Day: March 10, 2021

Electric Literature of 879668-17-4, 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. 879668-17-4, name is 4,5,6,7-Tetrahydro-3H-imidazo[4,5-c]pyridine hydrochloride, molecular formula is C6H10ClN3, 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 209.1 : To a suspension of 4,5,6,7-tetrahydro-3H-imidazo[4,5-c]pyridine hydrochloride (700mg) was added DIPEA (2.5ml) and Boc2O (0.945ml) at 0C. The reaction mixture was stirred at 0C for 2h, diluted with DCM and washed with water. The aq. phase was extracted with DCM. The combined org. layers were dried (MgSO4), filtered off and evaporated to dryness. The residue was purified by CC (Biotage, SNAP 25g cartridge, solvent A: DCM; solvent B: DCM/MeOH 8/2; gradient in %B: 15 for 3CV, 15 to 25 over 3CV, 25 for 5CV) to afford 1,4,6,7-tetrahydro-imidazo[4,5-c]pyridine-5-carboxylic acid tert-butyl ester (298mg, white solid). LC-MS (B): tR = 0.50min; [M+H]+: 223.96.

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 879668-17-4, 4,5,6,7-Tetrahydro-3H-imidazo[4,5-c]pyridine hydrochloride.

Reference:
Patent; ACTELION PHARMACEUTICALS LTD; CAROFF, Eva; KELLER, Marcel; KIMMERLIN, Thierry; MEYER, Emmanuel; WO2013/114332; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 148493-37-2 ,Some common heterocyclic compound, 148493-37-2, molecular formula is C5H2Cl2IN, 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 degassed solution of iodide (2.0 g, 7.30 mmol), boronic ester (2.70 mL, 7.305 mmol) and 1,1′-bis(di-tert-butylphosphino)ferrocene palladium dichloride (238 mg, 0.365 mmol)was added degassed aq. K3P04 (22 mL, 22.0 mmol, 1M). The reaction mixture was stirred atroom temperature for 16 h. The mixture was concentrated, diluted with EtOAc and the aqueouslayer was cut. The organic layer was dried over Mg2S04 and concentrated to a black oil. Themixture was purified on silica with DCM to obtain (E)-3-(4-((tert-butyldimethylsilyl)oxy)but-1-10 en-1-yl)-2,6-dichloropyridine (2.5 g, 100% yield). MS (M+Ht: 331.

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. 148493-37-2, 2,6-Dichloro-3-iodopyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK SHARP & DOHME CORP.; DAI, Xing; LIU, Hong; PALANI, Anandan; HE, Shuwen; BROCKUNIER, Linda L.; NARGUND, Ravi; MARCANTONIO, Karen; ZORN, Nicolas; XIAO, Dong; PENG, Xuanjia; LI, Peng; GUO, Tao; WO2014/121416; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1072448-08-8 , The common heterocyclic compound, 1072448-08-8, name is Methyl 3-amino-5-bromopicolinate, molecular formula is C7H7BrN2O2, 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.

Step 3: methyl 3-amino-5-(benzylsulfanyl)pyridine-2-carboxylate: [00313] A flask containing methyl 3-amino-5-bromopyridine-2-carboxylate (826 mg, 3.57 mmol, Step 2), benzylthiol (630 muL, 5.37 mmol) and DBU (1.6 mL, 10.7 mmol) mixed with N- methylmorpholine (8 mL) was flushed with nitrogen, and the reaction mixture heated at reflux for 40 minutes, with brisk stirring as a second phase forms, then brought to room temperature. The mixture was partially concentrated, treated with 1 M aqueous citric acid (7 mL) and extracted four times with 1:1 CH2Cl2/heptane. The combined organic phases were washed with 1:11 M aqueous citric acid/brine, and the separated aqueous phase was extracted once with 1:1 CH2Cl2/heptane. The organic phases were dried (Na2SO4), combined and filtered with a thorough CH2Cl2 rinse of the solids. The filtrate was concentrated and chromatographed on silica (0 to 10% ethyl acetate in 1:1 CH2Cl2/heptanes) to give the titled compound (518 mg). 1H NMR (500 MHz, DMSO-d6) delta ppm 3.77 (s, 3H), 4.30 (s, 2H), 6.70 (s, 2H), 7.14 (d, J = 2.0 Hz, 1H), 7.24 – 7.28 (m, 1H), 7.31 – 7.35 (m, 2H), 7.40 – 7.43 (m, 2H), 7.73 (d, J = 2.0 Hz, 1H); MS (DCI) m/z 275 (M+H)+.

The synthetic route of 1072448-08-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ABBVIE S.A.R.L.; GALAPAGOS NV; ALTENBACH, Robert, J.; COWART, Marlon, D.; DE MUNCK, Tom, Roger Lisette; DROPSIT MONTOVERT, Sebastien Jean, Jacques Cedric; GFESSER, Gregory, A.; KELGTERMANS, Hans; MARTINA, Sebastien, Laurent Xavier; VAN DER PLAS, Steven, Emiel; WANG, Xueqing; (300 pag.)WO2016/193812; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 56809-84-8, 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. 56809-84-8, name is 3,4-Dichloro-5-nitropyridine. A new synthetic method of this compound is introduced below.

To a solution of NaH (60% in mineral oil, 1.33 g, 33.42 mmol) in DMF (40 mL) at 0 C was added dropwise tert-butyl methyl malonate (5.65 mL, 33.42 mmol) in DMF (10 mL). The mixture was stirred at ft for 30 mm., then 3,4-dichloro-5-nitropyridmne (commercial, 4.3 g, 22.28 mmol) in DMF (10 mL) was added dropwise at 0 C. The reaction mixture was stirred at rt for 6 h, then acidified to pH 3 with a 2N aqueous solution of HCI. The reaction mixture was poured onto ice water and the compound was extracted in Et20. The organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure. The residue waspurified by column chromatography using 20% EtOAc in hexanes to afford 3.83 g of tertbutyl methyl (3-chloro-5-nitropyridin-4-yl)propanedioate a4 as pale yellow solid.Yield: 52%.1H NMR (400 MHz, CDCI3) 6 9.15 (s, 1H), 8.88 (s, 1H), 5.37 – 5.51 (m, 1H), 3.79 (s, 3H),1.46 (s, 9H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,56809-84-8, 3,4-Dichloro-5-nitropyridine, and friends who are interested can also refer to it.

Reference:
Patent; UCB BIOPHARMA SPRL; SKOLC, David; ATES, Ali; JNOFF, Eric; VALADE, Anne; (99 pag.)WO2016/55482; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 139585-70-9, 6-Bromonicotinonitrile, 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, HPLC of Formula: C6H3BrN2, blongs to pyridine-derivatives compound. HPLC of Formula: C6H3BrN2

0.54 g of intermediate 3-1,0.28 g of 2-bromo-5-cyanopyridine, 1.28 g of tripotassium phosphate,And 0.15 g of [1,1-bis (diphenylphosphino) ferrocene] palladium dichloride,10 mL of DME was added. The mixture was stirred at 80 C. for 2 hours,After cooling to room temperature, water was added and the mixture was extracted with ethyl acetate.The obtained organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure.The obtained residue was subjected to silica gel chromatography (hexane: ethyl acetate = 1: 3) to obtain 0.26 g of the active compound A-52 shown below.

The synthetic route of 139585-70-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SUMITOMO CHEMICAL COMPANY LIMITED; MURAKAMI, SHINICHIRO; (291 pag.)JP2018/76354; (2018); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 14237-71-9 , The common heterocyclic compound, 14237-71-9, name is 2-Chloro-4,6-dimethylnicotinonitrile, molecular formula is C8H7ClN2, 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 mixture of the corresponding chloroderivatives (pyridine, pyridazine, coumarin, and nicotinic acid)(10 mmol), selenium metal (1 g, 12 mmol) and sodium borohydride (1.2 g, 32 mmol) in EtOH (50 mL) were stirred till colorless. After that, DMF (20 mL) was added then deep red browncolor appeared. An additional selenium metal (1 g, 12 mmol)was added with EtOH (5 mL). The reaction mixture was reuxedfor 3 hrs., then cooled and poured in ice/HCl. The solid thus separated out was fltered, dried, and recrystallized from ethanol.2,2-Bis(3-cyano-4,6-dimethyl)dipyridyldiselenide (5a): mp244-245C. Data is in agreement with literature survey.20

The synthetic route of 14237-71-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Abdel-Hafez, Shams H.; Abdelwahab, Ahmed B.; Kirsch, Gilbert; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 192; 10; (2017); p. 1114 – 1118;,
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. 102368-13-8, name is 1,1′-Thiocarbonylbis(pyridin-2(1H)-one), the common compound, a new synthetic route is introduced below. name: 1,1′-Thiocarbonylbis(pyridin-2(1H)-one)

(c) N-(2,4-Difluoro-3-isothiocyanato-benzyl)-2,2-dimethyl-propionamide A mixture of N-(3-amino-2,4-difluoro-benzyl)-2,2-dimethyl-propionamide (570 mg, 2.35 mmol), 1,1′-thiocarbonyldi-2(1H)-pyridone (550 mg, 2.35 mmol) and dioxane (20 mL) is stirred at reflux overnight. The reaction mixture is concentrated, diluted with DCM, filtered through a pad of silica gel and the filtrate is concentrated to give the title compound. Yield: 440 mg (65%). Rf=0.80 (silica gel, DCM:EtOH 95:5).

The synthetic route of 102368-13-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; US2012/214786; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 13472-85-0, Adding some certain compound to certain chemical reactions, such as: 13472-85-0, name is 5-Bromo-2-methoxypyridine,molecular formula is C6H6BrNO, 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 13472-85-0.

The mixture of 5-bromo-2-methoxypyridine (15.00 g, 79.78 mmol) and diluted hydrochloric acid (6M, 150 mE) was stirred for 20 hat 100 C. Afier the reaction finished, the mixture was diluted with water (600 mE), adjusted pH to 7 with aq. NaOH solution (iM), and then extracted with EtOAc (200 mE*4). The combined organic phase was washed with sat. aq NaC1 (20 mE), dried over Na2504, filtered and concentrated in vacuo. The residue was mashed with mixed solvents (PE/EtOAc =10/i, 100 mE), filtered and then washed with PE (5 mE*3), dried in vacuo to give compound B-i_2 as white solid (10.42 g, 61.55%). ?H NMR (400 MHz, CDC13) oe: 11.76 (bts., iH), 7.70 (d, J=3.0 Hz, iH), 7.56 (dd, J=2.5, 9.5 Hz, iH), 6.36 (d, J=9.5 Hz, iH).

According to the analysis of related databases, 13472-85-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SHIJIAZHUANG SAGACITY NEW DRUG DEVELOPMENT CO., LTD.; SHIH, Neng-yang; CHEN, Bin; ZHANG, Lei; LI, Jian; CHEN, Shuhui; US2019/62315; (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.127561-18-6, name is 1-(6-(Trifluoromethyl)pyridin-2-yl)piperazine, molecular formula is C10H12F3N3, molecular weight is 231.22, as common compound, the synthetic route is as follows.HPLC of Formula: C10H12F3N3

Add 4- (6-TRIFLUOROMETHYL-2-PYRIDYL) piperazine (46 mg, 0. 2 mmol) to a solution of 4- [6-CHLORO-2- (3-CHLOROPHENYL) PYRIMIDIN-4-YL] morpholine (62 mg, 0. 2 mmol), PD2 (dba) 3 (18 mg, 0. 02 MMOL), and BINAP (17 mg, 0. 02 mmol) in toluene (2 mL) under nitrogen, followed by t-BuOK (45 mg, 0. 4 mmol). Stir the mixture at 90C for 8 hours, dilute with aqueous ammonium chloride, and extract with EtOAc (3 x 10 mL). Dry (MGS04) the combined extracts and concentrate under reduced pressure. Purify the residue using flash chromatography on silica gel (50% hexane/50% ether) to give the title compound. MS 505 (M+ 1).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,127561-18-6, 1-(6-(Trifluoromethyl)pyridin-2-yl)piperazine, and friends who are interested can also refer to it.

Reference:
Patent; NEUROGEN CORPORATION; WO2005/7648; (2005); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 59207-23-7, 2-Methylthieno[3,2-c]pyridin-4(5H)-one, 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, 59207-23-7, blongs to pyridine-derivatives compound. Application In Synthesis of 2-Methylthieno[3,2-c]pyridin-4(5H)-one

7-bromo-2-methyIthieno [3,2-cl pyridin-4(5//)-one; To a solution of 2-methylthieno [3,2- c]pyridin-4(5H)-one (4.84 g, 28.9 mmol) in acetic acid (84.0 mL) is added bromine drop wise (1.64 mL, 31.8 mmol). The reaction mixture is heated to reflux for one hour. After one hour, the solution is cooled to rt, and water is added until a solid is formed. The remaining solid is filtered, rinsed with water, and dried under vacuum to afford the title compound (6.01 g, 85% yield). 1H NMR delta 11.7 (br s, IH), 7.47 (s, IH), 7.30 (s, IH), 3.38 (s, 3H). LCMS (ES, M+H=245).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,59207-23-7, its application will become more common.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2006/106326; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem