Day: September 8, 2021

Electric Literature of 13959-02-9 ,Some common heterocyclic compound, 13959-02-9, molecular formula is C6H4BrNO2, 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.

General procedure: (a) Halopicolinic acid (2.69 g, 13.31 mmol), phenylboronic acid(2.44 g, 19.97 mmol), 2M aqueous potassium carbonate (20 mL), palladiumacetate (0.14 g, 0.62 mmol), triphenylphosphine (0.70 g,2.67 mmol), and 1,4-dioxane (50 mL) were mixed and refluxed undernitrogen for 24 h. The reaction mixture was cooled to room temperatureand added aqueous sodium hydroxide (NaOH) (1 M, 35 mL) and dichloromethane(CH2Cl2) (20 mL). The aqueous layer was acidified topH=2-3 by using citric acid (1 M) followed by extraction with Etheracetate (EtOAc). The combined organic layers were dried over magnesiumsulfate (MgSO4), filtered, and concentrated to give off the crudeproduct. A mixture of the crude product and 50 g polyphosphoric acidwas heated at 210 C for 5 h and then stop the reaction. After themixture had cooled to 140 C, some ice and water were added slowly todilute the mixture. Then aqueous sodium hydroxide was added to makethe pH?7, and the aqueous layer was extracted with EtOAc. Thecombined extracts were dried with MgSO4 and concentrated to provide0.96 g. The residue was purified by flash chromatography on silica gel(eluent: petroleum ether/ethyl acetate 6:1) to give the desired product.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,13959-02-9, its application will become more common.

Reference:
Article; Wu, Peng; Zhu, Jun; Zhang, Zhen; Dou, Dehai; Wang, Hedan; Wei, Bin; Wang, Zixing; Dyes and Pigments; vol. 156; (2018); p. 185 – 191;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 88912-27-0, 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.88912-27-0, name is 3-Chloroisonicotinic acid, molecular formula is C6H4ClNO2, molecular weight is 157.55, as common compound, the synthetic route is as follows.

Reference Production Example 33A mixture of 0.60 g of 2-amino-4-chloro-5-trifluoromethylphenol, 0.43 g of 3- chloroisonicotinic acid, 0.67 g of WSC and 5 ml of pyridine was stirred while heating at 80C for three hours. The reaction mixture was cooled to room temperature, and then water was added, followed by extraction with ethyl acetate three times. The combined organic layers were washed with water and a saturated sodium chloride solution, dried anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 0.67 g of 3-chloro-N-[5-chloro-2- hydroxy-4-trifluoromethylphenyl]isonicotinamide. 1H-NMR (DMSO-di) delta: 8.75 (s, IH), 8.64 (d, J=4.8 Hz, IH), 8.36 (s, IH), 7.62 (d, J=4.8 Hz, IH), 7.28 (s, IH)

Statistics shows that 88912-27-0 is playing an increasingly important role. we look forward to future research findings about 3-Chloroisonicotinic acid.

Reference:
Patent; SUMITOMO CHEMICAL COMPANY, LIMITED; OTSUKI, Junko; WO2011/49222; (2011); 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. 1034467-80-5, name is 5-Cyclopropyl-2-fluoropyridine. A new synthetic method of this compound is introduced below., category: pyridine-derivatives

A mixture of 5-cyclopropyl-2-fluoropyridine (543 mg, 2.92 mmol), (R)-tert-butyl 3- aminopyrrolidine-l-carboxylate (400 mg, 2.92 mmol) and Cs2C03 (1904 mg, 5.84 mmol) in DMSO (2 mL) was stirred at 160 C for 24 hours. The mixture was cooled to RT diluted with water (20 mL) and extracted with EtOAc (20 mL*3). The combined organic phase was concentrated and the residue was purified by flash chromatography on silica gel (PE/EtOAc = 2/1) to afford (R)-tert- butyl 3-((5-cyclopropylpyridin-2-yl)amino)pyrrolidine-l-carboxylate (35 mg, 4%) as a yellow solid. [M+H] Calc?d for CI7H25N302, 304.1; Found, 304.1.

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, 1034467-80-5, 5-Cyclopropyl-2-fluoropyridine.

Reference:
Patent; KINNATE BIOPHARMA INC.; KANOUNI, Toufike; ARNOLD, Lee D.; KALDOR, Stephen W.; MURPHY, Eric A.; TYHONAS, John; (0 pag.)WO2020/6497; (2020); 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.13534-98-0, name is 4-Amino-3-bromopyridine, molecular formula is C5H5BrN2, molecular weight is 173.01, as common compound, the synthetic route is as follows.HPLC of Formula: C5H5BrN2

To a stirred solution of 3-bromopyridin-4-amine (1.0 g, 5.780 mmol) in dichloromethane (20 mL) was added di isopropyl ethylamine(1.5mL, 8.678mmo1) followed by acetyl chloride(0.45mL, 6.345mmo1) at 0 C and starred at room temperature for 12 h. After completion of the reaction mixture was diluted with dichloromethane (20 mL) and washed with saturated sodium bicarbonate solution (20 mL), dried over sodium sulphate, and concentrated. The crude product obtained as N-(3-bromopyridin-4-yl)acetamide as off white solid.(1 .24 g, 80%).1H NMR (400 MHz, DMSO-d6) oe 3.62 (s, 3H), 6.43 (brs, 2H), 6.77 (d, J= 8.16Hz, 1H), 7.33 (d,J= 2.05Hz, 1H), 7.65 (dd, J= 8.5Hz, 1H)LC-MS m/z (M+H): 215.0

At the same time, in my other blogs, there are other synthetic methods of this type of compound,13534-98-0, 4-Amino-3-bromopyridine, and friends who are interested can also refer to it.

Reference:
Patent; BIOIMICS AB; KIRSEBOM, Leif; UPADHAYAYA, Ram Shankar; KETHIRI, Raghava Reddy; VIRTANEN, Anders; (308 pag.)WO2017/222466; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1034667-22-5, 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 1034667-22-5, name is 5-Fluoro-1H-pyrazolo[3,4-b]pyridin-3-amine. This compound has unique chemical properties. The synthetic route is as follows.

Reagents and conditions: (i) mCPBA, EtOAc; (ii) POCl3; (iii) PdPPh3) 2C12, Ba(OH)2, DME-H2O, 110 0C; (iv) 5-fluoro-lH- pyrazolo [3, 4-b] pyridin-3-amine, Pd(OAc)2, Xantphos, K2CO3, dioxane, 120 0C.[0054] Scheme III above shows a general synthetic route that is used for preparing the compounds III-5. Compounds of formula III-5 can be prepared from intermediate III-l. The formation of chloropyridine derivative III-2 is achieved by treating the corresponding pyridine III-l with m-CPBA in EtOAc followed by conversion of the corresponding N-oxide to the chloropyridine by treating it with POCl3. Intermediate III-2 is then reacted with the corresponding boronic acid derivative to yield compound III- 3 using Suzuki coupling conditions well known for those skilled in the art. This reaction is amenable to a variety of boronic acid derivatives. The pyridine III-3 is then converted in a chloropyridine derivative III-4 using the same two step procedures as used in step 1, m-CPBA oxidation followed by POCl3 treatment. Intermediate III-4 is then treated with 5-fluoro-lH- pyrazolo [3, 4-b] pyridin-3-amine in the presence of Pd as a catalyst to yield the final compound III-5.

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 1034667-22-5, 5-Fluoro-1H-pyrazolo[3,4-b]pyridin-3-amine.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; WO2009/18415; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 63071-09-0, 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.63071-09-0, name is 2-Hydroxymethyl-3-methylpyridine, molecular formula is C7H9NO, molecular weight is 123.15, as common compound, the synthetic route is as follows.

A portion (605.3 mg) of the obtained product was dissolved in chloroform (30 ml) and then added with manganese dioxide (3.03 g) (chemicals treated, manufactured by Wako Pure Chemical Industries, Ltd.), followed by stirring at 70C for 2 hours. After completion of reaction, the catalyst was removed by filtration with Celite and the solvent was concetrated. The residue was purified by silica gel column chromatography (chloroform/ethyl acetate=1:1), to thereby obtain a light orange liquid of the subject compound (419.8 mg). MS (FAB,Pos.) :m/z= 122 [M+1]+1H-NMR(500MHz,CDCl3) : delta=2.67(3H,s),7.40(1H,dd,J=7.8,4.6Hz),7.64(1H,d,J=7.8Hz) ,8.67(1H,d,J=4.6Hz) ,10.2(1H,s) .

Statistics shows that 63071-09-0 is playing an increasingly important role. we look forward to future research findings about 2-Hydroxymethyl-3-methylpyridine.

Reference:
Patent; Kureha Chemical Industry Co., Ltd.; EP1431290; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 83004-10-8, 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. 83004-10-8, name is 2-Bromo-6-(bromomethyl)pyridine, molecular formula is C6H5Br2N, 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 of 0.050 g (0.169 mmol) of 3-(3,4-dimethyl-benzoyl)-6-fluoro-lH- quinolin-4-one 4tt in 1.0 mL of tetrahydrofuran was added 0.4 mL (0.5 M in toluene, .203 mmol) of potassium hexamethyldisilazide and the reaction solution was stirred for 5 min, followed by the addition of 50.9 mg (0.203 mmol) of 2-bromo-6-bromomethyl-pyridine in 0.5 ml of tetrahydrofuran. The resultant solution was stirred at 60 C for 3 h. The reaction solution was quenched by the addition of water and the aqueous phase was extracted with 3 x 5 mL of ether. The combined organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to yield 58 mg of l-(6-Bromo-pyridin-2-ylmethyl)-3-(3,4- dimethyl-benzoyl)-6-fluoro-lH-quinolin-4-one 4tt as a yellow solid: LC-MSD, m/z for C24Hi8BrFN2O2, [M+H] = 465.4, 466.5, 467.4, 468.4; Reverse phase HPLC gradient, 20-95% acetonitrile with 0.1% TFA in 4 minutes, retention time = 2.8 min;1H NMR (400 MHz, CDCl3): delta 8.27 (IH, s), 8.12 (IH, m), 7.64 (IH, s), 7.56 (IH, m), 7.51 (IH, m), 7.47 (IH, m), 7.40-7.34 (2H, m), 7.19 (IH, m), 7.00 (IH, m), 5.46 (2H, s), 2.32 (3H, s), 2.31 (3H, s).

According to the analysis of related databases, 83004-10-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CHEMOCENTRYX, INC.; WO2007/59108; (2007); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 5346-38-3, Pyridine-2-carbothioamide, 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, 5346-38-3, blongs to pyridine-derivatives compound. Product Details of 5346-38-3

To a solution of 2-Bromo-1-(4-nitro-phenyl)-propan-1-one (6.13 g, 23.75 mmol) in absolute EtOH (200 ml) was added pyridine-2-carbothioic acid amide (3.28 g, 23.75 mmol). The mixture was heated to reflux for 2 h, after which it was concentrated to dryness, and the resulting solid was filtered and washed with Et2O to provide 2-[5-Methyl-4-(4-nitro-phenyl)-thiazol-2-yl]-pyridine (6.08 g, 85%) as a solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,5346-38-3, its application will become more common.

Reference:
Patent; Alam, Muzaffar; Du Bois, Daisy Joe; Hawley, Ronald Charles; Kennedy-Smith, Joshua; Minatti, Ana Elena; Palmer, Wylie Solang; Silva, Tania; Wilhelm, Robert Stephen; US2011/71150; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 16063-69-7, 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 16063-69-7, name is 2,4,6-Trichloropyridine. This compound has unique chemical properties. The synthetic route is as follows.

Based on the coupling described by Tan et al.63 trans-2-Phenylvinylboronic acid (2.546 g, 17.2 mmol), K3P04 (7.307 g, 34.4 mmol), and PdC12(PPh3)2 (0.362 g, 0.52 mmol) were dissolved in 100 mL THF. To this mixture, 2,4,6-trichloropyrimidine (3.156 g, 17.2 mmol) dissolved in 20 mL THF was added producing a cloudy yellow suspension. H20 (15 mL) were added, and the now clear solution was heated at reflux for 7 h. Approximately 100 mL of H20 were added, and the biphasic mixture was extracted three times with ether. The combined organic layers were washed with brine, dried over anhydrous MgSO4, and the solvent removed with a rotary evaporator. The product purified by column chromatography (5-10% EtOAc in hexanes) to provide 1 (3.161 g, 73%). ?H NMR (500 MHz, CDC13) oe 6.95 (d, J=15.87 Hz, 1 H), 7.22 (s, 1 H), 7.41 (m, 3 H), 7.59 (dd, J=7.45, 2.08 Hz, 2 H), 7.96 (d, J=15.87 Hz, 1 H). ?3C NMR (500 MHz, CDC13) oe 117.1, 123.0, 128.2,129.2, 130.6, 134.8, 140.9, 160.7, 162.8, 166.6. HRMS (ESIj m/z calcd for C,2H9N2Cl2251.0143, found 251.0101. mp 119-121 C (recryst. from EtOAc/hex)

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 16063-69-7, 2,4,6-Trichloropyridine.

Reference:
Patent; THE BOARD OF TRUSTEES OF THE UNIVERSITY OF ILLINOIS; DUCKE UNIVERSITY; KATZENELLENBOGEN, John; MCDONNELL, Donald; NORRIS, John, D.; PARENT, Alexander; POLLOCK, Julie; GUNTHER, Jillian; CARLSON, Kathryn, E.; MARTIN, Teresa; WO2015/48246; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 13600-47-0, 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.13600-47-0, name is 5-Aminonicotinonitrile, molecular formula is C6H5N3, molecular weight is 119.12, as common compound, the synthetic route is as follows.

(5)-4-Bromo-2,2-difluoro-7-((trifluoromethyl)sulfonyl)-2,3-dihydro-lH-inden- l-ol (23 mg, 0.060 mmol) was dissolved in 1,4-dioxane (0.20 mL) and treated with 3- pyridinecarbonitrile, 5-amino- (8.6 mg, 0.070 mmol), cesium carbonate (27.5 mg, 0.080 mmol), palladium (II) acetate (0.68 mg, 0.003 mmol), and Xantphos (3.5 mg, 0.010 mmol). After cooling, the mixture was diluted with water and ethyl acetate then separated. This mixture didn’t separate well and there was insoluble yellow solid present, which was removed by filtration. The aqueous was washed with ethyl acetate and the combined organics were washed with saturated NaHC03, saturated NaCl, dried over Na2S04, and concentrated in vacuo to a dark residue. The crude material was chromatographed on Si02 eluting with a gradient of ethyl acetate / hexanes. The product was recovered as light tan solid, (12 mg, 47%). LCMS ESI (+) m/z (M+H) 420; 1H NMR (400 MHz, CDC13 plus CD3OD): delta 8.66 (s, 1H), 8.60 (s, 1H), 7.79-7.75 (m, 2H), 7.22-7.20 (m, 1H), 5.30 (d, 1H), 3.92-3.90 (m, 1H), 3.46-3.32 (m, 1H), 3.31-3.21 (m, 1H).

Statistics shows that 13600-47-0 is playing an increasingly important role. we look forward to future research findings about 5-Aminonicotinonitrile.

Reference:
Patent; PELOTON THERAPEUTICS, INC.; DIXON, Darryl, David; GRINA, Jonas; JOSEY, John, A.; RIZZI, James, P.; SCHLACHTER, Stephen, T.; WALLACE, Eli, M.; WANG, Bin; WEHN, Paul; XU, Rui; YANG, Hanbiao; (237 pag.)WO2016/144825; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem