Category: pyridine-derivatives

Electric Literature of 17288-32-3, 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 17288-32-3 as follows.

A solution of ethyl 1H-pyrrolo[3,2-b]pyridine-2-carboxylate (23 g, 0.12 mol), 2- bromoethanol (37.9 g, 0.303 mol) and triphenylphosphine (79.4 g, 0.303 mol) intetrahydrofuran was cooled to 0 °C . Diisopropyl azodicarboxylate (61.2 g, 0.303 mol) was added drop-wise over 20 minutes and the resulting mixture was warmed to 25 °C and stirred for 18 hours. After the solvent had been removed under reduced pressure, the residue was diluted with ethyl acetate (300 mL) and extracted with aqueous hydrochloric acid (1 M, 3 x 100 mL). The combined aqueous extracts were basified topH 8 – 9 using saturated aqueous sodium carbonate solution, and the resulting mixture was extracted with ethyl acetate (3 x 100 mL). The combined organic layers were concentrated in vacuo; silica gel chromatography (Eluent: 5:1 petroleum ether I ethyl acetate) provided the product as a white solid. Yield: 25 g, 84 mmol, 70percent. H NMR (400 MHz, CDCI3) oe 8.59 (dd, J=4.5, 1.3 Hz, 1 H), 7.81 (br d, J=8.5 Hz, 1 H), 7.50 (br s, 1 H),7.28 (dd, J=8.5, 4.5 Hz, 1H), 4.92 (t, J=6.7 Hz, 2H), 4.42 (q, J=7.2 Hz, 2H), 3.73 (t, J=6.7 Hz, 2H), 1.44 (t, J=7.2 Hz, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,17288-32-3, its application will become more common.

Reference:
Patent; PFIZER INC.; CHAPPIE, Thomas Allen; CHANDRASEKARAN, Ramalakshmi Yegna; HELAL, Christopher John; LACHAPELLE, Erik Alphie; PATEL, Nandini Chaturbhai; SCIABOLA, Simone; VERHOEST, Patrick Robert; WAGER, Travis T.; (202 pag.)WO2016/203347; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1211534-25-6, 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.1211534-25-6, name is 4-Bromo-5-chloro-2-methoxypyridine, molecular formula is C6H5BrClNO, molecular weight is 222.47, as common compound, the synthetic route is as follows.

[00266j 28F. 4-(4-(Qert-Butyldimethylsilyl)oxy)-3 -fluoropiperidin- 1 -yl)-5 -chloro-2- methoxypyridine: A mixture of 28E (194 mg, 0.830 mmol), 27B (185 mg, 0.830 mmol) and SPhos precatalyst (6.0 mg, 8.3 jimol) in THF (1.7 mL) was purged with argon and a 1 M solution of LHMDS in THF (1.0 mL, 1.0 mmol) was added. The reaction mixturewas heated to 70 C for 2 h and then cooled to rt. Sat. aq. NaHCO3 (10 mL) was added slowly to the reaction mixture. The mixture was then extracted with EtOAc (2 x 10 mL) and the combined organic extracts were washed with water (20 mL) and brine (20 mL), dried (Na2504), filtered, and concentrated. Purification by silica chromatography gave 28F (182 mg, 0.490 mmol, 58% yield). LC-MS Anal. Calc?d for C17H28C1FN2O2Si:374.16,found[M+H] 374.9.

The chemical industry reduces the impact on the environment during synthesis 1211534-25-6, I believe this compound will play a more active role in future production and life.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; ELLSWORTH, Bruce, A.; JURICA, Elizabeth, A.; SHI, Jun; EWING, William, R.; YE, Xiang-Yang; WU, Ximao; ZHU, Yeheng; SUN, Chongqing; WO2014/78609; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 95652-77-0, 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.95652-77-0, name is Methyl 2-chloro-6-methoxynicotinate, molecular formula is C8H8ClNO3, molecular weight is 201.61, as common compound, the synthetic route is as follows.

To a reaction vial containing 7-amino-4-chloro-isoindolin-l-one (365 mg, 2.0 mmol) in dioxane (2.0 mL) was added methyl 2-chloro-6-methoxynicotinate (603 mg, 3.0 mmol), cesium carbonate (1.3 g, 4.0 mmol), copper iodide (152 mg, 80 mmol) and (S,2S)- Nl,N2-dimethylcyclohexane-l,2-diamine (227 mg, 1.6 mmol). The mixture was purged with nitrogen, then warmed to 110 C. The reaction was stirred at 110 C and monitored by LC- MS. Following completion, the reaction was allowed to cool and was then filtered through Celite and rinsed with ethyl acetate. The crude was purified by silica gel chromatography (0- 50% ethyl acetate/hexane) to give the product.

Statistics shows that 95652-77-0 is playing an increasingly important role. we look forward to future research findings about Methyl 2-chloro-6-methoxynicotinate.

Reference:
Patent; CHEMOCENTRYX, INC.; CHEN, Xi; DRAGOLI, Dean, R.; FAN, Junfa; KALISIAK, Jaroslaw; KRASINSKI, Antoni; LELETI, Manmohan, Reddy; MALI, Venkat; MCMAHON, Jeffrey; SINGH, Rajinder; TANAKA, Hiroko; YANG, Ju; YU, Chao; ZHANG, Penglie; (198 pag.)WO2017/87607; (2017); A1;,
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. 6311-35-9, name is 6-Bromonicotinic acid. This compound has unique chemical properties. The synthetic route is as follows. name: 6-Bromonicotinic acid

EXAMPLE 31 2-bromo-5-[(2-methylpyrrolidin-1-yl)carbonyl]pyridine The desired product was prepared by substituting 6-bromonicotinic acid for 2-methylnicotinic acid in Example 1. After workup the crude compound was purified by HPLC on C-18 column using a solvent system increasing over 50 minutes in a gradient of 5% to 100% acetonitrile/water containing 0.01% TFA to provide the desired product as the trifluoroacetate salt. MS m/e 268.9 (M+H)+; 1H NMR (DMSO-d6) delta0.86 (d, 0.75H), 1.25 (d, 2.25H), 1.48-1.63 (m, 1H), 1.66-1.80 (m, 1H), 1.81-1.97 (m, 1H), 2.00-2.13 (m, 1H), 3.27-3.37 (m, 0.5H), 3.45-3.54 (m, 1.5H), 3.88-4.00 (m, 0.25H), 4.09-4.21 (m, 0.75H), 7.72 (d, 1H), 7.87 (dd, 1H), 8.52 (d, 1H).

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, 6311-35-9, 6-Bromonicotinic acid.

Reference:
Patent; Haviv, Fortuna; Brandley, Michael F.; Henkin, Jack; US2003/195192; (2003); A1;,
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. 18438-38-5, name is 2-(Methylthio)pyridine. This compound has unique chemical properties. The synthetic route is as follows. category: pyridine-derivatives

EXAMPLE 7 An aqueous solution consisting of (i) 522.7 g (1.2 mol) of a 27% sodium hypobromite aqueous solution prepared by instilling bromine into a 30% sodium hydroxide aqueous solution and (ii) 8.4 g (0.2 mol) of 95% sodium hydroxide was cooled to 0 C. The 23.8 g of 2-(methylthio)pyridine obtained in Example 6 was instilled into this aqueous solution over 3 hours while keeping the temperature at 0 to 5 C., and stirring was then carried out for 7 hours at 0 to 5 C. The reaction product, which precipitated out as crystals, was filtered, washed with water, and dried, thus obtaining 71.1 g of 2-(tribromomethylsulfonyl)pyridine (purity 99%). The yield relative to the 2-(methylthio)pyridine was 95.0%. The melting point of the 2-(tribromomethylsulfonyl)pyridine obtained was 160 to 161 C.

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, 18438-38-5, 2-(Methylthio)pyridine.

Reference:
Patent; Sumitomo Seika Chemicals Co., Ltd.; US6420564; (2002); B1;,
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

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

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

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

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