Tag: M.W:200-300

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.183208-22-2, name is 5-Bromo-1-methyl-1H-pyrrolo[2,3-b]pyridine, molecular formula is C8H7BrN2, molecular weight is 211.06, as common compound, the synthetic route is as follows.SDS of cas: 183208-22-2

To a solution of tert-butyl (S)-2-(methoxymethyl)pyrrolidine-1-carboxylate (663 mg, 3.08mmol) in DCM (10 mL) was added trifluoroacetic acid (1.76 g, 15.40 mmol) within 5 min at0C. The mixture was warmed up to room temperature within 2 h and carefully poured into a10% NaOH solution (60 mL). After extraction with DCM (2 × 50 mL) the combined organicphases were dried over MgSO4, and evaporated. The residue was dissolved in DCM (5 mL)and N,N-diisopropylethylamine (521 mg, 4.03 mmol) was added at room temperature. Thissolution containing the deprotected pyrrolidine was then stirred until it was needed.A two-neck flask was charged with 5-bromo-1-methyl-1H-pyrrolo[2,3-b]pyridine (3)(500 mg, 2.37 mmol) and dry THF (30 mL) under argon. The solution was cooled to -80 C inan ethanol/nitrogen cooling bath and t-BuLi (1.4 M in pentane, 1.69 mL, 2.37 mmol) wasS 6added dropwise. The reaction mixture was warmed up to -75 C within 10 min and transferredto a solution of DABCO-bis(sulfur dioxide) (569 mg, 2.37 mmol) in dry THF (15 mL) at -75C. The cooling bath was removed after 30 min and the reaction mixture warmed up to roomtemperature. The THF solvent was removed under reduced pressure and dry DCM (20 mL)was added. N-Chlorosuccinimide (379 mg, 2.84 mmol) was slowly added as a solution in dryDCM (5 mL) followed by dropwise addition of the deprotected pyrrolidine. After the additionof water (35 mL) the mixture was extracted with DCM (2 × 20 mL). The combined organicphases were dried over MgSO4, and evaporated. Column chromatographic purification (SiO2,CH/EtOAc, 2:1) yielded a colorless, crystalline solid [291 mg, 40% yield].MP: 66 – 67 C (CH/EtOAc).1H-NMR (300 MHz, CDCl3): delta = 1.50-1.60 (m, 2H, 13-CHa, 14-CHa), 1.79-1.89 (m, 2H,13-CHb, 14-CHb), 3.08-3.18 (m, 1H, 15-CHa), 3.34-3.42 (m, 1H, 16-CHa), 3.38 (s, 3H,18-CH3), 3.44-3.52 (m, 1H, 15-CHb), 3.68 (dd, 2JH,H = 9.2 Hz, 3JH,H = 3.8 Hz, 1H, 16-CHb),3.71-3.81 (m, 1H, 12-CH), 3.95 (s, 3H, C-19), 6.60 (d, 3JH,H = 3.5 Hz, 1H, 3-CH), 7.33 (d,3JH,H = 3.5 Hz, 1H, 2-CH), 8.39 (d, 4JH,H = 2.1 Hz, 1H, 4-CH), 8.80 (d, 4JH,H = 2.1 Hz, 1H,6-CH) ppm.13C-NMR (75 MHz, CDCl3): delta = 24.1 (t, C-14), 28.9 (t, C-13), 31.7 (q, C-19), 49.5 (t, C-15),59.1 (q, C-18), 59.3 (d, C-12), 75.3 (t, C-16), 101.2 (d, C-3), 119.7 (s, C-9), 125.7 (s, C-5),129.0 (d, C-2), 131.7 (d, C-4), 142.0 (d, C-6), 149.0 (s, C-8) ppm.ESI(+)-MS: calcd. for C14H19N3O3S + H+, 310.1220; found 310.1220.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,183208-22-2, 5-Bromo-1-methyl-1H-pyrrolo[2,3-b]pyridine, and friends who are interested can also refer to it.

Reference:
Article; Waldmann, Christopher M.; Hermann, Sven; Faust, Andreas; Riemann, Burkhard; Schober, Otmar; Schaefers, Michael; Haufe, Guenter; Kopka, Klaus; Bioorganic and Medicinal Chemistry; vol. 23; 17; (2015); p. 5734 – 5739;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1028-86-0, Adding some certain compound to certain chemical reactions, such as: 1028-86-0, name is N-(2-Chloropyridin-3-yl)-2-nitrobenzamide,molecular formula is C12H8ClN3O3, 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 1028-86-0.

Stage B: 2-(2-nitrophenyl)oxazolo[5,4-b]pyridine Using the procedure described in Example 1, but replacing 3-benzoylamino-2-chloropyridine by 3-(2-nitrobenzoylamino)-2-chloropyridine obtained in stage A. Yield: 77% Recrystallization solvent: ether/cyclohexane Melting point: 125 C.

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. 1028-86-0, N-(2-Chloropyridin-3-yl)-2-nitrobenzamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Science et Organisation; US5077408; (1991); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 55304-75-1, 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. 55304-75-1, name is 2,6-Dichloro-3-(trifluoromethyl)pyridine, molecular formula is C6H2Cl2F3N, 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.

A suspension of 3-(R)-methyl-1-trityl-piperazine (from Example 4; 7.80 g, 22.9 mmol), 2,6-dichloro-3-trifluoromethylpyridine (4.50 g, 20.8 mmol) and K2CO3 (4.0 g, 29 mmol) in DMSO (100 mL) was stirred at 80 C. over night. A mixture of EtOAc/toluene (50:50; 500 mL) was added to the filtered solution and the mixture were washed three times with water (1 L). The dried (MgSO4) organic phase was concentrated under reduced pressure and the resulting brown oil was dissolved in heptane/EtOAc (90:10) and filtered through a plug (6060 mm) of silica. Slow evaporation of about two thirds of the solvent at reduced pressure afforded light yellow crystals (6.11 g, 56%). Purity 100% (HPLC); mp 209 C. Fragmenting MS analysis supports the stated structure. Anal. (C30H27ClF3N3) C, H, N.

According to the analysis of related databases, 55304-75-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Nilsson, Bjorn M.; Ringberg, Erik; US2003/232814; (2003); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 887147-19-5, 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 887147-19-5 as follows.

General procedure: Similar to as described in General Procedure U, 4,6-dichloro-1-methyl-1H-imidazo[4,5-c]pyridine was reacted with potassium(R)-trifluoro(3 -((3-hydroxy- 1 -methyl-2-oxopyrrolidin-3-yl)ethynyl)phenyl)borate to give the titlecompound (80 mg, 20%) as a yellow solid. LC-MS (ES, m/z): 381 [M+H]. A tube containing a solution of arylchloride/bromide (1 eq) and aryltrifluoroborate (1 eq) in Ethanol was purged with nitrogen before addition of Pd(OAc)2 (0.06 eq), RuPhos (0.12 eq), and Sodium Carbonate (2 eq). The tube was sealed with a cap lined with a disposable Teflon septum was heated at 85 C for 12-20 hours. The reaction mixture was allowedto cool to room temperature and was either filtered through Celite and submitted directly to reverse phase HPLC purification or extracted with dichloromethane and a solution of saturated ammonium chloride before drying, evaporating and submitting to reverse phase purification or using in the subsequent step without purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,887147-19-5, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; BLAQUIERE, Nicole; BURCH, Jason; CASTANEDO, Georgette; FENG, Jianwen A.; HU, Baihua; LIN, Xingyu; STABEN, Steven; WU, Guosheng; YUEN, Po-wai; WO2015/25026; (2015); 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 73335-64-5, name is 1-(5-Bromopyridin-3-yl)-N-methylmethanamine. This compound has unique chemical properties. The synthetic route is as follows. Application In Synthesis of 1-(5-Bromopyridin-3-yl)-N-methylmethanamine

Step B Tert-butyl((5-bromopyridin-3-yl)methyl)(methyl)carbamate (31b)To a stirred solution of 31a (1 g, 4.97 mmol) in methanol (10 mL) triethylamine (3.3 mL, 24.8 mmol ) was added at 0C followed by the drop wise addition of Boc anhydride (1.7 mL, 7.5 mmol). The reaction mixture was stirred overnight at room temperature under nitrogen atmosphere. The reaction mixture was concentrated under reduced pressure. The residue was diluted with ethyl acetate, successively washed with water and brine. The organic layer was dried over anhydrous Na2SO4, evaporated to dryness under reduced pressure to obtain 31b (800 mg) as colorless gummy mass. 1H NMR (400 MHz, CD3OD): delta 8.59 (d, J=1.80 Hz, 1H), 8.43 (d, J=1.50 Hz, 1H), 7.92 (t, J=2.00 Hz, 1H), 4.47 (s, 2H), 2.91 (s, 3H), 1.46 (s, 9H). Molecular Formula: C12H17Br2O2; LC- MS purity: 98.4%; Expected: 301.1; Observed: 301.1 (M).

With the rapid development of chemical substances, we look forward to future research findings about 73335-64-5.

Reference:
Patent; MERCK SHARP & DOHME CORP.; BARR, Kenneth, Jay; SCOTT, Mark, E.; THOMPSON, Christopher, F.; ANTHONY, Neville; CAMMARANO, Carolyn, Michelle; BAKSHI, Raman, Kumar; MOHANTY, Subhendu, Kumar; KORAPALA, Chandra, Sekhar; LATTHE, Prashant, R.; KAMBAM, Vyjayanthi, N.; SARKAR, Sujit, Kumar; THATAI, Jayanth, Thiruvellore; WO2015/50798; (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. 157329-89-0, name is 2-Bromo-6-chloro-4-methylpyridine, molecular formula is C6H5BrClN, 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. Product Details of 157329-89-0

b) 4-Methyl-2,6-bis-(4-trifluoromethylphenyl)-pyridine To a degassed solution of 2-bromo-6-chloro-4-methyl-pyridine (1.45 g, 7.04 mmol), 4-trifluoromethylbenzeneboronic acid (3.8 g, 20 mmol), 2N Na2CO3 (10 mL) in DME (80 mL) was added tetrakis(triphenylphosphine)palladium (690 mg, 0.6 mmol) under argon. The mixture was heated to 85 C. for 4 h, cooled to room temperature, diluted with water, and extracted with methylene chloride (3*). The organic solution was washed with brine, dried over Na2SO4, and concentrated. The residue was purified by column chromatography on silica gel (0-20% methylene chloride in heptane) to give the product as an off white solid (1.75 g, 65%). 1H NMR (300 MHz, CDCl3) delta 8.24 (d, J=7.91 Hz, 26H), 7.75 (d, J=8.29 Hz, 26H), 7.61 (s, 13H), 2.53 (s, 19H). MS m/e 382.2 (M+H)

With the rapid development of chemical substances, we look forward to future research findings about 157329-89-0.

Reference:
Patent; Lu, Tianbao; US2010/22583; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 571188-59-5, 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 571188-59-5 as follows.

General procedure: To a solution of alcohol (1.1 mmol) in a mixture of solvents EtOAc: DMSO (4 ml: 2 ml), was added T3P (2.5 mmol, 50% solution in ethyl acetate) at 0 C, and the resulting mixture was stirred at room temperature for 1-2 h under nitrogen atmosphere. The reaction was monitored by TLC, amine (1.0 mmol) and thioglycolic acid (1.0 mmol) were added once and stirred further for 1-3 h at room temperature. After completion of the reaction, the mixture was diluted with water (20 ml) and neutralized by adding 10% NaHCO3 solution. The product was extracted with ethyl acetate (10 ml 2) and the combined organic layers were washed with water followed by brine solution. The organic phase was dried over anhydrous Na2SO4. The solvent was removed under reduced pressure to afford a crude product which was purified by column chromatography using hexane: ethyl acetate mixture (8:2) as an eluent.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,571188-59-5, its application will become more common.

Reference:
Article; Sharath Kumar, Kothanahally S.; Swaroop, Toreshettahally R.; Harsha, Kachigere B.; Narasimhamurthy, Kereyagalahally H.; Rangappa, Kanchugarakoppal S.; Tetrahedron Letters; vol. 53; 42; (2012); p. 5619 – 5623;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 874959-68-9, 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 874959-68-9, name is 5-Bromopyridine-2-sulfonyl chloride. This compound has unique chemical properties. The synthetic route is as follows.

A mA mixture of 5-bromo-2-pyridinesulfonyl chloride (0.30Og, 1.17mmol), pyrrolidine (0.0976ml, 1.17mmol) and TEA (0.326ml, 2.34mmol) in anhydrous DCM (6ml) was stirred at room temperature under nitrogen overnight. The reaction mixture was partitioned between DCM (20ml) and water (20ml), the layers separated and the DCM extract evaporated in vacuo to give the title compound as a pale brown solid (0.367g).MH+ = 293, rt = 2.74 min

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 874959-68-9, 5-Bromopyridine-2-sulfonyl chloride.

Reference:
Patent; GLAXO GROUP LIMITED; WO2008/145688; (2008); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 75806-84-7, 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. 75806-84-7, name is 2-Bromo-3-chloro-5-(trifluoromethyl)pyridine. A new synthetic method of this compound is introduced below.

Example 63 10-Chloro-1-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]-7-(1-ethylpropyl)-2,3,4,5-tetrahydro-1H-[1,3]diazepino[1,2-a]benzimidazole A mixture of 10-chloro-7-(1-ethylpropyl)-2,3,4,5-tetrahydro-1H-[1,3]diazepino[1,2-a]benzimidazole (Reference Example 72; 150 mg, 0.51 mmol), 2-bromo-3-chloro-5-(trifluoromethyl)pyridine (401 mg, 1.54 mmol), copper(I) iodide (97 mg, 0.51 mmol), 2,2′-bipyridyl (159 mg, 1.02 mmol) and cesium carbonate (333 mg, 1.02 mmol) in 1-methyl-2-pyrrolidinone (2.0 mL) was stirred at 150 C. for 16 hr. The mixture was diluted with ethyl acetate, filtered through a pad of celite, washed with 2N hydrochloric acid, water and brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by flash chromatography on silica gel eluding with a 5-20% ethyl acetate/n-hexane gradient mixture. The filtrate was concentrated in vacuo to give a residue, which was purified by preparative HPLC to give a solid, which was recrystallized from n-hexane/ethyl acetate to give the title compound (104 mg, 0.221 mmol, 43%) as a colorless solid. mp 108-110 C. 1H NMR (CDCl3) delta 0.87 (t, J=7.3 Hz, 6H), 1.67-2.13 (m, 8H), 3.02-3.19 (m, 1H), 4.18-4.28 (m, 2H), 4.48-4.56 (m, 2H), 6.99 (d, J=8.3 Hz, 1H), 7.21 (d, J=8.3 Hz, 1H), 7.73-7.85 (m, 1H), 8.43-8.57 (m, 1H). MS Calcd.: 470; Found: 471 (M+H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,75806-84-7, 2-Bromo-3-chloro-5-(trifluoromethyl)pyridine, and friends who are interested can also refer to it.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; US2009/186879; (2009); 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. 1201326-81-9, name is Methyl 5-(methylsulfonyl)picolinate. This compound has unique chemical properties. The synthetic route is as follows. Application In Synthesis of Methyl 5-(methylsulfonyl)picolinate

Compound 3 (8.6 g, 20 mmol) was added to methanol/water (60 mL / 20 mL)And LiOH (3.3 g, 80 mmol). The reaction mixture was stirred at room temperature for 2 hours.The reaction mixture was acidified to pH = 6, and the precipitate was separated by filtration.The filtered precipitate was dissolved in dichloromethane (100 mL) and a catalytic amount of DMF was added.Then, oxalyl chloride (6.8 g, 54 mmol) was slowly added dropwise at 0 C.The temperature was raised to room temperature and held for 2 hours. Then remove the solvent,The mixture was dissolved in CH 2 Cl 2 (100 mL).Et3N (13.8 mL, 108 mmol) was added.Stir for 5 minutes,N,O-Dimethylhydroxylamine hydrochloride (5.3 g, 54 mmol) was added.The reaction was continued to stir at room temperature for 30 minutes.Water (40 mL) was added to the reaction mixture and water was applied sequentially.Wash with saturated brine. The organic phase was collected and dried over anhydrous MgSO4.The solvent was removed to give the product 4 (7.3 g, 82%).

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, 1201326-81-9, Methyl 5-(methylsulfonyl)picolinate.

Reference:
Patent; Beijing Yuan Bo Fang Pharmaceutical Technology Co., Ltd.; Li Jing; (26 pag.)CN104926797; (2019); B;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem