Day: August 16, 2021

Electric Literature of 524955-09-7, 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. 524955-09-7, name is 3-Chloro-4-(pyridin-2-ylmethoxy)aniline. A new synthetic method of this compound is introduced below.

Step C: [3-chloro-4-(2-pyridylmetoxyl)-phenyl]-(6-iodo-quinazolin- 4-yl)-aminehydrochloride salt (compound 8.3).[0126] 470mg of compound 8.3 (2 mmol) and 580mg of 4-chloro-6-iodo-quinazoline (2 mmol) were dissolved in isopropanol (10 ml). The reaction mixture was refluxed for 12 hours. The solid product was collected by filtration, washed with cold isopropanol (10 mL) and ether (20 mL), and air dried to afford 450 mg of the clean desired material.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,524955-09-7, 3-Chloro-4-(pyridin-2-ylmethoxy)aniline, and friends who are interested can also refer to it.

Reference:
Patent; KANIONUSA INC.; SHEN, Wang; ZHANG, Aimin; FAN, Junfa; ZHENG, Xiaoling; WO2011/2523; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1211540-92-9 , The common heterocyclic compound, 1211540-92-9, name is 3-Bromo-4-chloro-5-fluoropyridine, molecular formula is C5H2BrClFN, 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.

Compound (VII-17) (100 mg, 0.475 mmol),Compound (VIa-2) (146 mg, 0.523 mmol),(A-taPhos) 2 PdCl2 (16.8 mg, 0.0240 mmol)And cesium carbonate (310 mg, 0.950 mmol)Was dissolved in 1,4-dioxane (1.5 mL) and water (0.30 mL)Dissolved in the mixture, under microwave irradiation,And the mixture was stirred at 70 C. for 10 minutes.Water was added to the reaction solution,And extracted with chloroform.The solvent was distilled off under reduced pressure,The residue was purified by silica gel column chromatography (NH silica gel, n-hexane: ethyl acetate = 97: 3 ? 75: 25)Compound (I-97)(Yield 138 mg, Yield 79%)As a colorless oil.

The synthetic route of 1211540-92-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Kaken Pharmaceutical Co., Ltd.; Watanabe, Atsushi; Sato, Yuki; ogura, Keiji Tamada; Tatsumi, Yoshiyuki; (283 pag.)JP2018/145180; (2018); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1008-91-9, Adding some certain compound to certain chemical reactions, such as: 1008-91-9, name is 1-(Pyridin-4-yl)piperazine,molecular formula is C9H13N3, 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 1008-91-9.

General procedure: 2-(7-Aza-1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (HATU; 1.2 equivalents) was added to a solution of the corresponding alpha-methyl carboxylic acid (2) (1 equiv), the appropriate amine (1.5 equiv) and DIEA (2 equiv) in dry acetonitrile (10 mL) at room temperature under argon atmosphere. The reaction mixture was stirred at room temperature overnight. Solvent was evaporated under reduced pressure, and the crude product was purified using a Teledyne Isco Combiflash Rf purification machine using 0-10% CHCl3/methanol as eluent to provide the desired amides 3-59 in 68-95% yields.

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. 1008-91-9, 1-(Pyridin-4-yl)piperazine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Mathew, Bini; Snowden, Timothy S.; Connelly, Michele C.; Guy, R. Kiplin; Reynolds, Robert C.; Bioorganic and Medicinal Chemistry Letters; vol. 28; 12; (2018); p. 2136 – 2142;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 55676-21-6, 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 55676-21-6, name is 1-(2-Chloropyridin-3-yl)ethanone. This compound has unique chemical properties. The synthetic route is as follows.

A solution of 1-(2-chloropyridin-3-yl)ethanone (B-2) (6 g, 38.6 mmol) and hydrazine (85%, 9.1 g, 154.4 mmol) in pyridine (80 mL) was stirred under reflux overnight. The mixture was cooled to room temperature, concentrated, diluted with water (80 mL) and then extracted with ethyl acetate (100 mL*3). The combined organic layers were washed with brine, dried over Na2S04, and concentrated under vacuo. The resulting residue was used for the next step without furtuer purification. MS (m/z): 134 (M+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 55676-21-6, 1-(2-Chloropyridin-3-yl)ethanone.

Reference:
Patent; HUTCHISON MEDIPHARMA LIMITED; SU, Wei-Guo; JIA, Hong; DAI, Guangxiu; WO2011/79804; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 10165-86-3 , The common heterocyclic compound, 10165-86-3, name is Methyl 6-formylnicotinate, molecular formula is C8H7NO3, 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.

Example 151C methyl 6-[(1S,3E)-3-[4-(difluoromethoxy)-2-hydroxyphenyl]-1-hydroxy-3-{[(S)-2-methylpropane-2-sulfinyl]imino}propyl]pyridine-3-carboxylate A solution of diisopropylamine (280 muL, 1.965 mmol) in tetrahydrofuran (8 mL) was cooled to 0° C., treated dropwise with 2.5 M n-butyllithium in hexanes (720 muL, 1.801 mmol), stirred at 0° C. for 30 minutes, cooled to -78° C., treated dropwise with a solution of Example 151B (687 mg, 1.637 mmol) in tetrahydrofuran (4 mL), stirred at -78° C. for 45 minutes, treated dropwise with a solution of methyl 6-formylnicotinate (270 mg, 1.637 mmol) in tetrahydrofuran (4 mL), stirred at -78° C. for 1 hour, allowed to warm to -10° C. for 1 hour, treated dropwise with a solution of acetic acid (281 muL, 4.91 mmol) in tetrahydrofuran (1 mL) and partitioned between ethyl acetate (30 mL) and saturated NaHCO3 solution (5 mL). The ethyl acetate layer was washed with brine, dried (MgSO4), filtered, and concentrated. The residue was chromatographed on silica gel, eluting with a gradient of 15percent 100percent ethyl acetate in heptanes to provide products that contained the silyl protecting group (first eluting), followed by the title compound that eluted later. The fractions containing the silyl protecting group were combined, concentrated to dryness, dissolved in tetrahydrofuran (10 mL) under N2, cooled to 0° C., treated with 1 M tetra-n-butylammonium fluoride in tetrahydrofuran (1637 mul, 1.637 mmol) and stirred at 0° C. for 1 hour. The mixture was partitioned between methyl tert-butyl ether (50 mL) and 5percent citric acid solution (25 mL). The methyl tert-butyl ether layer was washed with brine, dried (MgSO4), filtered, and concentrated. The residue was chromatographed on silica gel, eluting with a gradient of 15percent to 100percent ethyl acetate in heptanes to provide more of the title compound. The two portions of title compound were combined to provide 192 mg of title compound. 1H NMR (501 MHz, CDCl3) delta 13.00 (s, 1H), 9.18 (d, J=1.6 Hz, 1H), 8.22 (dd, J=8.2, 2.1 Hz, 1H), 7.58 (d, J=8.2 Hz, 1H), 7.54 (d, J=9.1 Hz, 1H), 6.63 (d, J=2.4 Hz, 1H), 6.54 (t, J=73.1 Hz, 1H), 6.47 (dd, J=9.0, 2.5 Hz, 1H), 5.33 (q, J=5.3 Hz, 1H), 4.90 (d, J=5.3 Hz, 1H), 3.96 (s, 3H), 3.80-3.74 (m, 2H), 1.40 (s, 9H); LC/MS (ESI+) m/z 471 (M+H)+.

The synthetic route of 10165-86-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AbbVie S.a.r.l.; Galapagos NV; Altenbach, Robert J.; Bogdan, Andrew; Cowart, Marlon D.; Esmieu, William Ramesh; Gfesser, Gregory A.; Greszler, Stephen N.; Koenig, John R.; Kym, Philip R.; Liu, Bo; Malagu, Karine Fabienne; Patel, Sachin V.; Scanio, Marc J.; Searle, Xenia B.; Voight, Eric; Wang, Xeuqing; Yeung, Ming C.; (202 pag.)US2017/15675; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 5470-22-4, 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 5470-22-4 as follows.

Compound 5 was prepared according to a modified procedure (WO2013/057253). To a suspension of the commercially available 4-chloro-pyridine-2-carboxylic acid 4 (5.0 g, 31.84 mmol) in dichloromethane (135 ml) at 0 C was added oxalyl chloride (4.8 g, 38.21 mmol), followed by a slow addition of catalytic amount of dimethylformamide (0.55 ml). The resulting mixture was stirred at room temperature for 2 h. After this time, the mixture was concentrated to dryness under reduced pressure. The solid residue was solubilized in methanol (55 ml) and was stirred at room temperature for another 16 h. The mixture was concentrated to dryness under reduced pressure, and the residue re-suspended with 5% aq. NaHCC>3. The product was extracted with EtOAc (2 x 20 ml). The combined organic layer was washed with brine (2 chi 10 ml), dried over anhydrous MgS04, filtered and concentrated to dryness under reduced pressure to afford 5 (4.0 g, 74%) as a beige solid. XH N MR (300 M Hz, CDCI3): delta 8.63 (d, J = 5.0 Hz, 1H), 8.12 (dd, J = 2.0, 0.5 Hz, 1H), 7.48 (dd, J = 5.0, 2.0 Hz, 1H), 4.00 (s, 3H). 13C N MR (75 MHz, CDCI3): delta 164.7, 150.7, 149.3, 145.5, 127.2, 125.7, 53.3. HRMS (APPI) calcd. for C7H7CI N02+ [M+H]+ 172.0160, found: 172.0156.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,5470-22-4, its application will become more common.

Reference:
Patent; CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE; INSTITUT CURIE; UNIVERSITY OF TEXAS AT AUSTIN; INSTITUT NATIONAL DE LA SANTE ET DE LA RECHERCHE MEDICALE; RODRIGUEZ, Raphael; ZACHARIOUDAKIS, Emmanouil; KUNALINGAM, Lavaniya; BARTOLI, Alexandra; MILLER, Kyle; AGARWAL, Poonam; (41 pag.)WO2017/102934; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 69627-02-7, Thieno[3,2-b]pyridin-7(4H)-one, 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 C7H5NOS, blongs to pyridine-derivatives compound. Computed Properties of C7H5NOS

To a suspension of 7-[1,1-dimethyl-2-(2-trifluoromethyloxiranyl)ethyl]-5-methanesulfonyl-2,3-dihydrobenzofuran (100 mg) and thieno[3,2-b]pyridin-7-ol (82.9 mg) in 0.75 mL of anhydrous ethanol was added sodium ethoxide (21 wt. % solution in ethanol, 102 muL). After heating at 85 C. for 16 hours, the reaction mixture was diluted with ethyl acetate, dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography with silica gel (eluted with 4% methanol-methylene chloride) to give the title compound as a pale yellow solid (108 mg), m.p. 163 C.-165 C.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,69627-02-7, Thieno[3,2-b]pyridin-7(4H)-one, and friends who are interested can also refer to it.

Reference:
Patent; Boehringer Ingelheim Pharmaceuticals, Inc.; US2005/234091; (2005); 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.113975-22-7, name is 2-Fluoro-3-iodopyridine, molecular formula is C5H3FIN, molecular weight is 222.99, as common compound, the synthetic route is as follows.category: pyridine-derivatives

To a solution of diisopropylamine (345 mL, 249 g, 2.46 mol) in anhydrous THF (5 L) at -8 to -10 C. under a blanket of N2 was added n-BuLi (880 mL, 158 g, 2.46 mol) dropwise via cannula. The mixture was stirred at -10 C. for 30 min, cooled to -78 C. and treated with a solution of 2-fluoro-3-iodopyridine (500 g, 2.24 mol) in dry THF (2 L) dropwise. After the addition, the reaction mixture was warmed to -60 C. and this temperature was maintained for 2 h. The mixture was then cooled to -78 C., treated with ethyl formate (183 g, 2.47 mol) dropwise, followed by sodium methoxide (149 g, 2.75 mol) in MeOH (1.5 L) and warmed to ambient temperature. The reaction mixture was quenched with ice water and extracted with EtOAc. The layers were separated and the organic phase was washed with water and brine, dried (Na2SO4) and concentrated in vacuo. The residue was purified by flash chromatography on silica gel to afford 4-iodo-2-methoxynicotinaldehyde (380 g, 64%) as a solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,113975-22-7, 2-Fluoro-3-iodopyridine, and friends who are interested can also refer to it.

Reference:
Patent; Bristol-Myers Squibb Company; US2008/114033; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 136117-74-3, Imidazo[1,2-a]pyridine-8-carbaldehyde, 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, 136117-74-3, blongs to pyridine-derivatives compound. Formula: C8H6N2O

[0167] To a solution of dimethyl 3-oxo-l ,3-dihydroisobenzofuran-l-ylphosphonate (610 mg, 2.4 mmol), imidazo[l,2-a]pyridine-8-carbaldehyde (350 mg, 2.4 mmol, lequiv.) in THF ( 5 mL) was added Et3N (0.33 mL 2.4 mmol). The mixture was stirred at rt for 48 h. The precipitation was filtered off and washed with EtOAc. The filtrate was concentrated to give 3-(imidazo[l,2-a]pyridin-8-ylmethylene)isobenzofuran-l(3H)-one(400 mg, 64%>) as a yellow solid. Small crude sample (-20 mg ) was purified on RP-HPLC with CCN and water as eluent to separated the E/Z isomers (10 mg, 7 mg). NMR(400 MHz, CD3OD) Z-form: delta= 8.52 (d, 1 H), 7.95-7.91 (m, 2 H), 7.62-7.54 (m, 4 H), 7.52-7.48 (m, 1 H), 7.09 (s, 1 H), 7.04 (t, 1 H) E-form: delta= 8.38 (d, 1 H), 8.15 (d, H), 8.05 (d, 1 H), 7.95 (d, 1 H), 7.90-7.84 (m, 2 H), 7.67 (t, 1 H), 7.64 (s, 1 H), 7.33 (s, 1 H), delta 7.05 (t, 1 H). LRMS (M+H+) m/z 263.1

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,136117-74-3, its application will become more common.

Reference:
Patent; GLOBAL BLOOD THERAPEUTICS, INC.; CYTOKINETICS, INC.; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; METCALF, Brian; CHUANG, Chihyuan; WARRINGTON, Jeffrey; PAULVANNAN, Kumar; JACOBSON, Matthew P.; HUA, Lan; MORGAN, Bradley; WO2013/102142; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 105170-27-2, Adding some certain compound to certain chemical reactions, such as: 105170-27-2, name is 2-Bromo-5-methoxypyridine,molecular formula is C6H6BrNO, 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 105170-27-2.

Example 287A [1-(3,4-dichlorophenyl)cyclobutyl](5-methoxypyridin-2-yl)methanone A solution of 2.5M n-Butyl lithium (6.5 mL, 16.25 mmol) in hexanes plus anhydrous diethyl ether (50 mL) was chilled to -75 C., followed by the dropwise addition of 2-bromo-5-methoxypyridine (3.12 g, 16.59 mmol) in diethyl ether (5 mL). The brown solution was stirred for 1 hour, followed by the addition of 1-(3,4-dichlorophenyl)-cyclobutanecarbonitrile (3.0 g, 13.27 mmol) in diethyl ether (5 mL). The reaction was warmed to 0 C. while stirring for 2 hours. The reaction was quenched with 1N hydrochloric acid (100 mL) and the biphasic mixture was stirred for 1 hour at ambient temperature. Added 3N sodium hydroxide (100 mL) and extracted twice with EtOAc (200 mL). The combined organic phases was washed with brine, dried over Na2SO4, filtered, and concentrated. The residue was chromatographed on silica (0-100% EtOAc in heptane) to give Example 287A (4.046 g, 12.03 mmol, 91% yield) as a light yellow oil. MS (ESI+): m/z 336 (M+H). 1H NMR (500 MHz, CD3CN) delta 8.14 (d, J=2.9 Hz, 1H), 7.96 (d, J=8.8 Hz, 1H), 7.64 (d, J=2.1 Hz, 1H), 7.40 (d, J=8.3 Hz, 1H), 7.35 (dd, J=8.4, 2.1 Hz, 1H), 7.31 (dd, J=8.8, 2.9 Hz, 1H), 3.86 (s, 3H), 3.00-2.89 (m, 2H), 2.66-2.54 (m, 2H), 2.02-1.91 (m, 1H), 1.89-1.77 (m, 1H).

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. 105170-27-2, 2-Bromo-5-methoxypyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; AbbVie Inc.; Bayburt, Erol K.; Clapham, Bruce; Cox, Phil B.; Daanen, Jerome F.; Dart, Michael J.; Gfesser, Gregory A.; Gomtsyan, Arthur; Kort, Michael E.; Kym, Philip R.; Schmidt, Robert G.; Voight, Eric A.; US2013/131036; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem