Tag: M.W=300-400

Reference of 188425-85-6, 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. 188425-85-6, name is 2-Chloro-N-(4′-chloro-[1,1′-biphenyl]-2-yl)nicotinamide. A new synthetic method of this compound is introduced below.

Add in a 100ml round bottom flask11-bromodecanoic acid 1 g (3.77 mmol),EDCI (0.72 g, 3.77 mmol) and HoBT (0.5 g, 3.77 mmol),Add 40 ml of dichloromethane to react for 15 min.Then, Boscalid {2-Chloro-N-(4′-chloro-[1,1′-biphenyl]-2-yl)nicotinamide} 1.24 g (3.6 mmol) was added. After 4 h of reaction, 1.5 g of 2-chloro-N-(4-chlorobiphenyl-2-yl)-N-(11-bromoundecyl)nicotinamide was obtained in a yield of 93%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,188425-85-6, its application will become more common.

Reference:
Patent; China Agricultural University; Tan Zhaohai; Wang Jiayao; Liu Xuelian; Tang Dachao; Xiao Yumei; Li Jiaqi; (46 pag.)CN109053801; (2018); A;,
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. 16727-47-2, name is 2,6-Bis(benzyloxy)-3-bromopyridine, the common compound, a new synthetic route is introduced below. Computed Properties of C19H16BrNO2

To a stirred solution of 2-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2- yl)benzo[d]thiazole (36-2) (1.1 g, 3.99 mmol) and 2,6-bis(benzyloxy)-3-bromopyridine 25-1 (1.9 g, 5.13 mmol) in a sealed tube, in Dioxane (20 mL ) and Water (2 mL ), was added K3PO4 (2.1 g, 9.12mmol) and the solution was degassed for 10 min. PdCl2(dppf)-DCM (0.400 g, 489 mumol) was added and again the solution was degassed for 5 min. After degassing completion, the sealed tube was closed with a teflon cap and the reaction mixture was stirred at 80c for 16 h. After reaction completion, as checked by TLC, the reaction mixture was filtered through celite. The organic layer was diluted with ethyl acetate, washed with water and brine, dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure. The crude material was purified by column chromatography eluted with 5 to 20 % ethyl acetate in hexane to provide 5- (2,6-Bis-benzyloxy-pyridin-3-yl)-2-methyl-benzothiazole (36-3) (1.0 g, 2.28 mmol, 57% yield). LC MS: ES+ 439.3.

The synthetic route of 16727-47-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; C4 THERAPEUTICS, INC.; PHILLIPS, Andrew, J.; NASVESCHUK, Chris, G.; HENDERSON, James, A.; LIANG, Yanke; HE, Minsheng; LAZARSKI, Kiel; VEITS, Gesine, Kerstin; VORA, Harit, U.; (794 pag.)WO2017/197046; (2017); 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.153747-97-8, name is tert-Butyl 4-(5-bromopyridin-2-yl)piperazine-1-carboxylate, molecular formula is C14H20BrN3O2, molecular weight is 342.23, as common compound, the synthetic route is as follows.Application In Synthesis of tert-Butyl 4-(5-bromopyridin-2-yl)piperazine-1-carboxylate

To a stirred solution of tert-butyl 4-(5-bromopyridin-2-yl)piperazine-1-carboxylate (10 g, 29.21 mmol) in 1,4-dioxane (50mL), 4N HCI solution in dioxane (100 mL, 10V) was added and the mixture was stirred 4 h at rt. The white precipitate formed was filtered and residue was washed with diethyl ether (25 mL) to afford the title compound. Yield: 95.2% (9 g, off white solid). 1H NMR (400 MHz, DMSO-d6): delta 10.05 (br s, 2H), 8.21 (d, J = 2.4 Hz, 1 H), 7.82 (dd, J = 9.2, 2.4 Hz, 1 H), 6.99 (d, J = 9.2 Hz, 1 H), 3.80-3.77 (m, 4H), 3.33-3.13 (m, 4H). LCMS: (Method A) 243.9 (M +2H), Rt. 1.69 min, 99.3 % (Max).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,153747-97-8, tert-Butyl 4-(5-bromopyridin-2-yl)piperazine-1-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; ASCENEURON S. A.; QUATTROPANI, Anna; KULKARNI, Santosh, S.; GIRI, Awadut Gajendra; (247 pag.)WO2017/144639; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 153747-97-8, 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. 153747-97-8, name is tert-Butyl 4-(5-bromopyridin-2-yl)piperazine-1-carboxylate, molecular formula is C14H20BrN3O2, 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.

Step II: tert-butyl 4-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyridyl]piperazine-1-carboxylate (Intermediate 1-XIII) A mixture of 1-11 (4.30 g, 12.57 mmol), bis(pinacolato)diboron (3.82 g, 15.07 mmol) and KOAc (2.94 g, 37.69 mmol) in 1,4-dioxane (30 mL) was degassed in a stream of argon for 15 minutes. To the mixture was added 1,1-bis(diphenylphosphino) ferrocene-palladium(II) dichloride dichloromethane complex (0.307 g, 0.376 mmol), and the reaction mixture was again degassed for additional 15 minutes. After stirring at 100 C. for 20 hours, the volatiles were removed by evaporation, and the obtained residue was diluted with water (50 mL), followed by extraction with ethyl acetate (50 mL*3). The combined organic layers were washed with brine (50 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (100-200 mesh) using 50% EtOAc in hexanes to give the desired product Intermediate 1-XIII as a mixture of minor boronate ester together with major boronic acid (4.8 g, crude yield 98%) as a yellow solid; LCMS (for boronate ester): m/z 390.2 [M+1]; LCMS (for boronic acid): m/z 308.1 [M++1].

According to the analysis of related databases, 153747-97-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; KOUL, Summon; KURHADE, Suresh; BHOSALE, Sandeep; NAIK, Keshav; SALUNKHE, Videsh; MUNOT, Yogesh; BHUNIYA, Debnath; (132 pag.)US2017/8885; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 79491-46-6 ,Some common heterocyclic compound, 79491-46-6, molecular formula is C6H4Br2N2O3, 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.

To a solution of Compound 138 (200 mg, 0.64 mmol) in anhyd MeOH (6 mL) was added NaOMe (46 mg, 0.85 mmol). The reaction mixture was stirred at room temperature for 1 h and then concentrated under vacuum. The resulting residue was washed with water and filtered. The collected solids were washed with ice cold water and dried under vacuum to give Compound 139 (150 mg, 89% yield).

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. 79491-46-6, 2,6-Dibromo-3-methoxy-5-nitropyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; EXELIXIS, INC.; BANNEN, Lynne Canne; BUI, Minna; JIANG, Faming; WANG, Yong; XU, Wei; (235 pag.)WO2019/148043; (2019); 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. 153747-97-8, name is tert-Butyl 4-(5-bromopyridin-2-yl)piperazine-1-carboxylate, molecular formula is C14H20BrN3O2, 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. Quality Control of tert-Butyl 4-(5-bromopyridin-2-yl)piperazine-1-carboxylate

A mixture of 1-28 (4.30 g, 12.57 rnmol), bis(pinacolato)diboron (3.82 g, 15.07 mmcl) and KOAc (2.94 g, 37.69 mmcl) in 1,4-dioxane (30 mL) was degassed in a stream of argon for 15 minutes. To the mixture was added 1,1- bis (diphenylphosphino) ferrocenepalladium(II) dichloridedichloromethane complex (0.307 g, 0.376 mmcl), and the reaction mixture was again degassed for additional 15 minutes. After stirring at 100C for 20 hours, the volatiles were removed by evaporation, and the obtained residue was diluted with water (50 mL), followed by extraction with ethyl acetate(50 mL x 3) . The combined organic layers were washed with brine (50 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (100-200 mesh) using 50% EtOAc in hexanes to give the desired product Intermediate 1-CII as a mixture of minor boronate ester together with major boronic acid (4.8 g, crude yield 98%) as a yellow solid; IJCMS (for boronate ester): m/z 390.2 [M+1]; LCMS (for boronic acid): m/z 308.1 [M+1].

With the rapid development of chemical substances, we look forward to future research findings about 153747-97-8.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; KOUL, Summon; KURHADE, Suresh; NAIK, Keshav; SALUNKHE, Videsh; KULKARNI, Rakesh; PARDESHI, Vishwajeet; BHUNIYA, Debnath; KULKARNI, Bheemashankar; MOOKHTIAR, Kasim Abbaas; (274 pag.)WO2017/38909; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 153747-97-8, 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 153747-97-8, name is tert-Butyl 4-(5-bromopyridin-2-yl)piperazine-1-carboxylate. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of tert -butyl 4-(5-bromopyridin-2-yl)piperazine-l-carboxylate (250 mg, 0.730 mmol) in 2.5 mL anhydrous THF was added 2.5 M w-butyllithium (320 muL, 0.80 mmol) at -78 0C under nitrogen atmosphere. After stirring for 45 mins, the reaction mixture was charged with dimethyl phosphinic chloride (164.4 mg, 1.46 mmol) in 1 mL anhydrous THF. The reaction mixture was warmed to -30 0C over 3 h. The mixture was quenched with saturated ammonium chloride aqueous solution and the mixture was partitioned between DCM and brine. The organic layer was dried over Na2SO4 and concentrated to afford the crude material. The resulting solid was purified by flash chromatography on silica gel, eluting with 20 – 100% EtOAc : heptane. Fractions containing the desired product were combined and concentrated to afford an off white solid (100 mg, 40.3% yield). The Boc protected title compound was dissolved in 2-PrOH (1 mL) and charged with 4 N HCl. The reaction mixture was heated at 70 0C for 30 min, and concentrated to afford the titled product as a HCl salt. MS (m/z, MH+): meas. 240.2 calc. 240.3

According to the analysis of related databases, 153747-97-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NOVARTIS AG; WO2008/110611; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 59020-10-9 ,Some common heterocyclic compound, 59020-10-9, molecular formula is C17H31NSn, 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.

147a. 6-Chloro-3-(1-methyl-2-(S)-pyrrolidinylmethoxy)-5-(3-pyridyl)pyridine To a solution of 3-(1-methyl-2-(S)-pyrrolidinylmethoxy)-5-bromo-6-chloropyridine (500 mg, 1.28 mmol) in toluene (10 mL) was added 3-pyridinyltributyltin (564 mg, 1.54 mmol) and tetrakis(triphenylphosphine)palladium(0) (45 mg, 0.04 mmol). After being heated under reflux for 16 h, the resulting mixture was cooled to room temperature. Solvent was removed, and the residue was chromatographed (silica gel; EtOAc/hexane, 2:19 to 1:1) to afford an oil (428 mg, 86%): 1H NMR (CDCl3, 300 MHz) delta 1.45 (s, 9H), 1.94 (m, 1H), 1.98-2.10 (m, 2H), 3.31-3.45 (m, 2H), 3.88-4.30 (m, 4H), 7.22 (m, 1H), 7.40 (m, 1H), 7.83 (td, 1H, J=1.5, 9.0 Hz), 8.16 (d, 1H, J=3.0 Hz), 8.64-8.73 (m, 2H); MS (CI/NH3) m/z 390 (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. 59020-10-9, 3-(Tributylstannyl)pyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Abbott Laboratories; US6437138; (2002); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 138647-49-1, 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. 138647-49-1, name is tert-Butyl 4-(((trifluoromethyl)sulfonyl)oxy)-5,6-dihydropyridine-1(2H)-carboxylate. A new synthetic method of this compound is introduced below.

To a mixture of tert-butyl4-(((trifluoromethyl)sulfonyl)oxy)-3 ,6-dihydropyridine-1(2H)-carboxylate (5.6 g, 16.8 mmol), Et3N (4.7 ml, 33.0 mmol) in DMF (69 ml) andMeOH (52 ml) was added PPh3 (0.2 g, 1.0 mmol) and Pd(OAc)2 (0.1 g, 0.5 mmol) at RT under nitrogen followed by stirring under CO atmosphere for 12 h. The reaction mixture was concentrated under reduced pressure. The crude residue was purified by column chromatography to give 2.0 g of the title compound as a greenish liquid. 1H-NMR (400MHz; DMSO-d6): oe 6.85 (d, 1H), 4.00 (t, 2H), 3.67 (s, 3H), 3.42 (d, 2H), 2.25 (t, 2H),1.41 (s, 9H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,138647-49-1, tert-Butyl 4-(((trifluoromethyl)sulfonyl)oxy)-5,6-dihydropyridine-1(2H)-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; ORION CORPORATION; DIN BELLE, David; MAeKELAe, Mikko; PASSINIEMI, Mikko; PIETIKAeINEN, Pekka; RUMMAKKO, Petteri; TIAINEN, Eija; VAISMAA, Matti; WOHLFAHRT, Gerd; (254 pag.)WO2018/115591; (2018); 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. 193274-02-1, name is tert-Butyl 3a-benzyl-2-methyl-3-oxo-3a,4,6,7-tetrahydro-2H-pyrazolo[4,3-c]pyridine-5(3H)-carboxylate. This compound has unique chemical properties. The synthetic route is as follows. Application In Synthesis of tert-Butyl 3a-benzyl-2-methyl-3-oxo-3a,4,6,7-tetrahydro-2H-pyrazolo[4,3-c]pyridine-5(3H)-carboxylate

A clean, nitrogen purged reactor was charged with methylene chloride (471 L) and 2,3,3a,4,6,7-hexahydro-2-methyl-3-oxo-3a-(phenylmethyl)-5H-pyrazolo[4,3-c]pyridine-5-carboxylic acid 1,1-dimethylethyl ester (prepared according to Preparation Five, Step E, 47.0 kg, 1.0 eq.). The mixture was agitated and cooled to between -5C and 5C. The reaction mixture was slowly charged with triflouroacetic acid (117 kg, 7.5 eq.). The reaction mixture was warmed to a temperature between 20C and 30C and stirred for 12 to 15 hours. The reaction mixture was quenched by slow addition of an aqueous solution of 10% sodium carbonate (486 L, 0.5 eq.) at a temperature between 5C and 15C. The organic layer was separated and the aqueous layer extracted with methylene chloride (19 L). A mixture of acetone (456 L), water (56.4 L), and L-tartaric acid (22.6 kg, 1.1 eq.) was prepared in a second reactor. The tartaric acid mixture was combined with the organic layers at a temperature between 20C and 25C. The resulting slurry was heated to a temperature between 35C and 45C and stirred for 8 to 18 hours (overnight). When the reaction was judged to be complete, the slurry was cooled and granulated at a temperature between 0C and 10C for three to four hours and filtered. The product cake was washed with a mixture of acetone (40 L) and water (4.5 L). The product was dried under vacuum using only mild heat (applied if evaporation of acetone results in cooling). A yield of 37.7 kg of (3aR)-2,3a,4,5,6,7-hexahydro-2-methyl-3a-(phenylmethyl)-3H-pyrazolo[4,3-c]pyridin-3-one, (2R,3R)-2,3-dihydroxybutanedioate (1:1) was obtained (70.1% yield).

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, 193274-02-1, tert-Butyl 3a-benzyl-2-methyl-3-oxo-3a,4,6,7-tetrahydro-2H-pyrazolo[4,3-c]pyridine-5(3H)-carboxylate.

Reference:
Patent; Pfizer Products Inc.; EP1031575; (2000); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem