Tag: M.W:100-200

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. 115473-15-9, name is 5,6,7,7a-Tetrahydrothieno[3,2-c]pyridin-2(4H)-one hydrochloride, molecular formula is C7H10ClNOS, 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: 5,6,7,7a-Tetrahydrothieno[3,2-c]pyridin-2(4H)-one hydrochloride

Method AIn a 2 ltr 4-necked flask equipped with a thermometer and mechanical stirrer, Tert.- butyldimethylsilylchloride (90 g, 0.60 moles) was added slowly in a mixture of 5,6,7,7a-Tetrahydro-4H-thieno-[3,2-c]- pyridone-2 hydrochloride (100 g, 0.52 moles) and triethyl amine (56 g 0.55 moles) in dichloromethane (300 ml) at 0 +/-5 C under nitrogen atmosphere. Stir the reaction mass for 4 to 6 hrs at 20 +/-5 C. Slowly add 2- Fluoro-a-cyclopropyl carbonylbenzyl bromide (148 g, 0.58 moles) and triethyl amine (101 g, 1.0 moles) and stir the reaction mass for 20 to 24 hrs. Reaction mass quench into water and product extract with dichloromethane. Organic layer wash with 10% sodium chloride solution then water. Organic layer dried over sodium sulafate and recover the solvent under vacuum. Product crystallized in methanol. Filter the product and slurry washed methanol, and Dry the material under vacuum at 40-45 C to obtain 2-(tert-Butyldimethylsilyloxy)-5-(a-cyclopropylcarbonyl-2-fluorobenzyl)-4,5,6,7- tetrahydrothieno[3,2-c]-pyridine (140 g, 99.5%).

With the rapid development of chemical substances, we look forward to future research findings about 115473-15-9.

Reference:
Patent; MAYUKA LABS PVT. LTD.; KRISHNAMURTHY, Chandra, Sekhar, Nakka; SINGH, Jagat; KHAN, Mohd, Yunus; WO2012/1486; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1122-70-9, 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. 1122-70-9, name is 6-Methyl-2-vinylpyridine. A new synthetic method of this compound is introduced below.

Step F: Preparation of 1-[2-(6-Methyl-2-pyridyl)ethyl]-4-(benzofurazan-5-carbonyl)piperidine dihydrochloride 4-(Benzofurazan-5-carbonyl)piperidine hydrochloride (268 mg, 1 mmol), 2-methyl-6-vinylpyridine (286 mg, 2.4 mmol) and sodium acetate (187 mg, 2.3 mmol) in methanol/water (1:1, 4 ml) were heated under reflux for 3 hours, cooled and the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography on silica gel, eluding with CH2 Cl2 /CH3 OH/NH3 (Aq.); 96:4:0.4 to give a light brown solid. This was suspended in ethanol (2 ml) and ethanolic HCl (Ca. 1M, 2 ml) was added. The mixture was stirred at room temperature for 4 hours and the solid was collected and dried in vacuo to give the dihydrochloride as a light brown solid (260 mg. 61%), mp 228-231 C. deltaH(DMSO) 11.1 (1H, br s), 9.05 (1H, s), 8.25 (1H, br m), 8.19 (1H, d, J 9.5 Hz), 7.99 (1H, d, J 9.5 Hz), 7.65 (2H, br m), 4.0-3.1 (10H, m), 2.71 (3H, s), and 2.10 (4H, br m). Elemental analysis for C20 H22 N4 O2.2HCl: Calculated: C, 56.74; H, 5.71; N, 13.23%. Found: C, 56.34; H, 5.80; N, 13.13%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1122-70-9, its application will become more common.

Reference:
Patent; Merck & Co., Inc.; US5112824; (1992); 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.73895-98-4, name is 6-Bromo-4-methylpyridin-2-amine, molecular formula is C6H7BrN2, molecular weight is 187.04, as common compound, the synthetic route is as follows.SDS of cas: 73895-98-4

This compound was forwarded to the next step without further purification. To a stirred solution of 6-amino-2-bromo-4-methylpyridine (45.2 g; 0.24 mol) in 100 ml water and 43 g concentrated sulphuric acid at ice-bath temperature was given a solution of sodium nitrite (13.2 g; 0.19 mol) in 20 ml water. After 2 hours the reaction mixture was warmed to 60 C. and stirred for further 60 minutes. After cooling, the mixture was extracted with 200 ml of dichloromethane. The solvent was removed in vacuo and 2-bromo-4-methyl-6-hydroxypyridine (20 g, 56%) was obtained as colourless crystals of melting point 152 C.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,73895-98-4, 6-Bromo-4-methylpyridin-2-amine, and friends who are interested can also refer to it.

Reference:
Patent; American Cyanamid Company; US5840654; (1998); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1122-54-9, 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.1122-54-9, name is 4-Acetylpyridine, molecular formula is C7H7NO, molecular weight is 121.14, as common compound, the synthetic route is as follows.

To a mixture of NaH (6.6 g, 165.2 mmol, 60%in mineral oil) in toluene (120 mL) was added dimethyl carbonate (11.2 g, 123.9 mmol) in toluene (40 mL) . Then 1- (pyridin-4-yl) ethanone (5.0 g, 41.3 mmol, 5) in toluene (40 mL) was added dropwise under N 2. The reaction mixture was stirred at 105 for 12 hours. After cooled to RT, the reaction was quenched with 200 mL (water) and HOAc (20 mL) and the mixture was stirred at RT for 20 minutes. Then the mixture was extracted with EtOAc (300 mL*3) . The combined organic layer was dried over Na 2SO 4, filtered and concentrated. The residue was purified by Prep-HPLC (water/acetonitrile = 10%to 90%) to give the title product (3.89 g, 53%, 6) as a brown solid. LC-MS: Rt = 1.20 min, [M+H] + = 180.

The chemical industry reduces the impact on the environment during synthesis 1122-54-9, I believe this compound will play a more active role in future production and life.

Reference:
Patent; SHANGHAI CHANGCHENGYIYAOKEJI COMPANY LIMITED; XU, Mingyan; (0 pag.)WO2020/1475; (2020); 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. 1215387-58-8, name is 5-Bromo-1H-pyrrolo[2,3-c]pyridine. A new synthetic method of this compound is introduced below., Application In Synthesis of 5-Bromo-1H-pyrrolo[2,3-c]pyridine

A stirred solution of 5-bromo-1H-pyrrolo[2,3-c]pyridine (2.22 g, 11.3 mmol) in DMF(30 ml) at ambient temperature was treated with potassium hydroxide (2.53 g, 45.1mmol). After 10 minutes, iodine (3.15 g, 12.4 mmol) was added and the resulting mixture was stirred for 2 hours. The mixture was diluted with water and extracted with EtOAc. The combined organic extracts were washed with brine, dried over Na2SO4 and concentrated in vacuo. The residue was triturated with water to afford the desiredproduct as an orange solid (3.39 g, 93%).LCMS (Method C): R 3.14 mm, mlz [M+H] 323/325.

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, 1215387-58-8, 5-Bromo-1H-pyrrolo[2,3-c]pyridine.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; HYND, George; TISSELLI, Patrizia; MACLEOD, Calum; MANN, Samuel, Edward; PANCHAL, Terry, Aaron; MONTANA, John, Gary; PRICE, Stephen, Colin; (74 pag.)WO2016/62790; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 13466-38-1, 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. 13466-38-1, name is 5-Bromopyridin-2-ol, molecular formula is C5H4BrNO, 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.

termediate 17 ethyl trans-4-[(“5-bromopyridin-2-yl oxylcvclohexanecarboxylate To a mixture of 5-bromo-2-hydroxypyridine (11 g, 63.2 mmol), ethyl cis-4- hydroxycyclohexanecarboxylate (13.61 g, 79 mmol) and triphenylphosphine (20.73 g, 79 mmol) in THF (250 ml) at room temperature added diisopropyl azodicarboxylate (15.98 g, 79 mmol) dropwise, after that, the reaction mixture Was stirred overnight a at 55C for two days under N2. The reaction mixture was cooled to room temperature, then concentrated under vacuum. The residue was dissolved in 100 mL of ethyl acetate, then 100 mL hexane added. Stirred over night. The mixture was filtered and concentrated, the residue was purified by a silica gel column and eluted with ethyl acetate/hexane 0-50%. This resulted in ethyl trans-4- [(5-bromopyridin-2-yl)oxy]cyclohexanecarboxylate as a white solid. LC-MS (ES, m/z) C14H18BrN03: 327; Found: 328 [M+H]+.

According to the analysis of related databases, 13466-38-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME CORP.; DEVITA, Robert, J.; HE, Shuwen; LIU, Jian; CERNAK, Timothy, A.; KRIKORIAN, Arto, D.; YANG, Ginger XuQiang; WU, Zhicai; YU, Yang; SHEN, Dong-Ming; LAI, Zhong; HONG, Qingmei; NARGUND, Ravi, P.; WO2013/96093; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 13362-78-2, (E)-1,2-Di(pyridin-4-yl)ethene, 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, 13362-78-2, blongs to pyridine-derivatives compound. HPLC of Formula: C12H10N2

A mixture of (E)-1,2-di(4-pyridyl)ethylene (91 mg, 0.5 mmol) and 1,4-butanesultone (204 mg, 1.5 mmol) (Aldrich) was heated at 140 °C (oil bath) for 40 h. The resulting mass was refluxed with benzene (~15 mL) for 2 h, filtered, washed with benzene and acetone, and re-crystallized from water-EtOH (2.5:1 (v/v), 1.4 mL) to yield 184 mg (81percent) (E)-3c as a white powder.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,13362-78-2, its application will become more common.

Reference:
Article; Vedernikov, Artem I.; Lobova, Natalia A.; Kuz’mina, Lyudmila G.; Howard, Judith A.K.; Strelenko, Yuri A.; Alfimov, Michael V.; Gromov, Sergey P.; Journal of Molecular Structure; vol. 989; 1-3; (2011); p. 114 – 121;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 14294-11-2 ,Some common heterocyclic compound, 14294-11-2, molecular formula is C6H7N3S, 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.

Analogously to Example 1, but using pyridyl-thiourea in place of 2-imino-4-thiobiuret, there is obtained ethyl 2-(pyridin-2-ylamino)-thiazole-4-carboxylate; MS: 250 (M+H)+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,14294-11-2, its application will become more common.

Reference:
Patent; Hoffman-La Roche Inc.; US6100282; (2000); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 3430-17-9, 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 3430-17-9, name is 2-Bromo-3-methylpyridine. This compound has unique chemical properties. The synthetic route is as follows.

[00299] 2-Bromo-3-methylpyridine (1.0 eq) was dissolved in toluene (12 vol). K2C03 ( 4.8 eq)was added, followed by water (3.5 vol). The resulting mixture was heated to 65 oc under astream ofN2 for 1 hour. 3-(t-Butoxycarbonyl)phenylboronic acid (1.05 eq) andPd(dppf)Cb·CH2Cb (0.015 eq) were then added and the mixture was heated to 80 C. After 2hours, the heat was turned off, water was added (3.5 vol), and the layers were allowed toseparate. The organic phase was then washed with water (3.5 vol) and extracted with 10%aqueous methanesulfonic acid (2 eq MsOH, 7.7 vol). The aqueous phase was made basic with50% aqueous NaOH (2 eq) and extracted with EtOAc (8 vol). The organic layer wasconcentrated to afford crude tert-butyl-3-(3-methylpyridin-2-yl)benzoate (82%) that was useddirectly in the next step.

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 3430-17-9, 2-Bromo-3-methylpyridine.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; VERWIJS, Marinus, Jacobus; KARKARE, Radhika; MOORE, Michael, Douglas; WO2014/71122; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 897732-75-1, Adding some certain compound to certain chemical reactions, such as: 897732-75-1, name is 2-Methyl-6-(methylsulfonyl)pyridin-3-amine,molecular formula is C7H10N2O2S, 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 897732-75-1.

Step 1: Acetic acid 6-methanesulfonyl-2-methyl-pyridin-3-yl ester; A solution of boron trifluoride etherate (670 muL, 5.3 mmol) in dimethylformamide (2 mL) was cooled to -15 C. using an ice-acetonitrile bath, and then stirred for 15 min at this temperature. A solution of 6-methanesulfonyl-2-methyl-pyridin-3-ylamine (Intermediate 4; 653 mg, 3.5 mmol) in 1,2-dimethoxyethane (16 mL) was added dropwise to the solution at -15 C. and the stirring was continued for a further 15 min. tert-Butyl nitrite (Aldrich Chemical Company, Inc., Milwaukee, Wis., USA 90%; 483 mg, 4.2 mmol) was added dropwise, and the reaction mixture was stirred at -15 C. for 15 min and then at 0 C. for 1 h. Hexane (20 mL) was added and the solid was filtered off and washed with hexane. The solid was added to acetic anhydride (5 g, 49 mmol) and the mixture was heated at 100 C. for 1 h. The acetic anhydride was evaporated under high vacuum and then 1 M aqueous sodium carbonate solution was added. The mixture was extracted three times with dichloromethane. The dichloromethane was evaporated and the residue was purified by silica gel column chromatography, eluting with 0-40% ethyl acetate/hexane to give acetic acid 6-methanesulfonyl-2-methyl-pyridin-3-yl ester (331 mg, 41%) as a solid. 1H NMR (CDCl3) delta 2.39 (s, 3H), 2.52 (s, 3H), 3.22 (s, 3H), 7.62 (d, 1H, J=8.2 Hz), 7.98 (d, 1H, J=8.4 Hz).

According to the analysis of related databases, 897732-75-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Erickson, Shawn David; Gillespie, Paul; Guertin, Kevin Richard; Karnachi, Prabha Saba; Kim, Kyungjin; Ma, Chun; McComas, Warren William; Pietranico-Cole, Sherrie Lynn; Qi, Lida; Tilley, Jefferson Wright; Zhang, Qiang; US2009/286812; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem