution was distributed with hexane-saturated sodium bicarbonate water, the organic phase of the obtained solution was washed with saturated brine and dried with anhydrous sodium sulfate, followed by concentration thereof. Thereafter, the concentrated solution was purified by silica gel column chromatography (eluding solution: ethyl acetate/hexane) and the obtained product was subjected to recrystallization using hexane, thereby obtaining an aimed product. Yield by weight: 1.67 g; yield by percentage: 65%; solid; melting point: 61 to 66 C.; 1 H-NMR (60 MHz, CDCl3, delta): 2.86 (6H, s), 6.88 (1H, d, J=2 Hz), 6.38 (1H, d, J=2 Hz), 6.9-7.5 (4H, complex).

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, 192447-58-8, 2,6-Dibromo-N,N-dimethylpyridin-4-amine.

Reference:
Patent; Kureha Kagaku Kogyo Kabushiki Kaisha; US6005112; (1999); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1190319-62-0, 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.1190319-62-0, name is 6-Bromo-1H-pyrrolo[3,2-b]pyridin-2(3H)-one, molecular formula is C7H5BrN2O, molecular weight is 213.03, as common compound, the synthetic route is as follows.

Pottasium tert-butoxide (0.03 g, 0.27 mmol) was added to a suspension of 6-bromo-1H-pyrrolo[3,2-b]pyridin-2(3H)-one (preparation 16c, 0.87 g, 4.1 mmol) in dimethylsulphoxide (4 mL) and, after stirring for 10 minutes at room temperature, the mixture was heated to 40-45 C and methyl acrylate (1.14 mL, 12.71 mmol) was added dropwise over 60 minutes. After the addition, the mixture was stirred for 2 hours and then further potassium tert-butoxide (1.4 g, 12.21 mmol) was added portionwise over 30 minutes keeping the temperature below 50 C. The mixture was then heated to 100 C and stirred for 2 hours. Water (20 mL) was added and heating was continued at 85 C for 2 hours and then the mixture was left to cool overnight. Ethyl acetate was added and the organic layer was washed with water, brine, dried (MgSO4) and evaporated to give the title compound (0.60 g, 50%) as a white solid. LRMS (m/z): 293/295 (M-1)+. 1H-NMR delta (CDCl3): 2.14 (m, 2H), 2.27 (m, 2H), 2.73 (m, 2H), 3.01 (m, 2H), 7.40 (d, J=1.5 Hz, 1H), 8.29 (d, J=1.5 Hz, 1H), 8.44 (br s, 1H).

The chemical industry reduces the impact on the environment during synthesis 1190319-62-0, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Laboratorios Almirall, S.A.; EP2113503; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 86847-84-9, N-(6-Chloropyridin-2-yl)pivalamide, 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, SDS of cas: 86847-84-9, blongs to pyridine-derivatives compound. SDS of cas: 86847-84-9

Intermediate 6:[0121] A solution of intermediate 5 (19.28 g, 90.6 mmol) in THF (181 mL) was treated with 77-BuLi (108.8 mL, 272 mmol) and the resulting mixture was stirred at -20C for 3 h. After addition of DMF (20.81 mL, 271.86 mmol), the reaction was allowed to warm to rt. The reaction was poured into cold 6N HC1 and stirred for 15 min. The mixture was then neutralized with anhydrous K2C03 to pH=7 and extracted with Et20. The combined organic layers were washed with water, brine, dried over anhydrous Na2SC>4, concentrated in vacuo and purified by recrystallization from EtOAc and hexanes to afford N-(6-chloro-3-formylpyridin-2-yl)pivalamide (intermediate 6) (12.84 g, 59%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,86847-84-9, N-(6-Chloropyridin-2-yl)pivalamide, and friends who are interested can also refer to it.

Reference:
Patent; THE UNIVERSITY OF NORTH CAROLINA AT CHAPEL HILL; JIN, Jian; ROTH, Bryan; FRYE, Stephen; WO2012/3418; (2012); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 727356-19-6 ,Some common heterocyclic compound, 727356-19-6, molecular formula is C6H5BrClN, 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): 2-Bromo-6-(2,2-dipyridin-2-yl)propyl)pyridine 40 ml (100 mmol) of n-butyllithium (2.5 M in hexane) are added dropwise to a solution, cooled to -78 C., of 18.4 g (100 mmol) of 2,2′-ethylidenebis-pyridine [29280-41-9] in 500 ml of THF, and the mixture is stirred for a further 30 min. A solution of 20.6 g (100 mmol) of 2-bromo-6-chloromethylpyridine [727356-19-6] in 100 ml of THF is then added dropwise, and the mixture is then stirred at -78 C. for a further 15 min. After warming to room temperature, the solvent is removed in vacuo, the residue is taken up in 300 ml of dichloromethane, and the organic phase is washed twice with 100 ml of water each time and dried over magnesium sulfate. The residue is recrystallised twice from ethyl acetate/heptane. Yield: 19.5 g (55 mmol), 55%, 95.0% pure according to 1H-NMR.

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. 727356-19-6, 2-Bromo-6-(chloromethyl)pyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK PATENT GMBH; US2012/286254; (2012); 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 1159812-31-3, name is 7-Bromo-2-methyl-[1,2,4]triazolo[1,5-a]pyridine. This compound has unique chemical properties. The synthetic route is as follows. SDS of cas: 1159812-31-3

To 7-bromo-2-methyl-[1,2,4]triazolo[1,5-a]pyridine (2.14 g, 10.09 mmolAnd benzophenone imine (2.75g, 15.17mmol)In a solution of 1,4-dioxane (40 mL),Add Pd2(dba)3 (467.0 mg, 0.51 mmol),BINAP (95%, 664.4 mg, 1.01 mmol)And t-BuONa (1.94 g, 20.19 mmol).The reaction system was stirred at 100 C overnight.It was then cooled to room temperature and concentrated under reduced pressure.The residue obtained was purified by silica gel column chromatography (MeOH / DCThe title compound was obtained as a yellow solid (2.56 g, yield: 81.2%).

With the rapid development of chemical substances, we look forward to future research findings about 1159812-31-3.

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Jiatuo Sciences Corporation; Xi Ning; Li Minxiong; Peng Ju; Li Xiaobo; Zhang Tao; Hu Haiyang; Chen Wuhong; Bai Changlin; Ke Donghua; Chen Peng; (217 pag.)CN109776522; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem