Tag: M.W:200-300

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. 183208-34-6, name is 5-Bromo-1H-pyrrolo[2,3-b]pyridin-2-one, the common compound, a new synthetic route is introduced below. name: 5-Bromo-1H-pyrrolo[2,3-b]pyridin-2-one

Step 3: 5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-lH-pyrrolo[2,3-b]pyridin-2(3H)-one To a solution of 5-bromo-lH-pyrrolo[2,3-b]pyridin-2(3H)-one (3 g, 14.08 mmol) in 1,4-dioxane (60 mL) were added 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi(l,3,2-dioxaborolane) (4.29 g, 16.9 mmol), potassium acetate (2.07 g, 21.12 mmol) and l,l’-bis(diphenylphosphino)ferrocene- palladium(II)dichloride (1.02 g, 1.41 mmol). The reaction mixture was purged with nitrogen for 2 min and heated to 110 C for 1 h. After cooling down the mixture was filtered and the solid was washed with ethyl acetate. The mother liquid was diluted with methanol and the precipitate was filtered and dried in vacuo to afford 5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-lH-pyrrolo[2,3- b]pyridin-2(3H)-one (1.1 g, 30%): lU NMR (400 MHz, DMSO-d6) delta 11.14 (s, 1H), 8.29 (s, 1H), 7.68 (s, 1H), 3.54 (s, 2H), 1.29 (s, 12H).

The synthetic route of 183208-34-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; ESTRADA, Anthony; HUESTIS, Malcolm; KELLAR, Terry; PATEL, Snahel; SHORE, Daniel; SIU, Michael; (260 pag.)WO2016/142310; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1060814-91-6 ,Some common heterocyclic compound, 1060814-91-6, molecular formula is C9H10BrNO2, 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.

[0567] Step 2: ethyl 2-(4-bromopyridin-2-yl)-2-methylpropanoate – To a stirred solution of ethyl 2-(4-bromopyridin-2-yl)acetate (0.5 g, 2.05 mmol, 1.0 eq) in D F (5 mL) at 0C under nitrogen atmosphere was added NaH (60%) (0.246 g, 6.10 mmol, 3 eq). The reaction mass was stirred at rt for 30 mins, then cooled to 0C followed by the addition of methyl iodide (1.486 g, 10.25 mmol, 5.0 eq) under nitrogen atmosphere and stirred at RT for 16h. The DMF was removed under reduced pressure, water (10 mL) was added and the product extracted into EtOAc (3×15 mL). The combined organic extracts were dried over anhydrous sodium sulfate and concentrated under reduced pressure to give a crude product which was purified by column chromatography to give ethyl 2-(4-bromopyridin-2-yl)-2-methylpropanoate (0.140g, 25%) as a pale yellow liquid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1060814-91-6, its application will become more common.

Reference:
Patent; CAPULUS THERAPEUTICS, LLC; GREEN, Michael John; HART, Barry Patrick; (341 pag.)WO2019/148125; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1018505-59-3, 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. 1018505-59-3, name is 5-(4-Ethylpiperazin-1-yl)pyridin-2-amine, molecular formula is C11H18N4, 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.

Add to the reaction flask7- (2-chloro)Fluoro-pyrimidin-4-yl) -5-fluoro-2,3-dihydro-1H-benzo [d]Pyrrole [1,2-a] imidazole(200 mg, 0.6 mmol, prepared according to the procedure of Example 1)5- (4-ethylpiperazin-1-yl) pyridin-2-amine (123 mg, 0.6 mmol, prepared in second step)Cesium carbonate (390 mg, 1.2 mmol), Pd2 (dba) 3 (55 mg, 0.06 mmol)XantPhos (35 mg, 0.06 mmol) and anhydrous 1,4-dioxane (5 mL).The mixture was stirred at 120 C for 12 hours.Cooled to room temperature, water (10 mL) and ethyl acetate (20 mL x 3) were added to the solution.The combined organic phases were washed with saturated sodium chloride solution (20 mL), dried over anhydrous sodium sulfate,Filtered, concentrated under reduced pressure. The residue was purified by column chromatography (DCM / MeOH = 10: 1)The resulting residue was purified to give the title compound (50 mg, white solid)Yield 17%.

According to the analysis of related databases, 1018505-59-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Gan & Lee Pharmaceuticals; Liu, Wenjian; Yin, Lei; Li, Heng; (94 pag.)CN106608879; (2017); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1018505-59-3, 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 1018505-59-3, name is 5-(4-Ethylpiperazin-1-yl)pyridin-2-amine. This compound has unique chemical properties. The synthetic route is as follows.

A reaction flask was charged with 321 mg (1 mmol) of 5-(2-chloro-5-fluoropyrimidin-4-yl)-3-ethyl-7-fluoro-2,3-dimethyl-3H-indole prepared in Step 3, 206 mg (1 mmol) of 5-(4-ethylpiperazin-1-yl)pyridin-2-amino obtained in Step 2, 2 ml of 1,4-dioxane, 650 mg (2 mmol) of Cs2CO3, 91mg (0.1mmol) of Pd2(dba)3, and 58mg (0.1mmol) of diphenylphosphine. The mixture was heated to 120C to conduct microwave reaction for 1 h. The reaction product was cooled to room temperature, added with 10ml of water and then extracted with ethyl acetate three times (40ml for each time). The organic phases were combined, washed once with 40 ml of saturated salt solution, dried with sodium sulfate, filtered, concentrated under reduced pressure and separated by silica gel column chromatography (DCM/MeOH = 10:1) to give the titled compound (49 mg, yellow solid), yield 10%. 1H-NMR(400MHz, CDCl3) delta9.25(br s, 1H), 8.46(d, 1H, J=3.2Hz), 8.28(d, 1H, J=9.2Hz), 8.17(d, 1H, J=2.0Hz), 7.90(d, 1H, J=11.2Hz), 7.82(s, 1H), 7.35(dd, 1H, J=9.2Hz, 2.8Hz), 3.20-3.18(m, 4H), 2.64-2.61(m, 4H), 2.51(q, 2H, J=6.8Hz), 2.31(s, 3H), 2.03-1.94(m, 1H), 1.89-1.82(m, 1H), 1.36(s, 3H), 1.13(t, 3H, J=7.2Hz), 0.48(t, 3H, J=7.2Hz). MS(ESI):m/z 492.3[M+H]+.

According to the analysis of related databases, 1018505-59-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Gan & Lee Pharmaceuticals; YIN, Lei; LIU, Wenjian; LI, Heng; ZHU, Dianxi; (73 pag.)EP3385262; (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. 1401624-81-4, name is 2,6-Dibromo-[1,2,4]triazolo[1,5-a]pyridine. A new synthetic method of this compound is introduced below., Recommanded Product: 2,6-Dibromo-[1,2,4]triazolo[1,5-a]pyridine

General procedure: d) 6-Bromo-2-morpholin-4-yl-[ 1 ,2,4] triazolo[ 1 ,5-a]pyridine A mixture of 2,6-dibromo-[l,2,4]triazolo[l,5-a]pyridine (1 g, 3.61 mmol) and morpho- line (10 g, 10 ml, 115 mmol) was refluxed for 4 hours under argon atmosphere. The mixture was evaporated to dryness under reduced pressure. Flash chromatography (silica gel, 50 g, 30-100% heptane/ethyl acetate) afforded 6-bromo-2-morpholin-4-yl-[l,2,4]triazolo[l,5-a]pyridine (672 mg, 66%) as a light yellow solid. Mp.: 136C. MS: m/z=283.0/285.0 (M+H+).

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, 1401624-81-4, 2,6-Dibromo-[1,2,4]triazolo[1,5-a]pyridine.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; FLOHR, Alexander; GROEBKE ZBINDEN, Katrin; KOERNER, Matthias; WO2013/41472; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1227573-02-5 ,Some common heterocyclic compound, 1227573-02-5, molecular formula is C6H3BrFNO, 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: 2-Chloro-4-(5-fluoro-4-formyl-pyridin-3-yl)-benzonitrile (15c)To the solution of 2-chloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile (264 mg, 1.00 mmol), 3-bromo-5-fluoroisonicotinaldehyde (204 mg, 1.00 mmol) and PdCI2(PPh3)2 (56 mg, 0.08 mmol) in DMF (3 mL) was added 2M Na2C03 solution (1.50 ml, 3.00 mmol) under nitrogen atmosphere. The mixture was stirred and heated at 100C for 4hrs. After letting cool to room temperature, solvent was removed in vacuo. The resulting residue was dissolved in DCM and saturated NH4CI solution. After extraction and separation, the combined extracts were concentrated and purified by SNAPI Og (10%MeOH/DCM 0- 15%gradient) to give 2-chloro-4-(5-fluoro-4-formylpyridin-3-yl)benzonitrile (47 mg, 18%) as a white solid.; ESI-MS m/z: 293 [M+MeOH+1]+, Retention time 1.15min. -NMR (CDCI3, 400 MHz) delta 7.33 (dd, J= 8.0, 1.6 Hz, 1 H), 7.50 (d, J= 1.6 Hz, 1 H), 7.78 (d, J= 8.0 Hz, 1 H), 8.49 (s, 1 H), 8.78 (d, J= 1.2 Hz, 1H), 10.27 (s, 1H)

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. 1227573-02-5, 3-Bromo-5-fluoroisonicotinaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NOVARTIS AG; ALLAN, Martin; CHAMOIN, Sylvie; HU, Qi-Ying; IMASE, Hidetomo; PAPILLON, Julien; WO2011/61168; (2011); 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. 685517-67-3, name is 2,6-Difluoro-3-iodopyridine. This compound has unique chemical properties. The synthetic route is as follows. Computed Properties of C5H2F2IN

n-Butyllithium (1.66mL, 4.15mmol, 2.5mol/L in hexane) was added dropwise to a solution of diisopropylamine (1.30mL, 4.15mmol) in THF (2mL) at -78C. After 25min 2,6-difluoro-3-iodopyridine (1.00g, 4.15mmol) in THF (5mL) was added dropwise into this mixture by cannula. After 12h at -78C, H2O (0.2mL, 11mmol) in THF (2mL) was added and the mixture was warmed to room temperature during 1h. The mixture was washed with 10% aqueous Na2SO3 (5mL) and extracted with ethyl acetate (3×50mL). The organic extracts were dried (MgSO4) and concentrated in vacuo. Crystallization from hexane afforded the product as colorless crystals (740mg, 74%). 1H NMR (400MHz, CDCl3): delta 7.22 (t, 2H,J=1.2). 13C NMR (100MHz, CDCl3): 161.1 (dd, J=250, 16, 2C), 115.6 (dd, J=24, 10, 2C), 110.3. 19F NMR (376MHz, CDCl3): delta -68.1. GC-MS m/z calcd. for C5H2F2IN [M+]: 241, found: 241. MP: 78-80C.

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, 685517-67-3, 2,6-Difluoro-3-iodopyridine.

Reference:
Article; Jin, Xin; Cramer, Jacob R.; Chen, Qi-Wei; Liang, Hai-Lin; Shang, Jian; Shao, Xiang; Chen, Wei; Xu, Guo-Qin; Gothelf, Kurt V.; Wu, Kai; Chinese Chemical Letters; vol. 28; 3; (2017); p. 525 – 530;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 885277-48-5, 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. 885277-48-5, name is Methyl 2-bromo-6-methylnicotinate. A new synthetic method of this compound is introduced below.

To a solution of methyl 2-bromo-6-methyl-3-pyridinecarboxylate D60 (1.15 g) and Pd(Ph3P)4 (0.2 g, 0.173 mmol) in 1,4-Dioxane (10 ml) stirred under nitrogen at room temperature tributyl(ethenyl)stannane (1.74 g, 5.50 mmol) was added neat in one charge. The reaction mixture was stirred at microwave Personal Chemistry at 95 C. for 30 minutes. The solvent was removed to give the crude title compound. Under similar conditions another batch of D60 (100 mg) was processed to give the crude title compound. The two crudes were joined and purified by flash chromatography on silica (80 g column, gradient elution from Cy to Cy/EtOAc 4:6) to afford the title compound D61 (1.0 g). UPLC (Basic GEN_C): rt=0.73 minutes, peak observed: 178 (M+1). C10H11NO2 requires 177. 1H NMR (400 MHz, CDCl3) delta ppm 8.08 (d, 1H), 7.66 (dd, 1H), 7.12 (d, 1H), 6.52 (d, 1H), 5.59 (dd, 1H), 3.93 (s, 3H), 2.63 (s, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,885277-48-5, Methyl 2-bromo-6-methylnicotinate, and friends who are interested can also refer to it.

Reference:
Patent; ALVARO, Giuseppe; Amantini, David; Castiglioni, Emiliano; Di Fabio, Romano; Pavone, Francesca; US2010/144760; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 89167-34-0, 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. 89167-34-0, name is 4-Chloro-3-iodopyridine. A new synthetic method of this compound is introduced below.

Step 1. 4-(2-fluoro-4-nitrophenoxy)-3-iodopyridine (52)[00376] To a stirred solution of 47 (346 mg, 1.445 mmol) in diphenyl ether (6 ml) was added sodium carbonate (459 mg, 4.34 mmol) and 2-fluoro-4-nitrophenol (681 mg, 4.34 mmol). The reaction mixture was heated to 17O0C for four hours then cooled-down to room temperature. The reaction mixture was diluted with dichloromethane, filtered and concentrated. The crude residue was purified by flash column chromatography on silica gel (0% to 35% EtOAc in hexanes) to afford the title compound 52 (400 mg, 1.1 11 mmol, 77%) as a yellow solid. MS: 361.0 (M+ 1).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,89167-34-0, 4-Chloro-3-iodopyridine, and friends who are interested can also refer to it.

Reference:
Patent; METHYLGENE, INC.; RAEPPEL, Stephane; SAAVEDRA, Oscar; CLARIDGE, Stephen; VAISBURG, Arkadii; GAUDETTE, Frederic; ISAKOVIC, Ljubomir; DEZIEL, Robert; WO2008/46216; (2008); A1;,
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. 76041-79-7, name is 5-Bromo-3-(trifluoromethyl)pyridin-2-ol, the common compound, a new synthetic route is introduced below. HPLC of Formula: C6H3BrF3NO

Step 1 : 5-Bromo-2-chloro-3-(trifluoromethv0pyridine (P46a)A solution of compound P45a (11.0 g, 45.8 mmol) in phenylphosphonicdichloride (22 mL) was heated at 140C overnight, cooled to rt, poured into ice water and extracted with EA. The organic layer was washed with sat. aq. NaHC03 and brine consecutively, dried over NaS04, filtered, concentrated and purified by CC (PE/EA = 5/1) to give compound P46a (10.5 g, 88%) as a yellow liquid.

The synthetic route of 76041-79-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PHENEX PHARMACEUTICALS AG; STEENECK, Christoph; KINZEL, Olaf; GEGE, Christian; KLEYMANN, Gerald; HOFFMANN, Thomas; WO2012/139775; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem