Category: pyridine-derivatives

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. 30766-11-1, name is 5-Bromopicolinic acid, the common compound, a new synthetic route is introduced below. category: pyridine-derivatives

To a cooled solution (0 C.) of commercially available 5-bromopyridine-2-carboxylic acid (1 g, 5 mmol) in THF (20 mL) and DMF (1 mL) was dropwise added thionylchloride (0.54 mL, 7 mmol), removed the ice bath and stirred at 23 C. for 1 h. Cooled to 0 C., dropwise added of an excess of 25% aqueous ammoniumhydroxid solution (3.7 mL, 50 mmol) and stirred at 0 C. for 30 min. Filtered the precipitated solid off and dissolved in AcOEt, washed the AcOEt-layer once with brine, dried over Na2SO4. Removal of the solvent in vacuum left a white solid, which was triturated with heptane and dried in HV to give the title compound as a white solid (500 mg, 50%). MS (ISP) 201.1 [(M+H)+], 203.1 [(M+2+H)+].

The synthetic route of 30766-11-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; McArthur, Silvia Gatti; Goetschi, Erwin; Palmer, Wylie Solang; Wichmann, Juergen; Woltering, Thomas Johannes; US2006/217387; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 3510-66-5, 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. 3510-66-5, name is 2-Bromo-5-methylpyridine, molecular formula is C6H6BrN, 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 6-bromo-3-methylpyridine to methanol, reduce the temperature to 20-30 C in an ice-water bath, and slowly drop the methanol solution of sodium methoxide into the reaction system, keeping the internal temperature below 40 C. , Heated to reflux, reacted at 70-80 C for 12h, the reaction equation is as follows:The temperature of the reaction solution was reduced to 45-50 C, and concentrated to half the volume under reduced pressure; the temperature was reduced to 25-30 C, and water was added. The amount of water added was 5.5-8.0 times that of 6-bromo-3-methylpyridine, and stirred for 10min. ; The treatment solution was extracted three times with dichloromethane. The amount of dichloromethane was 10.0-12.0 times that of 6-bromo-3-methylpyridine. The organic phases were combined and washed once with water. -Methoxy-3-methylpyridine, yield 94.3%, GC purity 99.1%.Among them, the amount of methanol is 4.5-5.0 times that of 6-bromo-3-methylpyridine.The molar ratio of 6-bromo-3-methylpyridine to sodium methoxide is 1: 1.4.

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 3510-66-5, 2-Bromo-5-methylpyridine.

Reference:
Patent; Nanjing Habo Pharmaceutical Technology Co., Ltd.; Zhao Xiaolin; Cui Jiayi; Wang Jinzhu; Zhao Bing; Ai Yangbao; (10 pag.)CN110878043; (2020); A;,
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. 16665-38-6, name is (4-Methoxypyridin-2-yl)methanol. A new synthetic method of this compound is introduced below., SDS of cas: 16665-38-6

Synthesis of 2-azidomethyl-4-methoxypyridine.[0298] 2-Hydroxymethyl-4-methoxypyridine (278 mg, 2.0 mmol) was dissolved in tetrahydrofuran (15 mL) in a 50 mL round-bottomed flask under argon. The flask was cooled to 0-5 C with an ice/water bath for 10 minutes at which time, powdered OH (157 mg, 2.8 mmol) was added followed by /?erra-toluenesulfonyl chloride (pTsCl). The reaction was stirred for 12 hours, at which time diethyl ether (30 mL) was added. The mixture was transferred to a separatory funnel, and a saturated solution of NaHCC>3 (40 mL) was added. The organic layer was dried with MgSC>4, filtered, and concentrated to a residue, which was chromatographed on a silica gel column with a 10% to 50% gradient of ethyl acetate/hexanes. Rf = 0.69 (ethyl acetate, 254 nm UV). This material was then dissolved in N,N-dimethylformamide (5 mL), and sodium azide (266mg, 4.09 mmol) was added and the reaction was stirred at ambient temperature for 16 hours, at which time the reaction mixture was diluted with diethyl ether (30 mL) and washed with a saturated solution of NaHCC>3 (3 x 30 mL), then with brine (25 mL), dried with MgS04, filtered and concentrated in vacuo. The resulting residue was chromatographed over silica gel with a 15% to 50% gradient of ethyl acetate/hexanes to furnish 100 mg (30% yield) of this compound as a light yellow oil. Rf = 0.68 (ethyl acetate, 254 nm UV). NMR (400MHz, CDCh): 8.34 (d, J= 5.6 Hz, 1H,), 6.81 (d, J= 2.4 Hz 1 H), 4.39 (s, 2H), 3.81 (s,

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, 16665-38-6, (4-Methoxypyridin-2-yl)methanol.

Reference:
Patent; LIFE TECHNOLOGIES CORPORATION; GEE, Kyle; SINGH, Upinder; GRECIAN, Scott; WO2012/121973; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 73583-37-6, Adding some certain compound to certain chemical reactions, such as: 73583-37-6, name is 4-Bromo-2-chloropyridine,molecular formula is C5H3BrClN, 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 73583-37-6.

(1) Tert-butyl 4-(2-chloropyridin-4-yl)piperazine-1-carboxylate A mixture of 4-bromo-2-chloropyridine (3.87 ml, 34.9 mmol), tert-butyl piperazine-1-carboxylate (5.0 g, 26.9 mmol), trisdibenzylideneacetone dipalladium (492 mg, 0.537 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethyxanthene (932 mg, 1.61 mmol), sodium tert-butoxide (3.87 g, 40.3 mmol) and toluene (270 ml) was stirred at 100 C. for 6 hours. The reaction was poured into water and extracted with ethyl acetate. The extract was washed with water, dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate_hexane=1:1) to obtain the title compound (5.62 g, 70%) as a solid. 1H NMR (CDCl3) delta: 1.49 (9H, s), 3.30-3.37 (4H, m), 3.52-3.60 (4H, m), 6.57 (1H, dd, J=6.1, 2.4 Hz), 6.65 (1H, d, J=2.4 Hz), 8.04 (1H, d, J=6.1 Hz). (1) Tert-butyl 4-(2-chloropyridin-4-yl)piperazine-1-carboxylate; To a solution of 4-bromo-2-chloropyridine (15.0 g, 77.3 mmol) and tert-butyl piperazine-1-carboxylate (18.0 g, 77.3 mmol) in anhydrous toluene (400 ml) was added sodium tert-butoxide (11.0 g, 116 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethyxanthene (1.34 g, 2.32 mmol) and trisdibenzylideneacetone dipalladium (445 mg, 0.77 mmol) under nitrogen atmosphere, and the reaction was deaerated and heated under reflux for 14 hours. The reaction was distilled off under reduced pressure and to the residue was added ethyl acetate and water followed by extracted. The extract was washed with saturated brine and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (petroleum ether:ethyl acetate=5:1) to obtain the title compound (16.0 g, 70%) as a solid.1H NMR (CDCl3) delta: 1.45 (9H, s), 3.30-3.32 (4H, m), 3.52-3.54 (4H, m), 6.52-6.55 (1H, m), 6.01 (1H, s), 7.97-8.04 (1H, m).

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. 73583-37-6, 4-Bromo-2-chloropyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; US2009/163508; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 934-60-1 , The common heterocyclic compound, 934-60-1, name is 6-Methyl-2-pyridinecarboxylic acid, molecular formula is C7H7NO2, 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.

[0349j Methyl 6-methylpicolinate 3.41: To a 250-mL round-bottomed flask was added 6-methylpicolinic acid (TCI, 5.35 g, 39.0 mmol) and MeOH (100 mL). Concentrated sulfuric acid (3.12 mL, 58.5 mmol) was added dropwise. The reaction was heated at reflux for 48 h. After cooling to RT, most of the solvent was evaporated. The resulting residue was diluted with saturated aqueous NaHCO3 and extracted with DCM (2 x 100 mL). The organic extracts were dried over MgSO4, filtered and concentrated in vacuo to give 6-methylpicolinate (5.33 g, 35.3 mmol, 90% yield) as a light-yellow oil. MS (M–H) 152.0.

The synthetic route of 934-60-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AMGEN INC.; CHEN, Ning; CHEN, Xiaoqi; CHEN, Yinhong; CHENG, Alan C.; CONNORS, Richard V.; DEIGNAN, Jeffrey; DRANSFIELD, Paul John; DU, Xiaohui; FU, Zice; HEATH, Julie Anne; HORNE, Daniel B.; HOUZE, Jonathan; KALLER, Matthew R.; KHAKOO, Aarif Yusuf; KOPECKY, David John; LAI, Su-Jen; MA, Zhihua; MCGEE, Lawrence R.; MEDINA, Julio C.; MIHALIC, Jeffrey T.; NISHIMURA, Nobuko; OLSON, Steven H.; PATTAROPONG, Vatee; SWAMINATH, Gayathri; WANG, Xiaodong; YANG, Kevin; YEH, Wen-Chen; DEBENEDETTO, Mikkel V.; FARRELL, Robert P.; HEDLEY, Simon J.; JUDD, Ted C.; KAYSER, Frank; (1266 pag.)WO2016/187308; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 876919-08-3, 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. 876919-08-3, name is Methyl 3-fluoroisonicotinate, molecular formula is C7H6FNO2, 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 solution ofPreparation 69A (100 mg, 0.42 mmol) in DMA (5 mL) wasadded methyl3-fluoroisonicotinate (65 mg, 0.42 mmol) at rt. The reaction was stirred at170 oc for 1 h in a microwave. The reaction mixture was diluted with water extracted with EtOAc. Organics were washed with brine, dried (Na2 S04), and concentrated. Purification by silica gel chromatography (5:1 PE/EtOAc) gave 50 mg (32%) of the titlecompound as a yellow solid. 1H NMR (300 MHz, CDCh): 8 3.92 (3H, s), 4.27-4.28 (2H,m), 4.81-4.82 (2H, m), 5.78-5.80 (1H, m), 7.00-7.08 (3H, m), 7.65-7.69 (2H, m), 7.97 (1H, d, J = 5.1 Hz), 8.20 (1H, s).

According to the analysis of related databases, 876919-08-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; QUANTICEL PHARMACEUTICALS, INC.; CHEN, Young, K.; KANOUNI, Toufike; NIE, Zhe; STAFFORD, Jeffrey, Alan; VEAL, James, Marvin; WALLACE, Michael, Brennan; WO2014/100818; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 156772-60-0, Adding some certain compound to certain chemical reactions, such as: 156772-60-0, name is 2,5-Dibromo-3-fluoropyridine,molecular formula is C5H2Br2FN, 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 156772-60-0.

7.1b. 5-bromo-2-[(tert-butyldimethylsilanyl)ethynyl]-3-fluoropyridine Under an argon atmosphere, 2.62 mL (13.811 mmol) of tert-butylethynyldimethylsilane was added to a solution of 3.20 g (12.56 mmol) of 2,5-dibromo-3-fluoropyridine, 5.22 mL of triethylamine (37.67 mmol), 59.8 mg (0.31 mmol) of CuI, and 220.3 mg (0.31 mmol) of bis(triphenylphosphane)palladium (II) chloride in 30 mL of absolute THF at 15 C. and the mixture was stirred for 2 hours at RT. 1 mL of tert-butylethynyldimethylsilane was added and the mixture was again stirred for 1 hour at RT. The reaction mixture was evaporated down in vacuo and the residue was taken up in EtOAc. The organic phase was washed with semisaturated aqueous sodium bicarbonate solution, 5% aqueous ammonia, and water, dried over magnesium sulfate, and evaporated down in vacuo. The crude product was purified by column chromatography (silica gel, PE/DCM 9:1). Yield: 1.62 g (41% of theoretical); C13H17BrFNSi (M=314.269); calc.: molpeak (M+H)+: 314/316 (Br); found: molpeak (M+H)+: 314/316 (Br); HPLC-MS: 7.85 minutes (method B).

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. 156772-60-0, 2,5-Dibromo-3-fluoropyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Boehringer Ingelheim International GmbH; US2005/234101; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 106850-34-4 , The common heterocyclic compound, 106850-34-4, name is Imidazo[1,2-a]pyridine-6-carbonitrile, molecular formula is C8H5N3, 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.

An oven dried resealable Schlenk tube was charged with imidazo[1 ,2-a]pyridine-6- carbonitrile (Preparation 1 , 0.30 g, 2.1 mmol), N-benzyl-2-chloro-N-methylpyrimidin-4- amine (Preparation 31 , 0.24 g, 1.0 mmol), potassium acetate (0.21 g, 2.1 mmol) and Lambda/,Lambda/’-dimethylacetamide (3 mL). The Schlenk tube was subjected to three cycles of evacuation-backfilling with argon then tetrakis(triphenylphosphine)palladium (0) (0.12 g, 0.10 mmol) was added. After three further cycles of evacuation-backfilling with argon, the Schlenk tube was capped and placed in an oil bath at 150 C and the mixture was stirred overnight. The mixture was evaporated in vacuum and the residue was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried (MgS04) and evaporated and the residue was purified by flash chromatography (99:1 to 98:2 dichloromethane/methanol) to give the title compound (0.105 g, 30%) as a pale brown solid.LRMS (m/z): 341 (M+1)+.1H-NMR delta (CDCI3): 3.22 (bs, 3H), 4.91 (bs, 2H), 6.40 (d, 1 H), 7.27 – 7.41 (m, 6H), 7.76 (dd, 1 H), 8.31 (d, 1 H), 8.59 (s, 1 H), 10.49 (bs, 1 H)

The synthetic route of 106850-34-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ALMIRALL, S.A.; EASTWOOD, Paul Robert; GONZALEZ RODRIGUEZ, Jacob; BACH TANA, Jordi; PAGES SANTACANA, Lluis Miquel; TALTAVULL MOLL, Joan; CATURLA JAVALOYES, Juan Francisco; MATASSA, Victor Giulio; WO2011/76419; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 116355-16-9, 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. 116355-16-9, name is Imidazo[1,2-a]pyridine-6-carbaldehyde. A new synthetic method of this compound is introduced below.

General procedure: To a 2mL Eppendorf tube was added 10muL of the aldehyde stock solution in DMSO (0.1M, final concentration 10mM), 90muL of buffer (100mM phosphate buffer, 0.1mM PLP, 2M glycine, pH=7.0) and 2muL of a 10.16mg/mL enzyme solution in phosphate buffer (100mM, 1mM PLP, pH=7.0, 0.2mg/mL final protein concentration). The mixture was incubated at 40C and 1100rpm on an Eppendorf Thermomixer. After 1.5h, the reaction was quenched with 200muL ACN/MeOH (1:1), stirred for 5min at 1100rpm and centrifuged at 21,130 xg for 3min. The clear supernatant was analyzed using an UPLC monitoring method (see supplementary information).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,116355-16-9, Imidazo[1,2-a]pyridine-6-carbaldehyde, and friends who are interested can also refer to it.

Reference:
Article; Ligibel, Mathieu; Moore, Charles; Bruccoleri, Robert; Snajdrova, Radka; Biochimica et Biophysica Acta – Proteins and Proteomics; vol. 1868; 2; (2020);,
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. 638218-78-7, name is 2-(6-Bromopyridin-2-yl)propan-2-ol. A new synthetic method of this compound is introduced below., Product Details of 638218-78-7

Into a lOOO-mL 3-necked round-bottom flask, was placed 6-(methylsulfanyl)-2-(prop-2-en-l-yl)-lH,2H,3H- pyrazolo[3,4-d]pyrimidin-3-one (20 g, 89.98 mmol, 1.00 equiv), 2-(6-bromopyridin-2- yl)propan-2-ol (24 g, 111.07 mmol, 1.23 equiv), 1,4-dioxane (500 mL), iodocopper (17.1 g, 89.79 mmol, 1.0 equiv), K2C03 (17.1 g, 122.83 mmol, 1.37 equiv). This was followed by the addition of methyl [2-(methylamino) ethyl] amine (10.8 mL) dropwise with stirring. The resulting solution was stirred overnight at 95C in an oil bath. The resulting mixture was cooled to room temperature. The mixture was then quenched by the addition of 100 mL of water. The resulting mixture was concentrated under vacuum. The residue was extracted with 3×500 mL of ethyl acetate and the organic layers combined. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:5- 1:3). This resulted in 15 g (47%) of l-[6-(2-hydroxypropan-2-yl) pyridin-2-yl]-6-(methylsulfanyl)-2-(prop-2-en-l-yl)-lH,2H,3H- pyrazolo[3,4-d]pyrimidin-3-one as a white solid. LC-MS(ES, m/z) M+l=358

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, 638218-78-7, 2-(6-Bromopyridin-2-yl)propan-2-ol.

Reference:
Patent; NEWAVE PHARMACEUTICAL INC.; CHEN, Yi; (0 pag.)WO2019/165204; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem