Day: April 12, 2022

Electric Literature of 98139-15-2, Adding some certain compound to certain chemical reactions, such as: 98139-15-2, name is 4-Aminopicolinonitrile,molecular formula is C6H5N3, 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 98139-15-2.

Into a 30-mL sealed tube, was placed 2-bromo-5-methoxy-4-[3-(pyrrolidin-l- yl)propoxy]pyridine (314 mg, 1.00 mmol, 1.00 equiv.), 4-aminopyridine-2-carbonitrile (240 mg, 2.01 mmol, 2.00 equiv.), Pd2(dba)3-chloroform (0.1 g, 0.10 equiv.), t-BuXPhos (0.085 g, 0.20 equiv.), Cs2C03 (970 mg, 2.97 mmol, 3.00 equiv.), dioxane (10 mL). The resulting solution was stirred for 16 h at 110 C in an oil bath. The reaction was then quenched by the addition of 50 mL of water. The resulting solution was extracted with 3×30 mL of ethyl acetate and the organic layers combined. The organic layer was washed with 1×50 mL of brine, dried over anhydrous sodium sulfate. The solids were filtered out. The resulting mixture was concentrated under vacuum. The crude product (3 mL) was purified by Flash- Prep-HPLC with the following conditions (CombiFlash-1): Column, C18 silica gel; mobile phase, MeCN_Water=l :5 increasing to MeCN_Water=10: l within 120 min; Detector, UV 254 nm. 70 mg product was obtained. This resulted in 70 mg (20%) of 4-([5-methoxy-4-[3- (pyrrolidin-l-yl)propoxy]pyridin-2-yl]amino)pyridine-2-carbonitrile as an off-white solid.

According to the analysis of related databases, 98139-15-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; EPIZYME, INC.; CAMPBELL, John Emmerson; DUNCAN, Kenneth William; FOLEY, Megan Alene; HARVEY, Darren Martin; KUNTZ, Kevin Wayne; MILLS, James Edward John; MUNCHHOF, Michael John; (586 pag.)WO2017/181177; (2017); 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. 1042141-37-6, name is Methyl 2-bromoimidazo[1,2-a]pyridine-6-carboxylate. A new synthetic method of this compound is introduced below., COA of Formula: C9H7BrN2O2

A mixture of methyl delta-bromo-lJ-diazabicyclo^^.OJnona^^^jdelta-tetraene-S-carboxylate (0.39 mmol, 100 mg), (6-dimethylaminopyridin-3-yl)boronic acid (0.59 mmol, 98 mg), cesium carbonate (1.57 mmol, 510 mg) and Pd(dppf)Cl2*DCM ( 39 mumol, 32 mg) was dissolved in DMF (3 ml). The mixture was stirred at 80 0C for 1 h and filtered. The filtrate lambdavas subjected to preparative HPLC to give 20 mg of the title compound as a white solid. IH NMR (400 MHz, DMSO-^6) delta ppm 9.24 (s, 1 H) 8.69 (d, J=2.02 Hz, 1 H) 8.38 (s, 1 H) 8.02 (dd, J=8.84, 2.27 Hz, 1 H) 7.61 (s, 2 H) 6.73 (d, J=8.84 Hz, 1 H) 3.89 (s, 3 H) 3.08 (s, 6 H); MS m/z (M+H) 297

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, 1042141-37-6, Methyl 2-bromoimidazo[1,2-a]pyridine-6-carboxylate.

Reference:
Patent; ASTRAZENECA AB; WO2008/91195; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 195044-14-5 ,Some common heterocyclic compound, 195044-14-5, molecular formula is C9H12BrN, 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-5: Synthesis of 1-(6-tert-butylpyridin-2-yl)-2-(1-hydroxypropan-2-yl)-6-(methylthio)-1H-pyrazolo[3,4-d]pyrimidin-3(2H)-one To a stirred solution of 2-(1-hydroxypropan-2-yl)-6-(methylthio)-1H-pyrazolo[3,4-d]pyrimidin-3(2H)-one (200 mg, 0.833 mmol, 1.0 eq) and 2-bromo-6-tert-butylpyridine (214 mg, 0.999 mmol, 1.2 eq) in 1,4 dioxane (3 mL) was added potassium carbonate (230 mg, 1.666 mmol, 2.0 eq) and the resulting mixture was purged with nitrogen for 30 min followed by addition of copper iodide (31 mg, 0.666 mmol, 0.2 eq), and N,N’-dimethylethylenediamine (DMEDA) (30 mg, 0.333 mmol, 0.4 eq) and again purged with nitrogen for 10 min. The resultant mixture was heated at 100 C. for 5 h. The reaction was monitored by TLC. After completion of reaction, the reaction mixture was diluted with water and extracted with EtOAc (150 mL*2). Combined organic layer was washed with water (50 mL) brine solution (50 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure to afford crude which was purified by flash chromatography (Teledyne Isco Rf+); compound eluting 95% EtOAc/Hexane to afford 1-(6-tert-butylpyridin-2-yl)-2-(1-hydroxypropan-2-yl)-6-(methylthio)-1H-pyrazolo[3,4-d]pyrimidin-3(2H)-one (100 mg, 32.25%) as off white solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,195044-14-5, its application will become more common.

Reference:
Patent; giraFpharma LLC; Chakravarty, Sarvajit; PHAM, Son Minh; Kankanala, Jayakanth; AGARWAL, Anil Kumar; PUJALA, Brahmam; SONI, Sanjeev; ARYA, Satish K.; PALVE, Deepak; Gupta, Ashu; KUMAR, Varun; (498 pag.)US2019/106427; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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.83766-88-5, name is 2-(tert-Butoxy)pyridine, molecular formula is C9H13NO, molecular weight is 151.21, as common compound, the synthetic route is as follows.Product Details of 83766-88-5

Carboxylic acid (0.2 g, 1.64 mmol), tert-butoxypyridine (0.33 g, 2.21 mmol) and boron trifluoride diethyl etherate (0.31 g, 2.21 mmol) in dry PhCH3 (2 mL) were added to a 20-ml vial. The reaction mixture was then allowed to stir at room temperature for 30 min before quenching with anhydrous NaHCO3. The reaction mixture was diluted with ethyl acetate (30 mL), then washed with water (20 mL), followed by brine (20 mL). The organic layer was dried over anhydrous sodium sulfate and carefully concentrated under reduced pressure. The resulting residue was then purified by flash column chromatography on silica gel with 0:4 to 1:4 dichloromethane/hexane as eluent to yield the desired product 5a as a colorless oil.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,83766-88-5, 2-(tert-Butoxy)pyridine, and friends who are interested can also refer to it.

Reference:
Article; La, Minh Thanh; Kim, Hee-Kwon; Tetrahedron; vol. 74; 27; (2018); p. 3748 – 3754;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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.90145-48-5, name is 5-Bromopyridine-2-carboxamide, molecular formula is C6H5BrN2O, molecular weight is 201.02, as common compound, the synthetic route is as follows.Recommanded Product: 5-Bromopyridine-2-carboxamide

Example 10 Preparation of 5-bromo-N-(2,2,2-trichloro-1-(4- ethylcvcloheylamino)ethyl)picolinamide (Compound-46) and 5-bromo-N-(2,2,2-trichloro-1-(4- ethylcvclohexylamino)ethyl)picolinamide (Compound-47)[00144] 5-Bronnopicolinannide 112 (1.29 g, 6.4 mmol) and chloral (1.25 ml_) in dioxane (10 ml_) were heated to 100 0C. The mixture was concentrated to give 5- bromo-N-(2,2,2-trichloro-1 -hydroxyethyl)picolinamide 122 (99%). [00145] A solution of 5-bromo-N-(2,2,2-thchloro-1 -hydroxyethyl)picolinamide 122 (0.83 g, 2.39 mmol) in chloroform (20 ml_) was reacted with PCI5 (0.51 g, 2.33 mmol) at 50 0C for 30 minutes. The mixture was cooled to -78 0C and 4-ethylcyclohexanamine was added (1 g, 7.5 mmol). After 1 hour, the mixture was warmed to room temperature. The reaction mixture was subjected to an aqueous work-up and the product extracted with chloroform. The organic solution was concentrated onto silica gel and the product was eluted (flash: 97:3 hexane:ether then prep-HPLC: Phenomenex Luna column (Sitheta2), 10 micron, 250×50 mm, 150 mL/minute; 3:7 hexanes:dichloromethane) to give first eluting fraction: 5-bromo-N-(2,2,2-trichloro-1 -(4- ethylcyclohexylamino)ethyl)picolinamide (Compound-46, 106 mg) 1H NMR (300 MHz, CDCI3): delta = 8.64 (dd, J = 2.1 , 0.6 Hz, 1 H), 8.26 (d, J = 9.9 Hz, 1 H), 8.11 (dd, J = 8.4, 0.6 Hz, 1 H), 8.01 (dd, J = 8.4, 2.4 Hz, 1 H), 5.56 (t, J = 9.3 Hz, 1 H), 2.96 (brs, 1 H), 1.80- 1.71 (m, 2H), 1.59-1.21 (m, 10H), 0.85 (t, J = 7.2 Hz, 3H), and second eluting fraction: 5-bromo-N-(2,2,2-trichloro-1 -(4-ethylcyclohexylamino)ethyl)picolinamide (Compound- 47, 166 mg) 1H NMR (300 MHz, CDCI3): delta = 8.64 (dd, J = 2.1 , 0.6 Hz, 1 H), 8.30 (d, J = 9.9 Hz, 1 H), 8.11 (dd, J = 8.4, 0.9 Hz, 1 H),8.01 (dd, J = 8.4, 2.1 Hz, 1 H), 5.50 (t, J = 8.7 Hz, 1 H), 2.68-2.58 (m, 1 H), 2.16-2.07 (m, 1 H), 1.86-1.70 (m, 4H), 1.27-1.01 (m, 6H), 0.96-.087 (m, 1 H) 0.83 (t, J = 7.5 Hz, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,90145-48-5, 5-Bromopyridine-2-carboxamide, and friends who are interested can also refer to it.

Reference:
Patent; ALLERGAN, INC.; NGUYEN, Phong X.; HEIDELBAUGH, Todd M.; CHOW, Ken; GARST, Michael E.; WO2011/19681; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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.866775-18-0, name is Methyl 3-amino-6-bromo-5-(trifluoromethyl)picolinate, molecular formula is C8H6BrF3N2O2, molecular weight is 299.05, as common compound, the synthetic route is as follows.Recommanded Product: Methyl 3-amino-6-bromo-5-(trifluoromethyl)picolinate

3-Amino-6-bromo-5-trifluoromethyl-pyridine-2-carboxylic acid methyl ester (Intermediate A step 4) (2 g, 6.69 mmol) was suspended in toluene (8 ml), then p-toluenesulfonic acid (TsOH) (0.1 15 g, 0.669 mmol) and acetonylacetone (0.941 ml, 8.03 mmol) was added. The reaction mixture was heated at reflux for 2 h and allowed to cool to RT overnight. The resulting dark red/ black solution was concentrated under reduced pressure to remove toluene and the crude residue was diluted with EtOAc (200 ml), washed with NaHC03 (50 ml), dried (MgS04) and concentrated under reduced pressure to give a brown solid; LC-MS Rt = 5.58 min [M+H]+ 377/379 (Method 10minl_C_v002). 1 H NMR (400 MHz, DMSO-d6) ? 8.50 (1 H, s), 7.77 (2H, s), 5.83 (3H, s), 1.90 (6H, s); 19F NMR (400 MHz, DMSO-d6) ? -62.26 (CF3, s)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,866775-18-0, Methyl 3-amino-6-bromo-5-(trifluoromethyl)picolinate, and friends who are interested can also refer to it.

Reference:
Patent; NOVARTIS AG; LEGRAND, Darren Mark; WO2013/38378; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 6318-51-0, Adding some certain compound to certain chemical reactions, such as: 6318-51-0, name is (4-Chlorophenyl)(pyridin-2-yl)methanone,molecular formula is C12H8ClNO, 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 6318-51-0.

Under argon atmosphere, cinchonine (440 mg, 1.0 mmol) was suspended in tetrahydrofuran (absolute, 2.0 mL), and to this suspension was added a Reformatsky reagent (0.5 M; 8.0 mL, 4.0 mmol) dropwise under ice-cooling. After stirring for 10 minutes, pyridine (0.30 mL, 2 mmol) was added thereto dropwise. After stirring for 20 minutes under ice-cooling, the mixture was cooled to -40C. A solution of 2- (4-chlorobenzoyl) pyridine (218 mg, 1. 0 mmol) in tetrahydrofuran (absolute, 4.0 mL) was added dropwise over 10 minutes, and the mixture was stirred at -40 C for 4 hours. To this reaction solution was added 1N HCl (20 mL) , which was then extracted with ethyl acetate (20 mL×2). The extracted solution was washed successively with an aqueous saturated sodium bicarbonate solution and an aqueous saturated sodium chloride solution. After the organic layer was dried with sodium sulfate, the solvent was removed under reduced pressure. The residue was analyzed with high performance liquid chromatography. Consequently, the yield was 81% and the enantiomer excess was 91%.1H NMR (400 MHz, CDCl3) delta: 1.33 (9H, s), 3.08 (1H, d, J = 16.0 Hz), 3.49 (1H, d, J = 16.0 Hz), 5.52 (1H, s), 7.1-7.7 (7H, m), 8.4-8.6 (1H, m). IR (KBr) nucm-1: 3358, 2977, 1694, 1591, 1490, 1467, 1368, 1159, 1090, 1013, 830, 785, 755, 591. High Performance Liquid Chromatography Column: CHIRALCEL OJ Mobile phase: Hexane/Ethanol/Trifluoroacetic acid (99/1/0.1) Flow rate: 0.5 mL/min. Detection: UV (254 nm) Temperature: Room Temperature Retention Time: 24.5 minutes (enantiomer 17.3 minutes)

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. 6318-51-0, (4-Chlorophenyl)(pyridin-2-yl)methanone, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Takeda Chemical Industries, Ltd.; EP1489070; (2004); 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. 161117-83-5, name is tert-Butyl (2-methoxypyridin-3-yl)carbamate. A new synthetic method of this compound is introduced below., COA of Formula: C11H16N2O3

A) tert-butyl (4-benzyl-2-methoxypyridin-3-yl)carbamate [0412] To a solution of tert-butyl (2-methoxypyridin-3-yl)carbamate (25.1 g) and N,N,N’,N’-tetramethylethane-1,2-diamine (40.6 mL) in diethyl ether (374 mL) was added 1.6M n-butyllithium hexane solution (168 mL) at -78C, and the mixture was stirred under argon atmosphere at 0C for 1 hr. To the reaction mixture was added benzyl bromide (24.9 g) at -78C, and the mixture was stirred under argon atmosphere at room temperature for 4 hr. To the reaction mixture was added saturated aqueous sodium hydrogencarbonate solution at room temperature, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (basic silica gel, ethyl acetate/hexane), and crystallized from ethyl acetate and hexane to give the title compound (25.4 g). 1H NMR (300 MHz, CDCl3) delta 1.50 (9H, s), 3.96 (3H, s), 4.00 (2H, s), 5.99 (1H, brs), 6.60 (1H, d, J = 5.3 Hz), 7.12-7.33 (5H, m), 7.88 (1H, d, J = 5.3 Hz).

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, 161117-83-5, tert-Butyl (2-methoxypyridin-3-yl)carbamate.

Reference:
Patent; Takeda Pharmaceutical Company Limited; NARA, Hiroshi; DAINI, Masaki; KAIEDA, Akira; KAMEI, Taku; IMAEDA, Toshihiro; KIKUCHI, Fumiaki; EP2857400; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 490-11-9, 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. 490-11-9, name is Pyridine-3,4-dicarboxylicacid, molecular formula is C7H5NO4, 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.

10265] WXO18-1 (40.00 g, 239.35 mmol, 1.00 eq) was dissolved in anhydrous methanol (1.00 L), then concentrated sulfuric acid (11.98 g, 119.67 mmol, 6.51 mE, 98% purity, 0.50 eq) was added at 85 C. The mixture was stirred under nitrogen condition for 40 h. After reaction, the reaction liquid was concentrated under vacuum, then the concentrated solution was slowly added to saturated sodium bicarbonate solution (1,500 mE). The resulting mixture was stirred until there was no bubble generated, and extracted with ethyl acetate (1,000 mLx3). The organic phase was washed with saturated sodium chloride solution (800 mLx3), dried with anhydrous sodium sulfate and filtered. The filtrate was dried by rotary evaporation to obtain the brown oily compound WXO18-2. ?H NMR (400 MHz, CDC13) oe ppm: 9.06 (s, 1H), 8.82 (d, J4.90 Hz, 1H), 7.49 (d, J5.02 Hz, 1H), 3.94 (m, 6H).

According to the analysis of related databases, 490-11-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SHENZHEN SALUBRIS PHARM CO LTD.; Wu, Chengde; Yan, Jie; Xu, Wenjie; Yu, Tao; Li, Ning; Chen, Shuhui; US2018/305346; (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. 112193-41-6, name is 5-Bromonicotinohydrazide. A new synthetic method of this compound is introduced below., Computed Properties of C6H6BrN3O

Example 251-{[5-(5-Bromo-3-pyridinyl)-1,3,4-oxadiazol-2-yl]methyl}-4-chloro-2- (difluoromethyl)-1H-indole-5-carbonitrile A. 5-Bromo-A/’-(chloroacetyl)-3-pyridinecarbohydrazide; To an ice-cold suspension of 5-bromo-3-pyhdinecarbohydrazide (3.0 g, 13.88 mmol) in anhydrous CH2CI2 (60 ml_) was added 4-methyl-morpholine (2.1 g, 20.82 mmol), followed by dropwise addition of chloroacetyl chloride (1.88 g,16.67 mmol). The cold bath was then removed and the mixture stirred at rt for 15 h. Heavy precipitation occurred and the mixture was diluted with additional CH2CI2 (50 ml_) and stirring continued for 24 h. The solids were collected by filtration and washed with CH2CI2 to afford the title compound (3.66 g, 90% yield): MS (ES) m/z 292 and 294 (M+1 Br isotopes).

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, 112193-41-6, 5-Bromonicotinohydrazide.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2008/42571; (2008); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem