Day: February 3, 2021

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. 131747-63-2, name is 4-Bromopicolinaldehyde. This compound has unique chemical properties. The synthetic route is as follows. category: pyridine-derivatives

To a solution of 4-bromopicolinaldehyde (10 g, 53.76 mmol) in CHCI3 (200.0 mL) was added diethylaminosulfur trifluoride (8.5 mL, 64.51 mmol) at 0C under argon. The reaction mixture was stirred overnight while the temperature was raised to room temperature. The reaction was quenched by addition of aqueous NaHC03 and further diluted with CH2CI2. The solids were filtered off through a pad of celite. The organic layer was separated and aqueous phase was extracted with CH2CI2 (3x). The organic phase dried over Na2S04. The suspension was concentrated to dryness and the resulting crude product was purified by Teledyne-Isco flash system by using Hexane/EtOAc, 0 to 20% of ethyl acetate in hexane to provide compound 16 as light yellow liquid (3.5 g, 32% yield). lH NMR (400 MHz, DMSO-d6) delta (ppm): 8.79 (d, 1H), 7.98 (s, 1H), 7.80 (d, 1H), 4.86 (s, 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, 131747-63-2, 4-Bromopicolinaldehyde.

Reference:
Patent; NANTBIO, INC.; TAO, Chunlin; POLAT, Tulay; YU, Chengzhi; (65 pag.)WO2019/5297; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1173081-96-3 ,Some common heterocyclic compound, 1173081-96-3, molecular formula is C8H13ClN2O, 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.

To a mixture of 5-bromo-2-methyl-3-(2-methylpiperidin-1-yl)benzoic acid (250mg, 0.801 mmol), 3-(aminomethyl)-4,6-dimethylpyridin-2(1H)-one hydrochloride salt(160 mg, 0.848 mmol) and HOAt (110 mg, 0.808 mmol) in dichloromethane (DCM) (15 mL) was added N-methylmorpholine (100 )lL, 0.910 mmol), followed by EDC free base(150 mg, 0.966 mmol). The reaction was stirred at room temperature for 18 h. LCMSshowed that the reaction was complete. The reaction was concentrated under vacuum thenpurified by silica gel chromatography (Analogix, SF25-40 g, 0 to 4% MeOH in CH2Cb) togive 5-bromo-N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-2-methyl-3-(2-methylpiperidin-1-yl)benzamide (268 mg, 0.600 mmol, 75.0% yield), after trituration with20% CH2Cb in hexanes, filtration, and drying under vacuum as an off-white solid. 1HNMR (400MHz, DMSO-d6) 8 = 11.48 (s, 1 H), 8.23 (t, J= 4.9 Hz, 1 H), 7.26 (d, J= 1.8Hz, 1 H), 7.09 (d, J= 2.0 Hz, 1 H), 5.86 (s, 1 H), 4.24 (d, J= 5.1 Hz, 2 H), 3.08-2.96 (m,1 H), 2.84 ( d, J = 11.4 Hz, 1 H), 2.49 – 2.39 (m, 1 H), 2.18 (s, 3 H), 2.16 (s, 3 H), 2.11 (s, 3H), 1.81 -1.66 (m, 2 H), 1.64-1.52 (m, 2 H), 1.48-1.25 (m, 2 H), 0.77 (d,J= 6.1 Hz, 3H). MS(ES)+ m/e 446.3 [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,1173081-96-3, its application will become more common.

Reference:
Patent; GLAXOSMITHKLINE LLC; BURGESS, Joelle, Lorraine; DUQUENNE, Celine; KNIGHT, Steven, David; MILLER, William, Henry; NEWLANDER, Kenneth, Allen; VERMA, Sharad, Kumar; WO2013/173441; (2013); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 100704-10-7, 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 100704-10-7, name is (2-Chloropyridin-4-yl)methanol. This compound has unique chemical properties. The synthetic route is as follows.

Step 4b: Synthesis of 4-(bromomethyl)-2-chloropyridine (2-chloropyridin-4-yl)methanol (1.1 g, 7.3 mmol) is dissolved in 20 mL DCM; flushed with argon and cooled to 0 C. PBr, (0.76 mL; 8.1 mmol) is added drop wise via a syringe (solution turned cloudy) and reaction mixture is stirred at RT for 3 h. Cooled to 0 C and quenched with 5 mL water. The reaction mixture is ad j usted to pi f 7 by the addition of 2M K2CO3. The aqueous and organic layer are separated and the aqueous layer is extracted 3x with EtOAc. The organic layers are combined, dried over anhydrous sodium sulfate, filtered and deposited on silica. Column chromatography on silica gel (pre-washed with 1% NEt3), using a solvent gradient from hexanes to EtOAc lead to the isolation of the product as pale pink crystals (700 mg, 50% yield based on recovered starting material). NMR (300 MHz, CDCI3) delta 8.37 (d, J = 5.1 Hz, 1H), 7.35 (s, 1H), 7.27 – 7.20 (m, 1 H ), 4.35 (s, 21 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 100704-10-7, (2-Chloropyridin-4-yl)methanol.

Reference:
Patent; THE ROYAL INSTITUTION FOR THE ADVANCEMENT OF LEARNING/MCGILL UNIVERSITY; TSANTRIZOS, Youla, S.; DE SCHUTTER, Joris, Wim; LIN, Yih-Shyan; WO2011/147038; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1215387-58-8, 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.1215387-58-8, name is 5-Bromo-1H-pyrrolo[2,3-c]pyridine, molecular formula is C7H5BrN2, molecular weight is 197.03, as common compound, the synthetic route is as follows.

To a stirred solution of 5-bromo-1H-pyrrolo[2,3-c]pyridine (500 mg, 2.53 mmol) in DCM (40mL), anhydrous AlCb (675 mg, 5.07 mmol) was added at 0C. The reaction mixture was stirred at RT for 15 minutes and then, acetyl chloride (396 mg, 5.07 mmol) was added. The reaction mixture was allowed to stirred at RT for 16h. The progress of the reaction was monitored by LCMS. The reaction mixture was concentrated under reduced pressure and poured into crushed ice and neutralized with 2N NaOH: The solid precipitated was filtered and dried under vacuum to afford the title compound (600mg, 98.90%). LC-MS (method 20): Rt = 1.61 min; m/z = 239.06 (M+H+).

Statistics shows that 1215387-58-8 is playing an increasingly important role. we look forward to future research findings about 5-Bromo-1H-pyrrolo[2,3-c]pyridine.

Reference:
Patent; ORYZON GENOMICS, S.A.; SALAS SOLANA, Jorge; CARCELLER GONZALEZ, Elena; ORTEGA MUNOZ, Alberto; (195 pag.)WO2018/149986; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 67346-74-1, 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 67346-74-1, name is 3-Ethynylpyridin-2-amine. This compound has unique chemical properties. The synthetic route is as follows.

Reference Example 70 3-(3-(4-Butyl-benzyl)-isoxazol-5-yl)-pyridin-2-ylamine; To a tetrahydrofuran (3 mL) solution of (4-butyl-phenyl)-acetohydroximoyl chloride (150 mg, 0.665 mmol) described in Manufacturing Example 70-1-3 and 3-ethynyl-pyridin-2-ylamine (50 mg, 0.424 mmol) described in Manufacturing Example 1-2-3 was added triethylamine (232 muL, 1.66 mmol) at room temperature, which was stirred for 8 hours at 50¡ã C. Water was added to the reaction solution at room temperature, which was then extracted with ethyl acetate. The organic layer was washed with water and saturated aqueous sodium chloride, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under a reduced pressure. The residue was purified by NH silica gel column chromatography (heptane:ethyl acetate=4:1-2:1) to obtain the title compound (55 mg, 18percent).1H-NMR Spectrum (CDCl3) delta (ppm): 0.91-0.94 (3H, m), 1.31-1.40 (2H, m), 1.55-1.63 (2H, m), 2.57-2.61 (2H, m), 4.03 (2H, s), 5.53 (2H, brs), 6.26 (1H, s), 6.70-6.73 (1H, m), 7.14-7.20 (4H, m), 7.71-7.73 (1H, m), 8.11-8.13 (1H, m).

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 67346-74-1, 3-Ethynylpyridin-2-amine.

Reference:
Patent; Tanaka, Keigo; Yamamoto, Eiichi; Watanabe, Naoaki; US2009/82403; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 67515-76-8, Methyl 5-aminopicolinate, 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, HPLC of Formula: C7H8N2O2, blongs to pyridine-derivatives compound. HPLC of Formula: C7H8N2O2

EXAMPLE 21 Following the procedure of Example 1, but substituting an equivalent amount of methyl 5-amino-picolinate for methyl 2-amino-nicotinate and using pyridine as solvent, maintaining the reaction mixture at 40 C. for seven hours, using methylene chloride as eluent for the chromatography column, methyl 5-(2-acetylthiomethyl-propionamido)-picolinate; m.p. 169-171 C., from ethyl acetate.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,67515-76-8, Methyl 5-aminopicolinate, and friends who are interested can also refer to it.

Reference:
Patent; Simes, Societa Italiana Medicinalle Sintetici; US4528296; (1985); 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. 58553-48-3, name is 5-(Hydroxymethyl)picolinonitrile. A new synthetic method of this compound is introduced below., category: pyridine-derivatives

Step 2: (0590) To a solution of 5-(hydroxymethyl)picolinonitrile (1.59 g, 11.9 mmol) in 80 mL of DCM was added diisopropylethylamine (3.2 mL), followed by a solution of methanesulfonyl chloride (1.49g, 13.0 mmol) in 20 mL of DCM at 0 C. The solution was stirred at 0 C. for 40 min and washed with 5% citric acid, sat. NaHCO3 (aq.) and brine. After concentration, the residue was purified by silica gel chromatography (elution with 0-30% EtOAc/Hex) to afford (6-cyanopyridin-3-yl)methyl methanesulfonate (2.33 g).

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, 58553-48-3, 5-(Hydroxymethyl)picolinonitrile.

Reference:
Patent; MERCK SHARP & DOHME CORP.; Scott, Jack D.; Stamford, Andrew W.; Gilbert, Eric J.; Cumming, Jared N.; Iserloh, Ulrich; Misiaszek, Jeffrey A.; Li, Guoqing; US2015/307465; (2015); 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.5349-17-7, name is 2-Bromo-1-(pyridin-4-yl)ethanone hydrobromide, molecular formula is C7H7Br2NO, molecular weight is 280.9446, as common compound, the synthetic route is as follows.Application In Synthesis of 2-Bromo-1-(pyridin-4-yl)ethanone hydrobromide

[0342] l-(4-{[4-(4-Pyridinyl)-l,3-thiazol-2-yl]amino}phenyl)ethanone (131). A mixture of bromoketone hydrobromide 1 (0.60 g, 2.14 mmol) and 4- acetylphenylthiourea (130) (0.41 g, 2.14 mmol) in EtOH (20 mL) was stirred at reflux temperature for 3 h. The mixture was cooled to 20 0C, diluted with water (50 mL), the pH adjusted to ca. 8 with aqueous NH3 and the mixture stirred at 20 0C for 2 h. The precipitate was filtered, washed with water (5 mL) and dried. The crude solid was purified by column chromatography, eluting with 50% EtO Ac/pet, ether, to give amine 131 (0.40 g, 64%) as a cream powder: mp (EtO Ac/pet, ether) 229-231 0C; 1H NMR delta 10.80 (br s, 1 H, NH), 8.63 (dd, J= 4.5, 1.6 Hz, 2 H, H- 2″‘, H-6′”), 8.01 (br d, J= 8.8 Hz, 2 H, H-2′, H-6’), 7.89 (dd, J= 4.5, 1.6 Hz, 2 H, H-3″‘, H-5″‘), 7.85 (br d, J= 8.8 Hz, 2 H, H-3′, H-5’), 7.82 (s, 1 H, H-5″), 2.53 (s, 3 H, H-2); 13C NMR delta 195.9, 162.5, 150.1 (2), 147.7, 144.8, 140.7, 129.8 (2), 119.8 (2), 116.0 (2), 108.7, 26.1, one carbon not observed. Anal, calcd for Ci6Hi3N3OS: C, 65.06; H, 4.44; N, 14.23. Found: C, 65.11; H, 4.40; N, 14.13%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,5349-17-7, 2-Bromo-1-(pyridin-4-yl)ethanone hydrobromide, and friends who are interested can also refer to it.

Reference:
Patent; THE BOARD OF TRUSTEES OF THE LELAND STANFORD JUNIOR UNIVERSITY; AUCKLAND UNISERVICES LIMITED; WO2009/114552; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 893423-62-6, tert-Butyl (2-chloro-3-formylpyridin-4-yl)carbamate, 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, 893423-62-6, blongs to pyridine-derivatives compound. Application In Synthesis of tert-Butyl (2-chloro-3-formylpyridin-4-yl)carbamate

4-Amino-2-chloronicotinaldehyde (1-5c) Trifluoroacetic acid (17.4 mL, 234 mmol) was added carefully to a stirred mixture of Boc aldehyde 1-4 (20 g, 78.1 mmol) and dichloromethane (60 mL) keeping the temperature below 25 C. The solution was warmed to 35 C., aged overnight (vigorous off-gassing) and then cooled to room temperature. 25 mL of MTBE was added and the resulting white slurry was aged for one hour, filtered, and the filter cake rinsed with MTBE (10 mL*2). Solid 1-5c TFA salt was dried under vacuum.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,893423-62-6, its application will become more common.

Reference:
Patent; Kelly, Michael J.; Layton, Mark E.; Sanderson, Philip E.; US2008/161317; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 18699-87-1, 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 18699-87-1 as follows.

3-Nitro-2-pyridinecarbaldehyde; 2-Methyl-3-nitropyridine (24 g, 173.91 mmol) was dissolved in 1,4-dioxane (500 mL) and to the mixture was added selenium dioxide (23 g, 208.7 mmol) and the mixture was heated under reflux for 16 h. After completion of reaction, the mixture was cooled to rt and filtered through Celite and the filtrate was concentrated under reduced pressure to give thick oily mass. The oily mass was purified by silical gel column chromatography using 20% of ethyl acetate and hexane as eluent to give 3-nitro-2-pyridinecarbaldehyde as an off white solid: 1H-NMR (CDCl3) delta: 7.7 (m, 1H), 8.3 (d, 1H), 9.0 (d, 1H), 10.3 (s, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,18699-87-1, its application will become more common.

Reference:
Patent; AMGEN INC.; US2011/152296; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem