Category: pyridine-derivatives

Related Products of 885168-20-7, 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. 885168-20-7, name is 2-Bromo-5-fluoro-4-methylpyridine, molecular formula is C6H5BrFN, 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.

To a mixture of 2-bromo-5-fluoro-4-methylpyridine (25.0 g, 131.5 mmol), tris(dibenzylideneacetone)dipalladium(0) (3.0 g, 3.3 mmol) and 4,5- bis(diphenylphosphino)-9,9-dimethylxanthene (3.8 g, 6.6 mmol) in anhydrous 1 ,4- dioxane (260 mL) was added A/./V-diisopropylethylamine (34.4 mL, 197 mmol) and benzyl mercaptan (14.6 mL, 125 mmol). The reaction mixture was carefully degassed with nitrogen and then heated at 100 C for 16 hours. After cooling to ambient temperature, the reaction mixture was concentrated under reduced pressure. After addition of water (50 mL) to the residue, the mixture was extracted with ethyl acetate (2 x 100 mL). The combined organic layers were washed with brine (50 mL), dried over anhydrous sodium sulfate, and filtered. Concentration of the filtrate under reduced pressure and purification of the residue by column chromatography, eluting with a gradient of 0 to 30% of ethyl acetate in heptane, afforded the title compound as colorless oil (28.0 g, 91% yield): 1H NMR (300MHz, DMSO-cfe) £8.38 (d, J = 1.5 Hz, 1 H), 7.38 (dd, J = 8.1 , 1.5 Hz, 2H), 7.27-7.22 (m, 4H), 4.38 (s, 2H), 2.22 (d, J = 0.9 Hz, 3H); MS (ES+) m/z 234.2 (M + 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 885168-20-7, 2-Bromo-5-fluoro-4-methylpyridine.

Reference:
Patent; XENON PHARMACEUTICALS INC.; FOCKEN, Thilo; ANDREZ, Jean-Christophe; BURFORD, Kristen Nicole; DEHNHARDT, Christoph Martin; GRIMWOOD, Michael Edward; JIA, Qi; LOFSTRAND, Verner Alexander; WILSON, Michael Scott; ZENOVA, Alla Yurevna; WESOLOWSKI, Steven Sigmund; SUN, Shaoyi; (205 pag.)WO2020/47323; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1193-71-1, 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 1193-71-1 as follows.

[00112] To the solution of 4-(5-ethyl-2-(5-methylpyrazin-2-yl)thiazol-4-yl)benzoate (75 mg, 0.22 mmol) in toluene (4 mL) was added 4,6-dimethylpyridin-3-amine (53 mg, 0.42 mmol) and AlMe3 (2M solution in toluene, 0.21 mL, 0.42 mmol). The reaction was heated in microwave at 110 C for 15 min before it was diluted with EtOAc (15 mL) and washed with IN NaOH (25 mL chi 2). The organic phase was dried over magnesium sulfate, filtered, and concentrated. Column chromatography gave compound 5 in 81% yield. [00113] NMR (400 MHz, CDCls) delta 9.34 (d, / = 1.5 Hz, 1H), 8.75 (s, 1H), 8.43 (d, / = 1.5 Hz, 1H), 8.04 – 7.99 (m, 2H), 7.89 – 7.83 (m, 2H), 7.73 (s, 1H), 7.08 (s, 1H), 3.08 (q, / = 7.5 Hz, 2H), 2.64 (s, 3H), 2.54 (s, 3H), 2.32 (s, 3H), 1.43 (t, / = 7.4 Hz, 3H). ESMS cacld (C24H23N5OS): 429.2; found: 430.3 (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,1193-71-1, its application will become more common.

Reference:
Patent; SYNTA PHARMACEUTICALS CORP.; CHEN, Shoujun; ZHANG, Junyi; JIANG, Jun; KOWALCZYK-PRZEWLOKA, Teresa; XIA, Zhiqiang; ZHANG, Shijie; WO2013/63385; (2013); 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. 116355-18-1, name is 6-Bromo-7-methylimidazo[1,2-a]pyridine, molecular formula is C8H7BrN2, 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. Application In Synthesis of 6-Bromo-7-methylimidazo[1,2-a]pyridine

(2) 6-bromo-3-iodo-7-methylimidazo[l,2-a]pyridine.; To a 15O mL round bottomed flask was added 6-bromo-7-methylimidazo[l,2-a]pyridine (4.300 g, 20.37 mmol), sodium acetate anhydrous (2.95 mL, 55.0 mmol) and MeOH (60 mL). The resulting mixture was cooled to 0 0C followed by adding iodine (5.7 g, 22.41 mmol). After the addition, ice bath was removed. After 20 h, the solid in the reaction mixture was collected by filtration. The solid was washed with MeOH affording the desired product as a light grey solid (5.1 g). MS (ESI pos. ion) m/z: 336.7. Calcd exact mass for C8H6BrIN2: 335.9. 1H NMR (300 MHz, CHLOROFORM-J) delta ppm 2.50 (s, 3 H) 7.49 (s, 1 H) 7.64 (s, 1 H) 8.30 (s, 1 H).

With the rapid development of chemical substances, we look forward to future research findings about 116355-18-1.

Reference:
Patent; AMGEN INC.; BO, Yunxin, Y.; LIU, Longbin; NISHIMURA, Nobuko; NORMAN, Mark, H.; SIEGMUND, Aaron, C.; TAMAYO, Nuria, A.; YANG, Kevin; WO2010/108074; (2010); A2;,
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 1020253-14-8, name is 6-Chloro-5-fluoronicotinonitrile. This compound has unique chemical properties. The synthetic route is as follows. Formula: C6H2ClFN2

Step 1: 6-(3-(4-((tert-butyldimethylsilyl)oxy)-2-chlorophenyl)-3-hydroxyazetidin-1-yl)-5-fluoronicotinonitrile (0270) A mixture of 26 3-(4-((tert-butyldimethylsilyl)oxy)-2-chlorophenyl)azetidin-3-ol hydrochloride (1c, 0.40 g, 1.1 mmol), 84 2-chloro-3-fluoropyridine-5-carbonitrile (0.18 g, 1.1 mmol), and 23 potassium carbonate (0.43 g, 3.1 mmol) in 8 DMF (2.5 mL) was heated at 65 C. for 30 minutes. The mixture was purified by flash chromatography (silica gel) to provide the desired 130 material. LCMS-ESI+(m/z): [M+H]+ calcd for C21H26ClFN3O2Si: 434.1; found: 434.0.

With the rapid development of chemical substances, we look forward to future research findings about 1020253-14-8.

Reference:
Patent; Gilead Sciences, Inc.; Blomgren, Peter A.; Currie, Kevin S.; Farand, Julie; Gege, Christian; Kropf, Jeffrey E.; Xu, Jianjun; (35 pag.)US2017/355693; (2017); 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. 95652-80-5, name is 2-Chloro-6-methoxynicotinaldehyde, molecular formula is C7H6ClNO2, 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. name: 2-Chloro-6-methoxynicotinaldehyde

Palladium (II) acetate (0.08 g, 0.36 mmol) , caesium carbonate (2.23 g, 6.83 mmol), 2-di-tert-butylphosphino-2 ‘ , 4 ‘ , 6 ‘ – triisopropylbiphenyl (t-Butyl XPhos) (0.290 g, 0.68 mmol), compound 6 (0.59 g, 3.41 mmol), and 4 (0.88 g, 4.44 mmol) and toluene (30 mL) were combined and purged by a stream of argon for 3 minutes. The reaction was sealed and heated at 80 C for 4h. The mixture was filtered through a pad of Celite. The filtrate was concentrated under reduced pressure. The product was purified by flash chromatography on silica gel using 0-60% ethyl acetate in hexane. The product was recrystallized from diethyl ether (488 mg, 35%). mp : 132.0-133.0 C; 1H NMR (600MHz, CDC13) delta [ppm] : 10.22 (d, J=0.8 Hz, 1H) , 8.06 (d, J=8.4 Hz, 1H) , 7.44-7.41 (m, 3H) , 7.37-7.34 (m, 1H) , 7.32-7.30 (m, 2H) , 7.28 (d, J=7.5 Hz, 1H) , 7.26 (m, 1H) , 6.45 (dd, Jl=8.4 Hz, J2=0.8 Hz, 1H) , 5.52 (s, 2H) , 4.08 (3H), 2.28 (s, 3H) ; 13C NMR (151 MHz, DMSO-d6) delta [ppm] : 187.8, 166.6, 165.2, 143.2, 142.0, 140.5, 135.0, 134.8, 130.5, 129.5, 128.7, 128.3, 127.1, 125.7, 112.5, 103.9, 67.8, 54.1, 16.5; IR V (ATR cm-1): 3063, 2961, 2870, 1671, 1591, 1460, 1330, 1277; HRMS (ESI-TOF) Calcd for C21H19N03Na [M+Na]+ : 356.1263; found [M+Na]+: 356.1256.

With the rapid development of chemical substances, we look forward to future research findings about 95652-80-5.

Reference:
Patent; RIJKSUNIVERSITEIT GRONINGEN; DOeMLING, Alexander; (85 pag.)WO2017/118762; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 75291-85-9, 5-Bromo-2-chloronicotinamide, 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, 75291-85-9, blongs to pyridine-derivatives compound. SDS of cas: 75291-85-9

Preparation 133(35,45)-4-[(5-bromo-3-carbamoylpyridin-2-yl)oxyl-3-fluoropiperidine- 1 -carboxylate To a solution of tert-butyl (3S,4S)-3-fluoro-4-hydroxypiperidine- 1 -carboxylate (WO 20131011402 Al, 605 mg, 2.76 mmol) in DMSO (4 mL) was added potassium tert-butoxide (464 mg, 4.14 mmol) and the mixture stirred at room temperature for 30 minutes. 5-bromo-2- chloronicotinamide (Preparation 177, 650 mg, 2.76 mmol) was added and the reaction stirred at room temperature for 16 hours. The reaction was quenched by the addition of water andextracted into EtOAc. The organic layer was collected, washed with water, dried over sodiumsulphate and concentrated in vacuo. The residue was purified using silica gel columnchromatography eluting with 30% EtOAc in heptanes to afford the title compound (800 mg,69%).1H NMR (400 MHz, DMSO-d6): O ppm 1.41 (5, 9H), 1.74 (m, 1H), 2.06 (m, 1H), 3.28-3.83 (m,4H), 4.80-4.93 (m, 1H), 5.41 (m, 1H), 7.64 (br 5, 1H), 7.68-7.82 (m, 2H), 8.21 (m, 1H), 8.42 (5,1H).MS mlz 318 [M79Br-Boc+H]

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,75291-85-9, its application will become more common.

Reference:
Patent; PFIZER LIMITED; SKERRATT, Sarah Elizabeth; BAGAL, Sharanjeet Kaur; SWAIN, Nigel Alan; OMOTO, Kiyoyuki; ANDREWS, Mark David; WO2015/92610; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 13626-17-0, 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 13626-17-0 as follows.

Intermediate 24: 2-(benzeuesulfonyl)-2-(5-bromo-4-chloropyridin-3-yl)acetonitrile To a stirred and nitrogen degassed solution of 2-{benzenesulfonyflacetonitrile (CM 7605-25-9; 7.64 g, 42.20 mmol) in anhydrous DME (100 mL) was added sodium hydride (3.83 g, 96 mmol, 6o% dispersion in oil) at o C. The mixture was stirred at oC for 5 mm and then at it for 15 mm. This mixture was added to a previously nitrogen degassed solution of 3,5-dibromo-4-chloropyfldane (CM 13626-17-0; 10.40 g, 38.30 mmol), tetrakis(triphenylphosphane) palladium (i.ii g, 958 jimol) in anhydrous DME (100 mL). The reaction mixture was heated at reflux for 16 h. The reaction mixture was partitioned between EtOAc and water. The organic phase was washed with brine, dried (MgSO4) and concentrated in vacuo. The crude product was purified by column chromatography (Ci8-silica, o-8o% acetonitrile / water (with o.i% ammonia)) to affordthe title compound. -?H NMR (400 MHz, DMSO-d6) 6 ppm 7.37 7.58 (m, 3 H) 7.67 – 7.83 (m, 3 H) 8.13 – 8.29 (m, 1 H) 8.31 – 8.44 (m, 1 H)MS ES: 372

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,13626-17-0, its application will become more common.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; TAKEDA CAMBRIDGE LTD; BARKER, Gregory; DAVENPORT, Richard; DOWNHAM, Robert; FARNABY, William; GOLDBY, Anne; HANNAH, Duncan; HARRISON, David; WILLEMS, Henriette; (390 pag.)WO2015/198045; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1352625-30-9, 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.1352625-30-9, name is 3-Bromo-6-fluoropyrazolo[1,5-a]pyridine, molecular formula is C7H4BrFN2, molecular weight is 215.02, as common compound, the synthetic route is as follows.

c) 6-Fluoro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazolo[1,5-a]pyridine A mixture of 3-bromo-6-fluoropyrazolo[1,5-a]pyridine (Preparation 103b, 0.300 g, 1.4 mmol), potassium acetate (0.492 g, 5.0 mmol) and bis(pinacolato)diboron (2.77 g, 10.9 mmol) in 1,4-dioxane (5 mL) contained in a Schlenck vessel was submitted to three vacuum-argon cycles and tetrakis(triphenylphosphine)palladium(0) (0.380 g, 0.33 mmol) was then added. The mixture was further submitted to three vacuum-argon cycles, sealed and then was stirred and heated to 100 C. After 20 hours, the reaction mixture was cooled, evaporated and then taken up in pentane and filtered through diatomaceous earth (Celite) and the filter cake was washed with a mixture of ethyl acetate/ether (3:2). The combined filtrate and washings were evaporated and the residue was purified by reverse phase chromatography (C-18 silica from Waters, water/acetonitrile/methanol as eluents [0.1% v/v formic acid buffered] 0% to 100%) to give the title compound (0.130 g, 36%) as a yellow solid. LRMS (m/z): 263 (M+1)+.1H NMR (300 MHz, CDCl3) delta ppm (two sets of peaks are seen in the NMR due to the presence of both the boronate and boronic acid): NMR of boronate: 1.21 (s, 12H), 7.56 (m, 1H), 8.02 (m, 1H), 8.36 (s, 1H), 9.16 (m, 1H).; PREPARATION 104 2-(6-Fluoropyrazolo[1,5-a]pyridin-3-yl)-9-(tetrahydro-2H-pyran-4-yl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-purin-8(9H)-one [Show Image] A mixture of 2-chloro-9-(tetrahydro-2H-pyran-4-yl)-7-{[2-(trimethylsilyl)ethoxy]methyl}-7,9-dihydro-8H-purin-8-one (Preparation 3, 0.150 g, 0.39 mmol), 6-fluoro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazolo[1,5-a]pyridine (Preparation 103, 0.183 g, 0.70 mmol) and potassium acetate (0.134 g, 1.37 mmol) in 1,4-dioxane (5 mL) and water (1.5 mL) contained in a Schlenck vessel was submitted to three vacuum-argon cycles and tetrakis(triphenylphosphine)palladium(0) (0.040 g, 0.03 mmol) was then added. The mixture was further submitted to three vacuum-argon cycles, sealed and then was stirred and heated under microwave irradiation (“Initiator sixty” from Biotage) at 120 C under an atmosphere of argon. After 40 minutes, further 2-chloro-9-(tetrahydro-2H-pyran-4-yl)-7-{[2-(trimethylsilyl)ethoxy]methyl}-7,9-dihydro-8H-purin-8-one (0.060 g, 0.16 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.020 g, 0.017 mmol) were added and heating was continued for 90 minutes. The reaction mixture was evaporated and then was partitioned between ethyl acetate and water and the organic layer was dried (MgSO4) and concentrated. The residue was purified by flash chromatography (3:1 to 2:1 hexanes/ethyl acetate) to give the title compound (0.096 g, 50%) as pale yellow solid. LRMS (m/z): 485 (M+1)+.1H NMR (300 MHz, CDCl3) delta ppm 0.06 (s, 9H), 1.00 (t, 2H), 1.80 (m, 2H), 2.91 (dq, 2H), 3.49 (s, 2H), 3.68 (m, 2H), 4.22 (m, 2H), 4.63 (m, 1H), 5.25 (s, 2H), 7.38 (t, 1H), 8.40 (s, 1H), 8.52 (m, 1H), 8.65 (dd, 1H), 8.78 (s, 1H).

Statistics shows that 1352625-30-9 is playing an increasingly important role. we look forward to future research findings about 3-Bromo-6-fluoropyrazolo[1,5-a]pyridine.

Reference:
Patent; Almirall, S.A.; EP2397482; (2011); 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. 53636-70-7, name is 6-Methyl-2,3-pyridinedicarboxylic acid, the common compound, a new synthetic route is introduced below. HPLC of Formula: C8H7NO4

6-methylpyridine-2,3-dicarboxylic acid (5.50 g, 30.36 mmol) was dissolved in Acetic anhydride (14.3 ml_) and the mixture heated at 100 C under nitrogen for 5 hours. Volatiles were removed under vacuum to give 2-methyl-5H,7H-furo[3,4-b]pyridine-5,7- dione (Int. a, 4.97 g).

The synthetic route of 53636-70-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CHRONOS THERAPEUTICS LIMITED; MICHELI, Fabrizio; BERTANI, Barbara; GIBSON, Karl Richard; DI FABIO, Romano; RAVEGLIA, Luca; ZANALETTI, Riccardo; CREMONESI, Susanna; POZZAN, Alfonso; SEMERARO, Teresa; TARSI, Luca; LUKER, Timothy Jon; (275 pag.)WO2019/43407; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 109306-86-7 ,Some common heterocyclic compound, 109306-86-7, molecular formula is C11H8BrN, 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.

A solution of 117.5 mg of 2- (2-bromophenyl) pyridine (0.5 mmol)And 70.15 mg of potassium methoxide (1 mmol) were dissolved in 1 mL of deuterated acetonitrile, and 200 muL of hexamethyldisilane (1 mmol) was added dropwise to the mixture, and the mixture was stirred at room temperature for 12 h. After completion of the reaction, 10 mL of water was quenched and extracted with 30 mL of ether three times. The organic phase was collected and the solvent was removed under reduced pressure. The eluent was petroleum ether: ethyl acetate = 10: 1 (v / v) to give 68 mg of 2- (2-deuterated) pyridine (pale yellow liquid in 87% 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. 109306-86-7, 2-(2-Bromophenyl)pyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Wuhan University; Liu Wenbo; Wang Xin; Zhong Dayou; (23 pag.)CN106928117; (2017); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem