Tag: M.W:100-200

Related Products of 766-16-5, 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 766-16-5, name is 4-Fluoro-2-methylpyridine. This compound has unique chemical properties. The synthetic route is as follows.

A suspension of l-cyclopropyl-6-(lH-imidazol-4-yl)-3,3-dimethyl-lH-pyrrolo[3,2-c]pyridin- 2(3H)-one (80 mg), 4-fluoro-2-methylpyridine (42 mg) and cesium carbonate (185 mg) in acetonitrile (1 ml) was heated to reflux temperature for 3 h. The mixture was evaporated and the residue purified by flash chromatography (silica gel, 0% to 10% MeOH in dichloromethane) to give the title compound (59 mg, 55%) as a white foam. MS (ESI, m/z): 360.3 [(M+H)+].

According to the analysis of related databases, 766-16-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; HILPERT, Hans; KOLCZEWSKI, Sabine; LIMBERG, Anja; STOLL, Theodor; WO2015/177110; (2015); 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. 74115-12-1, name is 5-Chloro-3-hydroxypyridine. A new synthetic method of this compound is introduced below., HPLC of Formula: C5H4ClNO

EXAMPLE 3 Synthesis of 5-Chloro-3-pyridinyl trifluoromethanesulfonate Trifluoromethanesulfonic anhydride (5.0 mL, 30 mmol) was dissolved in CH2Cl2 (100 mL), and cooled to 0 C. 5-Chloro-3-pyridinol (3.10 g, 23.9 mmol), and triethylamine (6.5 mL, 47 mmol) were dissolved in CH2Cl2 (50 mL), and the resulting solution was added to the cold trifluoromethanesulfonic anhydride solution dropwise via cannula. The resulting dark brownish-red solution was stirred at 0 C. for 5 minutes, and then the ice bath was removed and the reaction mixture was allowed to warm to ambient temperature. After stirring for 16 h at ambient temperature the reaction was quenched by pouring into water and basified by addition of saturated aqueous sodium carbonate. The basic aqueous phase was extracted with CH2Cl2 (2*50 mL), the combined organics dried over Na2SO4, filtered and concentrated in vacuo. The resulting black viscous oil was filtered through a plug of silica gel and fractions were collected while eluding with 1:1 hexane:ethyl acetate. Fractions containing the desired product were combined, concentrated in vacuo, and further purified by column chromatography eluding with 15:1 then 10:1 hexane:ethyl acetate to afford 5-chloro-3-pyridinyl trifluoromethanesulfonate (3.68 g, 59% yield) as a golden liquid. 1H NMR (CDCl3, 300 MHz) Delta8.65 (d, J=2 Hz, 1H), 8.52 (d, J=2 Hz, 1H), 7.70 (t, J=3 Hz, 1H). MS (ESI) 261 (M+, 35Cl), 263 (M+, 37Cl).

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, 74115-12-1, 5-Chloro-3-hydroxypyridine.

Reference:
Patent; Cosford, Nicholas D.; Roppe, Jeffrey R.; Tehrani, Lida R.; Smith, Nicholas D.; Stearns, Brian; Huang, Dehua; Wang, Bowei; US2005/43307; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 86649-57-2, Adding some certain compound to certain chemical reactions, such as: 86649-57-2, name is 3-Pyridyloxyacetic acid,molecular formula is C7H7NO3, 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 86649-57-2.

Add slowly 1-propanephosphonic acid cyclic anhydride (122.30 g, 100.00 mL,192.18 mmol) to a solution of 2-hydroxy-2-methyl-N-( 1,2,3 ,4-tetrahydroisoquinolin-6-yl)propane-1-sulfonamide hydrochloride (46.90 g, 146.18 mmol), 2-(3-pyridyloxy)acetic acid (27.00 g, 176.31 mmol), dimethylformamide (708.98 g, 750.00 mL, 9.70 mol), triethylamine (59.53 g, 82.00 mL, 588.31 mmol) at 0 C. Allow the reaction to warm slowly to room temperature and stir overnight. Add saturated aqueous sodium sulfate solution (500 mL) and water (500 mL). Extract with dichloromethane (3 xl L), combine the organic layers, dry over anhydrous sodium sulfate, filter and concentrate underreduced pressure. Purify by silica gel chromatography eluting with a mobile phase of dichloromethane/methanol (0% to 10% methanol over 90 minutes). Combine fractions containing a mixture of peaks from previous purification and purify by silica gel chromatography eluting with a mobile phase of dichloromethane/methanol (0% to 10% methanol over 45 minutes) to afford the title compound (8.00 g, 19.05 mmol).Combine the two fractions to afford the title compound (38.00 g, 90.58 mmol). MS (m/z): 420 (M+1).

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. 86649-57-2, 3-Pyridyloxyacetic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ELI LILLY AND COMPANY; BURKHOLDER, Timothy Paul; DEL PRADO, Miriam Filadelfa; FERNANDEZ, Maria Carmen; HEINZ II, Lawrence Joseph; PRIETO, Lourdes; ZHAO, Genshi; WO2015/54060; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 124433-70-1, 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. 124433-70-1, name is 6-Fluoropyridine-2-sulfonamide, molecular formula is C5H5FN2O2S, 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.

6-Chloro-2-(2,4,6-trimethylphenoxy)pyridine-3-carboxylic acid (23.7 g, 81.4 mmol) was added to a mixture of N-[(dimethylamino)-1H-1,2,3-triazolo-[4,5-b]pyridin-1-ylmethylene]-N-methylmethanaminium hexafluorophosphate N-oxide (35.0 g, 92.1 mmol), 6-fluoropyridine-2-sulfonamide (16.5 g, 93.8 mmol) and ethyldiisopropylamine (36 mL) in N,N-dimethylformamide (400 mL) at 5 C. The resulted mixture was stirred at room temperature overnight before it was quenched with 1 N HCl (150 mL). The mixture was diluted with water (450 mL) and the resultant solids were collected by filtration and washed with water (500 mL), methanol (200 mL) and Et2O (400 mL). The solid was purified by silica gel column chromatography (0-4% methanol/CH2Cl2) to afford 6-chloro-N-[(6-fluoro-2-pyridyl)sulfonyl]-2-(2,4,6-trimethylphenoxy)pyridine-3-carboxamide as a white solid (22.2 g, 60%). NMR (CDCl3, 250 MHz) delta 8.36 (dd, J=15.7, 7.5 Hz, 1H), 8.14 (d, J=7.5 Hz, 1H), 8.08 (d, J=8.0 Hz, 1H), 7.58 (d, J=8.2 Hz, 1H), 7.29 (d, J=7.8 Hz, 1H), 6.91 (s, 2H), 2.25 (s, 3H), 1.94 (s, 6H).

According to the analysis of related databases, 124433-70-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; Miller, Mark Thomas; Anderson, Corey; Arumugam, Vijayalaksmi; Bear, Brian Richard; Binch, Hayley Marie; Clemens, Jeremy J.; Cleveland, Thomas; Conroy, Erica; Coon, Timothy Richard; Frieman, Bryan A.; Grootenhuis, Peter Diederik Jan; Gross, Raymond Stanley; Hadida-Ruah, Sara Sabina; Haripada, Khatuya; Joshi, Pramod Virupax; Krenitsky, Paul John; Lin, Chun-Chieh; Marelius, Gulin Erdgogan; Melillo, Vito; McCartney, Jason; Nicholls, Georgia McGaughey; Pierre, Fabrice Jean Denis; Silina, Alina; Termin, Andreas P.; Uy, Johnny; Zhou, Jinglan; (590 pag.)US2016/95858; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 105596-61-0, 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 105596-61-0, name is Ethyl 2-methoxyisonicotinate. This compound has unique chemical properties. The synthetic route is as follows.

A solution of ethyl 2-methoxy-pyridine-4-carboxylate (0.93 g, 5 mmol) in ether (5 ml) was added to lithium aluminium hydride (0.3 g, 8 mmol) in ether (10 ml) cooled to 5 C. and the mixture stirred for 2 hours. Water was added, the mixture was filtered through diatomaceous earth and the pad was washed through with ethyl acetate. The filtrate was extracted with ethyl acetate and the combined extracts were washed with brine, dried (MgSO4) and the solvent removed by evaporation to give 4-hydroxymethyl-2-methoxypyridine (0.64 g, 89%) as a yellow oil. 1 H NMR Spectrum: (CDCl3) 3.86(s, 3H); 4.62(s, 2H); 6.65(s, 1H); 6.76(d, 1H); 8.05(d, 1H) MS – ESI: 140 [MH]+

According to the analysis of related databases, 105596-61-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Zeneca Limited; Zeneca Pharma S.A.,; US5962458; (1999); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1122-71-0, 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. 1122-71-0, name is 6-Methyl-2-pyridinemethanol. A new synthetic method of this compound is introduced below.

Example 45 2-[(6-Methylpyridin-2-yl)methoxy]-4-(2-methylpyrimi din-5-yl)-6,7-dihydro-5H-cyclopenta[b]pyridine hydrochloride To 2-chloro-4-(2-methylpyrimidin-5-yl)-6,7-dihydro-5H-cyclopenta[b]pyridine (100 mg), (6-methylpyridin-2-yl)methanol (52 mg), t-Bu-X-Phos (55 mg), and cesium carbonate (398 mg) and Pd2 (dba)3¡¤CHCl3 (34 mg) was added toluene (2.2 mL), and the mixture was degassed, then stirred under Ar atmosphere at 100C for 6 hours. After the reaction mixture was allowed to return to room temperature, diluted with ethyl acetate, filtered through Celite, and the filtrate was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography to give 2-[(6-methylpyridin-2-yl)methoxy]-4-(2-methylpyrimi din-5-yl)-6,7-dihydro-5H-cyclopenta[b]pyridine (49 mg). Theresulting compound was dissolved in ethyl acetate (2 mL) and 1N HCl/Et2O solution (0.147 mL) was added, then themixture was stirred under ice water cooling for 3 hours. The resulting precipitate was collected by filtration to give thetitle compound (43 mg) as a white powder.[MS (ESI) m/z 333.4 (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,1122-71-0, its application will become more common.

Reference:
Patent; Nippon Shinyaku Co., Ltd.; TSUJI, Takashi; SHIRAI, Masaaki; EP2891656; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 106877-33-2, 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.106877-33-2, name is 5-Amino-2-(trifluoromethyl)pyridine, molecular formula is C6H5F3N2, molecular weight is 162.11, as common compound, the synthetic route is as follows.

A solution of sodium nitrite (213 mg, 3.08 mmol) in water (620 pL) was slowly added to a suspension of 6-(trifluoromethyl)pyridine-3-amine (500 mg, 3.08 mmol) in cone. HC1 (525 pL) and ice (620 mg) at 0 C. After five minutes of stirring at 0 C a solution of potassium ethyl xanthate (593 mg, 3.70 mmol) in EtOH/water (1/1, 2 mL) was added and the resulting yellow slurry was heated at 50-55 C for 30 minutes. Then the reaction mixture was allowed to cool to rt and was then diluted with water (10 mL) and EtiO (10 mL). The phases were separated and the water phase was extracted with EtiO (2x 10 mL). The combined organics were washed with brine (10 mL) and dried (MgSCri). After filtration and evaporation, the crude material (659 mg) was dissolved in EtOH (8 mL) and potassium hydroxide (735 mg) was added. The resulting mixture was heated at 90 C for two hours and was then allowed to cool to rt. The reaction mixture was then filtered and the filtrate was acidified with citric acid, before being diluted with EtiO. The organic phase was washed with brine and dried (MgSCri). After filtration and evaporation of the solvent, the crude was dried under vacuum at 45 C over night. The title compound (150 mg) was obtained as a yellow crude solid, which was not purified further but used directly in the next step. ‘H NMR (CDCb) S 8.80 (br s, 1H) 7.99 (br d, =8.4 Hz, 1H9 7.66 (br d, =8.4 Hz).

The chemical industry reduces the impact on the environment during synthesis 106877-33-2, I believe this compound will play a more active role in future production and life.

Reference:
Patent; RESPIRATORIUS AB (PUBL); DALENCE, Maria; JOHANSSON, Martin; THORNQVIST OLTNER, Viveca; TOFTERED, Joergen; WENSBO, Davis; (49 pag.)WO2020/9653; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 65189-15-3, 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. 65189-15-3, name is 5,6-Dichloronicotinonitrile. A new synthetic method of this compound is introduced below.

Example 3 5-Chloro-2-methylthio-3-pyridinecarbonitrile STR11 5,6-Dichloro-3-pyridinecarbonitrile (1.73 g, 0.01 mol) was dissolved with stirring in dimethyl sulphoxide (25 mL) and sodium methanethiolate (0.77 g, 0.011 mol) added. The reaction mixture was stirred at room temperature for two hours and poured onto ice (100 g). The mixture was extracted with dichloromethane (50 mL), and the organic extract washed with water (100 mL), and brine, and dried over anhydrous sodium sulphate. Evaporation of the solvent under reduced pressure and recrystallisation of the residue from ethyl acetate:hexane gave the desired product (1.3 g, 71%) as a cream solid, MP 147-9 C.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,65189-15-3, 5,6-Dichloronicotinonitrile, and friends who are interested can also refer to it.

Reference:
Patent; Kirby; Neil V.; Morrison; Irene M.; Canada; Emily J.; Pieczko; Mary E.; Gustafson; Gary D.; Cooper; David H.; Adamski; Jenifer L.; Mathieson; John T.; Galka; Christopher S.; US6133294; (2000); A;,
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. 73027-79-9, name is 4,6-Dichloronicotinic acid. This compound has unique chemical properties. The synthetic route is as follows. SDS of cas: 73027-79-9

[00240] Step A: 6-Dichloro-4-(2-fluoro-4-iodophenylamino)nicotinic acid:[00241] To a solution of 2-fluoro-4-iodoaniline (11.3 g, 50.3 mmol) in 85 ml anhydrous THF is added LiHMDS (83 ml, 83 mmol, 1M/THF) over a period of 30 min at -78C. It is stirred for another 30 min, then a solution of methyl 4,6-dichloronicotinate (step B, example 9) (5.00 g, 26.2 mmol) in 85 ml THF is added dropwise. After complete addition the mixture is gradually allowed to warm to room temperature and stirred for another 18 hrs. It is quenched with H2O, then 1N HCl is added to (pH = 1) followed by brine. It is extracted using THF and dried with Na2SO4. The solvents are removed and the crude solid is suspended in300 ml of EtOAc. The suspension is heated with stirring at the reflux temperature for 5 min. It is cooled to room temperature and the precipitate is filtered and washed with EtOAc and dried at 50C for 5 h in oil pump vacuo.

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, 73027-79-9, 4,6-Dichloronicotinic acid.

Reference:
Patent; ARDEA BIOSCIENCES, INC.; WO2008/89459; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 17874-79-2, 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. 17874-79-2, name is 5-(Methoxycarbonyl)picolinic acid, molecular formula is C8H7NO4, 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.

10314] Dimethyl-2,5-pyridinedicarboxylate (960 mg, 4.9mmoles) and CaC12 (2.198 g, 19.7 mmoles) were added to a dried flask. THF (11 mE) and EtOH (12 mE) were added, and the resulting suspension was stirred on ice for 30 minutes. NaI3H4 (465 mg, 12.3 mmoles) was added portion wise with stirring. The reaction was allowed to come to room temperature overnight. Afier 18 h, the reaction was quenched by the dropwise addition of an aqueous solution of NH4C1 (saturated aqueous NH4C1 [20 mE] plus H20 [40 mE]) while stirring on ice. The aqueous layer was extracted with DCM (4×30 mE) and the combined organics were dried over Na2SO4(s) and concentrated under reduced pressure to afford the crude alcohol (678 mg) as a pale yellow solid. The crude alcohol was dissolved in dry DCM (45 mE), after which Dess-Martin periodinane (2.6 g, 6.1 mmoles) was added portion wise while stirring on ice. After 6 h, the reaction was quenched by the dropwise addition of a solution of 5% Na2S2O3 in half saturated NaHCO3 (80 mE). The aqueous layer was extracted with DCM (3×40 mE). The combined organics were dried over Na2SO4(s) and concentrated under reduced pressure to afford the title compound (504 mg, 62%) as a pale yellow solid. ?H NMR (400 MHz, CDC13) oe 10.16 (s, 1H), 9.38 (dd, J=0.5, 2.0 Hz, 1H), 8.49 (dd, J=2.0, 8.0 Hz, 1H), 8.05 (dd, J=0.5, 8.0 Hz, 1H), 4.02 (s, 1H); ?3C NMR (100 MHz, CDC13) oe 192.6, 164.8, 154.9, 151.2, 138.3, 121.1, 52.9; HRMS (El) mlz 165.0415 [calc?d for C8H7N03 (M) 165.042 1]

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 17874-79-2, 5-(Methoxycarbonyl)picolinic acid.

Reference:
Patent; WISCONSIN ALUMNI RESEARCH FOUNDATION; RAINES, Ronald T.; Vasta, James; (50 pag.)US2016/280701; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem