Category: pyridine-derivatives

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 83664-33-9, name is 2-(Benzyloxy)-5-bromopyridine. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 2-(Benzyloxy)-5-bromopyridine

To a solution of [2-BENZYLOXY-5-BROMO-PYRIDINE] (1.64 g, 6.2 mmol) in tetrahydrofuran (25 [ML,-78C)] was added n-butyllithium (2.5 M in hexane, 2.61 mL, 1.05 equiv). After 1 h [AT-78C,] dimethylformamide (0.97 mL, 2 equiv) was added and the mixture stirred for 30 min. The reaction was quickly poured into a stirred solution of 5% aqueous sodium bicarbonate (50 [ML)] and extracted with diethyl ether [(-3X).-THE ETHEREAL-WAS WASHED-WITH BRINE, DNeD-OVER MaGNESIUM~SULFATE, AND] concentrated to give 1.16 g (quant. ) which was used without purification. Mass spec.: 186.34 [(MH)] [+.]

With the rapid development of chemical substances, we look forward to future research findings about 83664-33-9.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2003/104236; (2003); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 886365-46-4, 5-Chloro-3-methylpyridine-2-carboxylic acid, 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, Computed Properties of C7H6ClNO2, blongs to pyridine-derivatives compound. Computed Properties of C7H6ClNO2

Example 4 Synthesis of N-(3-((4S,6S)-2-amino-4-(fluoromethyl)-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-4-yl)-4-fluorophenyl)-5-chloro-3-methylpicolinamide The title compound was synthesized by procedures and steps analogous to those described in Method A in Example 2 above, but using 5-chloro-3-methylpicolinic acid (Intermediate 6) in step 1. MS m/z=463.0 [M+H]+. Calculated for C19H16ClF5N4O2: 462.801 1H NMR (400 MHz, CHLOROFORM-d) delta ppm 2.22 (t, J=13.20 Hz, 1H) 2.73 (dd, J=13.60, 2.64 Hz, 1H) 2.79 (s, 3H) 4.14-4.22 (m, 1H) 4.41-4.58 (m, 1H) 4.63-4.79 (m, 1H) 7.11 (dd, J=11.54, 9.00 Hz, 1H) 7.47 (dd, J=6.94, 2.84 Hz, 1H) 7.65 (d, J=1.76 Hz, 1H) 8.08 (ddd, J=8.85, 4.16, 2.84 Hz, 1H) 8.39 (d, J=1.76 Hz, 1H) 10.04 (s, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,886365-46-4, 5-Chloro-3-methylpyridine-2-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; MINATTI, Ana Elena; LOW, Jonathan D.; ALLEN, Jennifer R.; CHEN, Jian; CHEN, Ning; CHENG, Yuan; JUDD, Ted; LIU, Qingyian; LOPEZ, Patricia; QIAN, Wenyuan; RUMFELT, Shannon; RZASA, Robert M.; TAMAYO, Nuria A.; XUE, Qiufen; YANG, Bryant; ZHONG, Wenge; US2014/249104; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 1124-29-4, name is 5-Acetylpyridin-2(1H)-one, molecular formula is C7H7NO2, 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. HPLC of Formula: C7H7NO2

General procedure: [0561] To a solution of III-3 (1 eq.) in DCM (0.1 mmol/mL) was added boronic acid III-4 (2 eq.), Cu(OAc)2 (1 eq), Pyridine (10 eq.) and Pyridine-N-Oxide (2 eq.), followed by addition of 4 molecular sieve (quantity approx. equal to III-3). The reaction mixture was stirred at rt under oxygen atmosphere overnight. After completion of the reaction indicated by TLC, the resulting mixture was filtered and washed with, the filtrate was washed with brine, dried over Na2SO4 and concentrated. The residue was purified by column chromatography on silica gel to give III-5. [0562] Compound 10 (61% yield): 1H NMR (DMSO-d6, 400 MHz) delta 8.43 (d, J=2.4 Hz, 1H), 7.90 (dd, J=9.6, 2.4 Hz, 1H), 7.39 (d, J=8.8 Hz, 2H), 7.06 (d, J=8.8 Hz, 2H), 6.51 (d, J=9.6 Hz, 1H), 3.81 (s, 3H), 2.41 (s, 3H).

With the rapid development of chemical substances, we look forward to future research findings about 1124-29-4.

Reference:
Patent; Buckman, Brad Owen; Nicholas, John Beamond; Ramphal, Johnnie Y.; Emayan, Kumaraswamy; Seiwert, Scott D.; US2014/94456; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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 84199-61-1, name is 3-Acetyl-2-bromopyridine. This compound has unique chemical properties. The synthetic route is as follows. Formula: C7H6BrNO

General procedure: A mixture of bromide 13 (61.8 mmol), Pd(OAc)2 (140 mg, 0.624 mmol), PPh3 (0.330 g, 1.26 mmol), CuI (22 mg, 0.116 mmol), and 2-prop-2-ynyloxytetrahydropyran (14) (13.0 g, 92.8 mmol) in triethylamine (250 mL) was stirred at 80 C under an argon atmosphere for 16 h. After this period, the mixture was cooled to rt, the precipitate was filtered, and the filtrate was evaporated. The residue was dissolved in EtOAc (700 mL), the solution was washed with saturated aq NaHCO3 (2200 mL), brine (200 mL), dried over Na2SO4, and evaporated in vacuo. The crude product was purified by column chromatography (CHCl3 – MeOH (19:1) (15a-c) or hexanes – EtOAc (2:1) (15d,e) as eluent).

With the rapid development of chemical substances, we look forward to future research findings about 84199-61-1.

Reference:
Article; Subota, Andrii I.; Artamonov, Oleksiy S.; Gorlova, Alina; Volochnyuk, Dmitriy M.; Grygorenko, Oleksandr O.; Tetrahedron Letters; vol. 58; 20; (2017); p. 1989 – 1991;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 23628-31-1, 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. 23628-31-1, name is 6-Aminopicolinic acid, molecular formula is C6H6N2O2, 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.

Example 3. Preparation of 2-(4-fluoro-2-(trifluoromethyl)phenyl)-N-(6- (morpholinomethyl) pyridine-2-yl)-3H-imidazo[4,5-b]pyridine-7-carboxamide (Compound 110):; Step 1) Synthesis of ethyl 6-aminopicolinate (10): 9 10To a solution of 2-amino-6-pyridinecarboxylic acid (9; 6.0 g, 43.5 mmol) in ethanol (150 mL) was added SOCl2 (12.0 g, 101.0 mmol) at 0 0C. The resulting reaction mixture was stirred under reflux for 12 h. Upon cooling to room temperature, the reaction mixture was concentrated under reduced pressure. Enough saturated aqueous Na2CO3 solution was added to adjust the pH = 9. The mixture was concentrated under reduced pressure and dichloromethane (150 mL) was added to the resulting residue. The mixture was stirred vigorously at room temperature for 30 min and then filtered. The filtrate was concentrated under reduced pressure to afford ethyl 6-aminopicolinate 10 (5.5 g, 76%). MS (ESI) calcd for C8Hi0N2O2: 166.2; found: 167 [M+H].

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 23628-31-1, 6-Aminopicolinic acid.

Reference:
Patent; SIRTRIS PHARMACEUTICALS, INC.; VU, Chi, B.; DISCH, Jeremy, S.; WO2010/88574; (2010); 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. 76041-79-7, name is 5-Bromo-3-(trifluoromethyl)pyridin-2-ol. A new synthetic method of this compound is introduced below., HPLC of Formula: C6H3BrF3NO

To a solution of 5-bromo-3-(trifluoromethyl)-2(1H)-pyridinone (D16) (2 g) and silver carbonate (6.84 g) in toluene (25 mL) stirred in air at room temperature was added 2-iodopropane (5.79 mL) dropwise. The reaction mixture was stirred at room temperature for 1 day. The reaction mixture was filtered and the filtrate was concentrated, the residue was purified by column chromatography to give 5-bromo-2-[(1-methylethyl)oxy]-3-(trifluoromethyl)pyridine (D17) (1.2 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, 76041-79-7, 5-Bromo-3-(trifluoromethyl)pyridin-2-ol.

Reference:
Patent; GLAXO GROUP LIMITED; Lin, Xichen; Ren, Feng; Zhang, Haibo; US2013/12491; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 19235-89-3, 4-Chloropyridine-2-carbonitrile, 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: C6H3ClN2, blongs to pyridine-derivatives compound. HPLC of Formula: C6H3ClN2

To a suspension of 4-chloropyridine-2-carbonitrile (2.3 g, 16.6 mmol) in DMF (100 mL) was added cesium carbonate (16.3 g, 50.0 mmol) and 3-(4-hydroxy-phenyl)propanoic acid (3.03 g, 18.3 mmol). The reaction was heated to 50 C. for 3 days. The mixture was cooled to rt, concentrated, and then taken up in 300 mL of water. The pH was adjusted to 3 by the dropwise addition of oxalic acid and a precipitate formed. The precipitate was filtered to give the title compound as a cream solid (4.17 g, 95%). LCMS: Method FA, Rt=1.49 min, [MH+=269].

The synthetic route of 19235-89-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Millennium Pharmaceuticals, Inc.; US2006/160803; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 135900-33-3, 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.135900-33-3, name is 6-(Trifluoromethoxy)pyridin-3-amine, molecular formula is C6H5F3N2O, molecular weight is 178.11, as common compound, the synthetic route is as follows.

[0294] A stirred solution of 7-bromo-6-fluoroquinoline Int-6 (Example 123) (100 mg, 0.442 mmol), 6-(trifluoromethoxy)pyridin-3-amine (157 mg, 0.884 mmol, 2.0 eq) and Na2CC>3 (112 mg, 0.884 mmol) in dry acetonitrile (2 mL) was degassed with Argon gas in a microwave vessel for 15 min. Then Mo(CO)6 (117 mg, 0.442 mmol, 1.0 eq), T3u3PHBF4 (15.3 mg, 0.05 mmol 0.12 eq) and Pd(OAc)2 (10 mg, 0.044 mmol, 0.1 eq) were added to this mixture, and degassing was continued for additional 10 min. The reaction mixture was irradiated in microwave at 90 C for 2 hrs. The progress of the reaction was monitored by LCMS and TLC. Upon completion, the reaction mixture was concentrated in vacuo. The crude product was purified by silica gel column chromatography using 50% EtOAc in petroleum ether as eluent to give 25 mg (16% yield) of the desired compound 129 as a pale-yellow solid. 99.2 % HPLC purity at 215 nm. 1H NMR (400 MHz, CDC13): delta 9.03- 9.02 (dd, J = 4.0 Hz, 1.6 Hz, 1H), 8.97-8.99 (d, J = 7.6 Hz, 1H), 8.59 (s, 1H), 8.55 (s, 1H), 8.47-8.49 (dd, J = 8.8 Hz, 2.4 Hz, 1H), 8.45-8.46 (d, J = 2.4 Hz, 1H), 8.18 (d, J = 8.4 Hz, 1H), 7.61-7.64 (d, J = 12.8 Hz, 1H), 7.56-7.52 (dd, J = 8.4 Hz, 4.0 Hz, 1H), 7.12-7.10 (d, J = 8.0 Hz, 1H). 99.7% purity by LCMS; MS (ESI) m/z =352.14 [M+H]+.

Statistics shows that 135900-33-3 is playing an increasingly important role. we look forward to future research findings about 6-(Trifluoromethoxy)pyridin-3-amine.

Reference:
Patent; ACTAVALON, INC.; DNEPROVSKAIA, Elena, V.; HOLZWARTH, Michael, S.; RYCHNOVSKY, Scott, D.; (184 pag.)WO2018/85348; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 3430-16-8, 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.3430-16-8, name is 3-Bromo-5-methylpyridine, molecular formula is C6H6BrN, molecular weight is 172.02, as common compound, the synthetic route is as follows.

The following are successively introduced into a microwave tube: 469.80 mul (4.07 mmol) of 3-bromo-5-methylpyridine in 20 mL of H2O/DMF: (1/3: v/v), 2.03 mL (5.70 mmol) of tributyl(1-ethoxyvinyl)tin, 57.12 mg (81.38 mmol) of bis(triphenylphosphine)palladium(II) chloride, 1.12 g (8.14 mmol) of potassium carbonate. After irradiating with microwaves for 1 hour at 110 C., the reaction mixture is evaporated to dryness and the residue is taken up in water and extracted with ethyl acetate. The organic phase is dried over magnesium sulfate and evaporated to dryness. The residue is taken up in a solution consisting of 6 mL of methanol and 1 mL of 1 N hydrochloric acid. After stirring overnight at room temperature, the reaction mixture is evaporated to dryness and the residue is taken up in saturated aqueous NaHCO3 solution and extracted with ethyl acetate. The organic phase is dried over magnesium sulfate and evaporated to dryness. The residue is purified by chromatography on silica gel (eluent: 50/50 EtOAc/heptane) to give 160 mg of 1-(2-methylpyrid-3-yl)ethanone, the characteristics of which are as follows: LC/MS (method G): ESI+ [M+H]+: m/z 136 tr (min)=0.38 1H NMR (300 MHz, delta in ppm, DMSO-d6): 2.58 (s, 3H), 2.61 (s, 3H), 7.38 (m, 1H), 8.2 (m, 1H), 8.57 (m, 1H).

The chemical industry reduces the impact on the environment during synthesis 3430-16-8, I believe this compound will play a more active role in future production and life.

Reference:
Patent; El-Ahmad, Youssef; Filoche-Romme, Bruno; Ganzhorm, Axel; Marciniak, Gilbert; Muzet, Nicolas; Ronan, Baptiste; Vivet, Bertrand; Zerr, Veronique; US2015/183804; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 946002-90-0, name is (S)-1-(5-Bromopyridin-2-yl)pyrrolidin-3-ol, the common compound, a new synthetic route is introduced below. Quality Control of (S)-1-(5-Bromopyridin-2-yl)pyrrolidin-3-ol

A mixture of compound F1 (3.38 g, 13.9 mmol), 2,6-dichloro-p-cresol (3.69 g, 20.9 mmol), ADDP (5.26 g, 20.9 mmol) and PBu3 (85%, 10.3 mL, 35.4 mmol) in toluene (200 mL) was heated to reflux for 2 h. The mixture was allowed to cool to rt, and was diluted with heptane. The mixture was filtered, washed with heptane, and the filtrate was evaporated under reduced pressure. The residue was diluted with CH2Cl2, and this mixture was washed with aq. 1M NaOH (2×). The org. layer was dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (CH2Cl2/heptane 4:1?CH2Cl2) yielded the title compound (5.46 g, 98%). LC-MS: tR=0.91 min; ES+: 403.00.

The synthetic route of 946002-90-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Actelion Pharmaceuticals, Ltd.; US2009/88457; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem