Category: pyridine-derivatives

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. 69950-65-8, name is Methyl 6-formyl-2-pyridinecarboxylate. A new synthetic method of this compound is introduced below., Safety of Methyl 6-formyl-2-pyridinecarboxylate

General procedure: A solutionof 3 mmol of pyridine-2-carbaldehyde 2a-2c in 25 mLof glacial acetic acid was added to a solution of 3 mmol of isonitrosoacetophenone hydrazone 1a-1d in 25 mL of glacial acetic acid. The mixture was kept for 10 h at room temperature and was then refluxed for 5 min. The solvent was removed under reduced pressure, the residue was treated with ethanol, and the precipitate was filtered off, washed with ethanol, dried,and recrystallized from ethanol.

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, 69950-65-8, Methyl 6-formyl-2-pyridinecarboxylate.

Reference:
Article; Shabunina; Starnovskaya; Shtaits, Ya. K.; Kopchuk; Kovalev; Zyryanov; Rusinov; Chupakhin; Russian Journal of Organic Chemistry; vol. 54; 10; (2018); p. 1576 – 1578; Zh. Org. Khim.; vol. 54; 10; (2018); p. 1561 – 1563,3;,
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.176690-44-1, name is 2-(Pyridin-3-yl)benzaldehyde, molecular formula is C12H9NO, molecular weight is 183.21, as common compound, the synthetic route is as follows.Recommanded Product: 2-(Pyridin-3-yl)benzaldehyde

To a solution of 2-pyridin-3-yl-benzaldehyde (1 g, 5.46 mmole) in methanol (10 ml) was added a solution of NaBH4 (0.26 g, 6.82 mmole) in methanol (10 ml) at 0 C and stirred for 30 min at same temperature and then refluxed for 1 h. The unreacted NaBH4 was decomposed by solution of 6N HCI. The solvent was removed under reduced pressure and the residue was dissolved in 5N NaOH (20 ml) and extracted with ethyl acetate (3X20 ml). Combined organic extracts were dried (Na2S04), filtered and concentrated to yield 0.95 g (94%) of product. MS (ESI+) m/z 186 (M+H) +.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,176690-44-1, 2-(Pyridin-3-yl)benzaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; ABBOTT LABORATORIES; LI, Tongmei; WO2005/111003; (2005); 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. 68325-15-5, name is 3-Chloro-4-cyanopyridine. This compound has unique chemical properties. The synthetic route is as follows. SDS of cas: 68325-15-5

(b) 3-Ethoxy-4-cyanopyridine A mixture of sodium metal (1.4 g, 0.06 mol) and ethanol (10 ml) was stirred until all of the sodium metal had dissolved and the solvent was removed in vacuo. The residue was placed under argon, and DMF (50 ml), followed by 3-chloro-4-cyanopyridine (6.95 g, 0.05 mol) were added at 5 C. The mixture was warmed to room temperature and stirred for 24 hours. The solvent was removed in vacuo and the residue was treated with dichloromethane and filtered. The filtrate was removed in vacuo, the residue was treated with water and a solid was collected by filtration to afford 4.6 g (62%) of 3-ethoxy-4-cyanopyridine as a tan solid, m.p. 56-57 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, 68325-15-5, 3-Chloro-4-cyanopyridine.

Reference:
Patent; Sterling Winthrop Inc.; US5294612; (1994); 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. 620-08-6, name is 4-Methoxypyridine. A new synthetic method of this compound is introduced below., Computed Properties of C6H7NO

a) Preparation of Intermediate 21 Di-tert-butyl dicarbonate (58.333 mmol) was added portionwise under a N2 atmosphere and with rapid stirring to a solution of 4-methoxypyridine (58.333 mmol) in THF (60 ml). The mixture was cooled to 0 C., vinylmagnesium bromide (70 mmol) was added dropwise and the mixture was stirred for 3 hours at room temperature. HCl (1N) (about 150 ml) was added at 5 C. (ambient temperature of 25 C.) and the mixture was stirred for 10 minutes. The mixture was extracted with EtOAc. The organic layer was washed with 10% aqueous NaHCO3 solution then brine, dried over MgSO4, filtered and evaporated to dryness, yielding 10.7 g (82.1%) of intermediate 21.

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, 620-08-6, 4-Methoxypyridine.

Reference:
Patent; Guillemont, Jerome Emile Georges; Motte, Magali Madeleine Simone; Lancois, David Francis Alain; Thomas, Sebastein Robert Gaston; Balemans, Wendy Mia Albert; US2015/51244; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 504-29-0, 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 504-29-0, name is Pyridin-2-amine. This compound has unique chemical properties. The synthetic route is as follows.

Manufacturing Example 1-2-1: 2,2-Dimethyl-N-pyridin-2-yl-propionamide To a methylene chloride (500 mL) solution of 2-aminopyridine (50 g) were added triethylamine (81 mL) and pivaloyl chloride (72 mL) at 0C, which was stirred for 4 hours and 30 minutes at room temperature. Water was added to the reaction solution, and then extraction was performed with methylene chloride. The organic layer was washed with water and saturated brine, and dried over anhydrous magnesium sulfate and filtered, and then the filtrate was concentrated under a reduced pressure. Potassium carbonate (73 g) was added at 0C to a methanol (300 mL) solution of the residue thus obtained, which was stirred for 90 minutes at room temperature. Water was added to the reaction solution, and then extraction was performed with ethyl acetate. The organic layer was washed with saturated brine, then dried over anhydrous magnesium sulfate, and filtered, after which the filtrate was concentrated under a reduced pressure. Heptane (300 mL) was added to the residue, and the precipitated solids were filtered off to obtain the titled compound (80 g). The filtrate was then further concentrated under a reduced pressure, and the residue was purified by silica gel column chromatography (heptane:ethyl acetate = 2:1) to obtain the titled compound (12 g). 1H-NMR spectrum (DMSO-d6) delta (ppm): 1.22 (9H, s), 7.06-7.09 (1H, m), 7.72-7.77 (1 H, m), 8.01-8.03 (1 H, m), 8.29-8.31 (1 H, m), 9.71 (1 H, s).

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 504-29-0, Pyridin-2-amine.

Reference:
Patent; Eisai R&D Management Co., Ltd.; EP2065377; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 13362-26-0 ,Some common heterocyclic compound, 13362-26-0, molecular formula is C8H10N2O2, 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 13 Synthesis of ethyl 2-ethoxycarbonyl-imidazo[1,2-a]pyridine-8-carboxylate (Compound No. 1-123) A mixture of ethyl bromopyruvate (2.3 g, 10.2 m mol and ethyl 2-aminonicotinate (1.7 g, 10 m mol) in methyl ethyl ketone (17 ml) was refluxed for 5 hours. After completion of the reaction, the mixture was cooled to room temperature and distilled under reduced pressure to remove the solvent. The residue to which saturated sodium hydrogen carbonate aqueous solution (50 ml) was added was extracted with chloroform (100 ml*3). The extract was washed with water, dried over MgSO4 and concentrated under reduced pressure. The concentrate was purified by silica gel column chromatography (eluent: ethyl acetate) to give the object compound (0.7 g, yield 26.7%) as crystals. m.p. 97 C.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,13362-26-0, its application will become more common.

Reference:
Patent; Takeda Chemical Industries, Ltd.; US5498774; (1996); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 119830-47-6 ,Some common heterocyclic compound, 119830-47-6, molecular formula is C8H10N2O2, 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 5 Preparation of 5-(2-(2-chloro-4-fluorophenoxy)-6-(trifluoromethyl)benzamido)picolinic acid (74) [embedded image] To a solution of 2-chloro-4-fluoro-phenol (20.97 g, 143.10 mmol) and 2-fluoro-6-(trifluoromethyl)benzaldehyde (25 g, 130.1 mmol) in DMF (125.0 mL) was added Cs2CO3 (46.62 g, 143.1 mmol) and the reaction mixture was stirred at 100 C. for 1 hour. The reaction mixture was poured into water (500 ml) and extracted with ethyl acetate (3150 ml). The organics were combined, washed with water, brine (2), dried over Na2SO4, filtered and evaporated to give a red oil which solidified after standing over night. The material was then triturated with hot hexanes and cooled to 25 C. The slurry was filtered and washed with cold hexanes to give 2-(2-chloro-4-fluoro-phenoxy)-6-(trifluoromethyl)benzaldehyde (32.7 g, 79%) as an off white solid. 1H NMR (400 MHz, DMSO) – 10.61 (s, 1H), 7.84-7.70 (m, 2H), 7.66 (d, J=7.9 Hz, 1H), 7.47 (dd, J=9.0, 5.3 Hz, 1H), 7.42-7.32 (m, 1H), 7.12 (d, J=8.3 Hz, 1H) ppm.To a solution of 2-(2-chloro-4-fluoro-phenoxy)-6-(trifluoromethyl)benzaldehyde (31 g, 97.29 mmol) in tBuOH (155.0 mL), water (100.8 mL), CH3CN (155.0 mL) and 2-methyl-2-butene (51.45 mL, 486.4 mmol) was added sodium dihydrogen phosphate (35.02 g, 291.9 mmol) and the mixture was cooled to 0 C. Sodium chlorite (26.40 g, 291.9 mmol) was added in one portion and the mixture was stirred at 25 C. for 1 hour. The pH of the reaction was adjusted to 2-3 with 1N HCl and the layers were separated. The aqueous layer was extracted with EtOAc (3). All the organic layers were combined, and solid sodium sulfite (-5 g) was added followed by brine (50 ml) and 1N NaOH (10 ml) and the mixture was shaken until the yellow color disappeared. The layers were separated and the organic was washed with brine, dried over Na2SO4, filtered through a short plug of silica and evaporated to dryness to give 2-(2-chloro-4-fluoro-phenoxy)-6-(trifluoromethyl)benzoic acid (40 g, 98%) as an oil that was used in the next step without further purification. ESI-MS m/z calc. 334.00. found 335.1 (M+1)+. Retention time: 1.58 minutes (3 minutes run).A solution of 2-(2-chloro-4-fluoro-phenoxy)-6-(trifluoromethyl)benzoic acid (33.46 mg, 0.10 mmol), ethyl 5-aminopyridine-2-carboxylate (19.94 mg, 0.12 mmol), HATU (41.83 mg, 0.11 mmol) and N-methylmorpholine (21.99 -L, 0.20 mmol) was stirred at 100 C. for 8 hours. NaH (16.00 mg, 0.40 mmol) was added and the mixture was stirred at 100 C. for 10 min. The mixture was filtered and purified by reverse phase HPLC using a gradient of acetonitrile in Water (1-99%) and HCl as a modifier, to give 5-[[2-(2-chloro-4-fluoro-phenoxy)-6-(trifluoromethyl)benzoyl]amino]pyridine-2-carboxylic acid (74) (2.52 mg, 5%) as a white solid. ESI-MS m/z calc. 454.03. found 455.3 (M+1)+. Retention time: 1.42 minutes (3 minutes run).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,119830-47-6, its application will become more common.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; Hadida-Ruah, Sara Sabina; Anderson, Corey; Arumugam, Vijayalaksmi; Asgian, Iuliana Luci; Bear, Brian Richard; Termin, Andreas P.; Johnson, James Philip; US2014/221435; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 131803-48-0, Methyl 6-(bromomethyl)nicotinate, 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, 131803-48-0, blongs to pyridine-derivatives compound. COA of Formula: C8H8BrNO2

Example II (0492) 6-{[Bis(pyrazin-2-yl)amino]methyl}-N-hydroxypyridine-3-carboxamide (0493) (0494) II (0495) NaH (60%, 48.5mg, 1.21 mmol) was added to a solution of (3) (200mg, 1.15mmol) in DMF (7ml_) at 5C under N2(g). The reaction mixture was stirred for 20min then methyl 6-(bromomethyl)pyridine-3-carboxylate (345mg, 1.5mmol) was added as a solution in DMF (3ml_). The stirring was continued at 70C for 1 h. Reaction cooled to rt and poured onto water (100ml_). Brine (25ml_) was added and the aqueous was extracted with EtOAc (2 x 100ml_). Combined organics were dried over Na2S04, filtered and concentrated in vacuo. The residue was purified by flash column chromatography with CH2CI2/EtOAc (1 :0-0:1) then EtOAc/MeOH (1 :0-4: 1) to give (4) (129mg, 35%). (0496) 1 H NMR (500 MHz, Chloroform-d), deltaEta ppm: 9.04-9.13 (m, 1 H), 8.70 (s, 2H), 8.19 (s, 2H), 8.13 (dd, J=5.6, 2.3 Hz, 3H), 7.32 (d, J=8.2 Hz, 1 H), 5.55 (s, 2H), 3.86 (s, 3H). LCMS (ES): Found 322.9 [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,131803-48-0, its application will become more common.

Reference:
Patent; KARUS THERAPEUTICS LTD; SHUTTLEWORTH, Stephen Joseph; WHALE, Andrew David; COLMAN, Lucy Mary; ROGERS, Helen Louise; (117 pag.)WO2017/208032; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 6345-27-3 , The common heterocyclic compound, 6345-27-3, name is Isonicotinimidamide hydrochloride, molecular formula is C6H8ClN3, 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.

Isonicotinamidine hydrochloride (5.0Og, 31.7mmol) and acetaldehyde dimethylacetal (8.44mL, 63.5mmol) were combined and heated to 1100C in anhydrous DMF (35mL) in the presence of DBU (14.2OmL, 95.2mmol) for 3h. The reaction mixture was cooled to 200C, then stirred for 16h, before being concentrated in vacuo. The residue was partitioned between H2O(10OmL) and EtOAc (10OmL). The aqueous layer was extracted with EtOAc (2x50mL), then the combined organics were washed with brine (5OmL), dried (MgSO4), filtered and concentrated under reduced pressure. Flash column chromatography (EtOAc) of the residue gave 4-methyl-2-pyridin-4-yl-pyrimidine: deltaH ((CDj)2SO): 2.57 (3H, s), 7.45 (IH, d), 8.21-8.26 (2H, m), 8.72-8.77 (2H, m), 8.82 (IH, d). To a solution of this compound (1.06g, 6.17mmol) in anhydrous dioxane (2OmL) was added SeO2 (2.05g, 18.51mol), then the mixture was heated to reflux for 9Oh. The reaction mixture was cooled to 200C then filtered, washing with EtOAc. The filtrate was evaporated to dryness, then the residue was suspended in CH2Cl2. The suspension was filtered, washing with CH2Cl2, then the filtrate was evaporated to dryness to furnish the title compound: deltaH (CDCl3): 7.80 (IH, d), 8.38 (2H, d), 8.83 (2H, d), 9.13 (IH, d),10.15 (IH, s).

The synthetic route of 6345-27-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PROSIDION LTD.; WO2006/70208; (2006); 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.15128-82-2, name is 2-Nitropyridin-3-ol, molecular formula is C5H4N2O3, molecular weight is 140.1, as common compound, the synthetic route is as follows.name: 2-Nitropyridin-3-ol

(Example 2 Synthesis of Compounds I-113 and 1-144) [Show Image]Step 1 A solution of 2-nitropyridin-3-ol (6) (16.0 g, 114 mmol) in dimethylformamide (120 mL) was cooled to 0C, and then N-bromosuccinimide (26.4 g, 1.48 mmol) was gradually added thereto. The solution was then stirred at 0 C for 1 hour, and at room temperature for another 2 hours. The reaction solution was concentrated in vacuo, and then the residue was washed with diethyl ether. The filtrate was poured to aqueous saturated sodium bicarbonate, followed by extraction with diethyl ether. The organic layer was washed sequentially with water and saturated brine, then dried with anhydrous magnesium sulfate, and concentrated in vacuo to yield the subject compound (7) (15.5 g, 62%) as a white powder.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,15128-82-2, 2-Nitropyridin-3-ol, and friends who are interested can also refer to it.

Reference:
Patent; Shionogi & Co., Ltd.; EP2341052; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem