Category: pyridine-derivatives

Electric Literature of 947249-13-0, 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. 947249-13-0, name is 5-Bromo-3-(difluoromethoxy)pyridin-2-amine. A new synthetic method of this compound is introduced below.

To a solution of 5-bromo-3-(difluoromethoxy)pyridin-2-amine (3.2 g, 13.39 mmol) in 1 ,4-dioxane (60 mL) were added4,4,4?,4?,5,5,5?,5?-octamethyl-2,2?-bi( 1 ,3,2-dioxaborolane) (3.74 g, 14.73 mmol),tricyclohexylphosphine (525 mg, 1.87 mmol), potassium acetate (3.28 g, 33.47 mmol) and tris(dibenzylideneacetone)dipalladium(0) (490 mg, 0.53 mmol). The reaction mixture was purged with nitrogen for 2 mm and heated to 110 C for 16 h and subsequently concentrated to dryness in vacuo. The resulting viscous mass was diluted with water and extracted with ethyl acetate (3 x 75 mL). The combined organic layers were dried over sodium sulfate andconcentrated to dryness in vacuo. The resulting residue was purified by column chromatography (silica gel, 100-200 mesh, 25% ethyl acetate in hexane) affording 3-(difluoromethoxy)-5- (4,4,5 ,5-tetramethyl- 1,3 ,2-dioxaborolan-2-yl)pyridin-2-amine (1.3 g, 34%): 1H NMR (400 MHz, DMSO-d6) oe: 8.03 (s, 1H), 7.33 (s, 1H), 7.11 (t, I = 73.6 Hz, 1H),6.44 (s, 2H), 1.25 (s, 12H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,947249-13-0, 5-Bromo-3-(difluoromethoxy)pyridin-2-amine, and friends who are interested can also refer to it.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; LYSSIKATOS, Joseph P.; LIU, Wen; SIU, Michael; ESTRADA, Anthony; PATEL, Snahel; LIANG, Guibai; HUESTIS, Malcolm; CHEN, Kevin; WO2015/91889; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 139585-48-1, 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. 139585-48-1, name is 2-Chloro-5-methoxypyridine, molecular formula is C6H6ClNO, 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.

A 100 mL round-bottom flask was charged with NiCl2*6H2O (40 mg, 0.15 mmol) and DMF (10 mL). The resulting solution was stirred and heated to 40 C. Then, 2-chloro-5-methoxypyridine (6,3 mmol), anhydrous LiCl (130 mg, 3 mmol), and zinc dust (230 mg,3.6 mmol) were added. When the temperature rose to 50 C, a grain of iodine crystal and two drops of acetic acid were added to the mixture. The mixture was stirred at 55-60 C until complete conversion of 2-halopyridine (monitored by TLC). To the cooled reaction mixture was added 1 N HCl aqueous solution (5 mL) to consume the remaining zinc dust. The resulting mixture was made alkaline with aqueous ammonia (25%) and diluted with CH2Cl2. The organic layers were collected, dried over anhydrous Na2SO4, concentrated, and purified by column chromatography on silica gel (Hexane/EtOAc 10:1, v/v) to afford desired 5,5′-dimethoxy-2,2′-bipyridine as a light yellow solid, 130 mg, 40% yield. 1H NMR (500 MHz, CDCl3): d 8.33 (d, J 3.0 Hz, 2H, ArH), 8.24 (d, J 9.0 Hz,2H, ArH), 7.30 (dd, J1 9.0 Hz and J2 3.0 Hz, 2H, ArH), 3.91 (s, 6H,2OCH3).

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 139585-48-1, 2-Chloro-5-methoxypyridine.

Reference:
Article; Xu, Bin; Gartman, Jackson A.; Tambar, Uttam K.; Tetrahedron; vol. 73; 29; (2017); p. 4150 – 4159;,
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. 153034-88-9, name is 2-Chloro-4-iodo-3-methylpyridine. A new synthetic method of this compound is introduced below., Application In Synthesis of 2-Chloro-4-iodo-3-methylpyridine

N-((S)-1-(4-((R)-1-(2-Chloro-3-methylpyridin-4-yl)pyrrolidin-3-yloxy)phenyl)ethyl)acetamide Under inert gas atmosphere 0.80 g (2.53 mmol) of example XIII.1, 0.65 g (2.53 mmol) of 2-chloro-4-iodo-3-methyl-pyridine, 1.00 g (10.4 mmol) NaOtBu and 100 mg (0.14 mmol) chloro(2-dicyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl)(2-(2-aminoethyl)-phenyl)-palladium (II) are added to 50 mL dioxane and stirred at 45 C. over night. Afterwards the solvent is removed, water is added and the product is extracted with EtOAc. The organic layer is dried over MgSO4, filtered and the solvent is removed in vacuo. The crude product is purified by HPLC (ACN/H2O/TFA). C20H24ClN3O2 (M=373.9 g/mol) ESI-MS: 374 [M+H]+Rt(HPLC):0.77 min (method M)

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, 153034-88-9, 2-Chloro-4-iodo-3-methylpyridine.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; FLECK, Martin; HEINE, Niklas; NOSSE, Bernd; ROTH, Gerald Juergen; US2014/213568; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1190320-33-2, 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.1190320-33-2, name is 6-Fluoro-1H-pyrrolo[3,2-b]pyridine, molecular formula is C7H5FN2, molecular weight is 136.13, as common compound, the synthetic route is as follows.

Step 1: 6-Fluoro-lH-pyrrolo[3,2-b]pyridine N-oxide (60) 60 [00667] To a stirred solution of compound 24 (1.2 g, 8.8 mol, 1.0 eq.) in DCM (100 mL), was added mCPBA (2.3 g, 13.2 mmol, 1.5 eq.) at room temperature. After stirring at room temperature overnight, the reaction was cooled at 0 C for lh, and then filtered to collect the solid. The solid was washed with diethyl ether, and then dried under high vacuum give compound 60 (1.3 g, 8.5 mmol, 97%) as a solid, which is used without further purification.

Statistics shows that 1190320-33-2 is playing an increasingly important role. we look forward to future research findings about 6-Fluoro-1H-pyrrolo[3,2-b]pyridine.

Reference:
Patent; AKARNA THERAPEUTICS, LTD.; MOHAN, Raju; PRATT, Benjamin, Anthony; (297 pag.)WO2016/103037; (2016); 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. 195140-86-4, name is 6-Isopropoxynicotinonitrile, the common compound, a new synthetic route is introduced below. Formula: C9H10N2O

Example 93 2-[6-Isopropoxy-3-pyridyl]-4H-1,3-benzothiazine-4-one A mixture of methyl thiosalicylate (1.85 g, 11.0 mmol), 2-isopropoxy-5-cyanopyridine (1.62 g, 10.0 mmol), triethylamine (1.80 ml, 12.9 mmol) and toluene (10 ml) was refluxed under nitrogen atmosphere for 30 hrs.. The reaction mixture was concentrated.. The residue was subjected to a silica gel column chromatography, eluted with ethyl acetate-hexane (2:1, v/v) and recrystallized from ethyl acetate-isopropylether to give the titled compound (0.89 g, 30 %). mp. 109.7-110.4 C IR (KBr): 1663, 1595, 1570, 1522, 1487, 1381, 1285, 1238, 1096, 1063, 1030, 947, 922, 837, 745 cm-1.1H-NMR (CDCl3) delta: 1.37 (3H, s), 1.39 (3H, s), 5.38-5.47 (1H, m), 6.78 (1H, d), 7.43 (3H, m), 8.38 (1H, dd, J = 2.5, 8. 8 Hz), 8.52 (1H, d, J = 7.6 Hz), 8.96 (1H, d, J = 2.5 Hz).

The synthetic route of 195140-86-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Takeda Chemical Industries, Ltd.; EP1424336; (2004); 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 887707-23-5, name is 2-Hydroxy-5-iodo-3-(trifluoromethyl)pyridine. This compound has unique chemical properties. The synthetic route is as follows. HPLC of Formula: C6H3F3INO

A mixture of 5-iodo-3-(trifluoromethyl)pyridin-2-ol (53 g, 0.18 mmol) and POCl3 (67 mL, 0.73 mmol) in DMF (50 mL) was heated to 110C for 4h. The reaction mixture was cooled to room temperature and then slowly poured into an ice/water bath. The brown solid was filtered and washed with water. It was then dissolved in DCM, washed with an aqueous saturated solution of sodium thiosulfate (2x), dried over sodium sulfate, and concentrated to dryness to afford 47 g of 2-chloro-5-iodo-3-(trifluoromethyl)pyridine as a pale yellow solid. lK NMR (300 MHz, DMSO-d6) delta 8.79 (d, 1H), 8.29 (d, 1H).

With the rapid development of chemical substances, we look forward to future research findings about 887707-23-5.

Reference:
Patent; ARAGON PHARMACEUTICALS, INC.; SMITH, Nicholas, D.; BONNEFOUS, Celine; JULIEN, Jackaline, D.; WO2011/103202; (2011); A2;,
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. 1206775-52-1, name is 5-Bromo-6-methoxypicolinaldehyde. A new synthetic method of this compound is introduced below., Computed Properties of C7H6BrNO2

To a stirred suspension of 5-bromo-6- methoxypicolinaldehyde (1.9 g, 8.6 mmol) in EtOH/water (22 mL, 10/1) hydroxylamine hydrochloride (1.2 g, 17.2 mmol) and sodium acetate (2.1 g, 25.8 mmol) were added. The mixture was stirred at room temperature for 1 hour, concentrated in vacuo, water (40 mL) was added and it was stirred for 1 hour. The solids were filtered off and washed with water to afford 5-bromo-6-methoxypicolinaldehyde oxime (1.8 g, 92%) as a beige solid. ?H NMR (CDC13, 300 MHz) 8.08 (s, 1H), 7.80 (d, I = 7.9 Hz, 1H), 7.54 (s, 1H), 7.21 (d, I = 7.9 Hz, 1H), 4.03 (s, 3H).

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, 1206775-52-1, 5-Bromo-6-methoxypicolinaldehyde.

Reference:
Patent; FORUM PHARMCEUTICALS INC.; ACHARYA, Raksha; BURNETT, Duane, A.; BURSAVICH, Matthew, Gregory; COOK, Andrew, Simon; HARRISON, Bryce, Alden; MCRINER, Andrew, J.; (451 pag.)WO2016/201168; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 7169-95-1, 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. 7169-95-1, name is 6-Bromo-2-methyl-[1,2,4]triazolo[1,5-a]pyridine. A new synthetic method of this compound is introduced below.

To 6-bromo-2-methyl-[1,2,4]triazolo[1,5-a]pyridine (0.84 g, 4.00 mmol)Anhydrous 1,4-dioxane (20 mL)Pd2(dba)3 (0.36g, 0.40mmol) was added to the suspension.BINAP (0.49g, 0.79mmol),Benzophenone imine (1.45g, 8.02mmol)And t-BuONa (0.77 g, 8.01 mmol).The reaction mixture was degassed and filled with nitrogen several times.Heat again to 105 C and stir overnight.After the reaction was completed, it was concentrated under reduced pressure.The residue was purified with EtOAc EtOAc EtOAc (EtOAc)The title compound was obtained as a brown liquid (0.34 g, yield 27%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,7169-95-1, 6-Bromo-2-methyl-[1,2,4]triazolo[1,5-a]pyridine, and friends who are interested can also refer to it.

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Jiatuo Sciences Corporation; Xi Ning; Li Minxiong; Peng Ju; Li Xiaobo; Zhang Tao; Hu Haiyang; Chen Wuhong; Bai Changlin; Ke Donghua; Chen Peng; (217 pag.)CN109776522; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 942473-59-8, 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.942473-59-8, name is 2,5-Dibromoisonicotinic acid, molecular formula is C6H3Br2NO2, molecular weight is 280.9, as common compound, the synthetic route is as follows.

A 20-L 4-necked round-bottom flask purged and maintained under a N2 atmosphere was charged with 2,5-dibromoisonicotinic acid (1.030 Kg, 3.67 mol, 1.00 equiv), TEA (484 g, 4.78 mol, 1.30 equiv), tert-butanol (10 L) followed by the addition of DPPA (1215 g, 4.41 mol, 1.20 equiv). The resulting solution was stirred overnight at 80 C. This reaction was repeated for 5 times. The resulting mixture was concentrated in vacuo, diluted with 20 L of water and extracted with 3×15 L of EtOAc. The organic layers were combined, washed with 2×15 L of brine, dried (Na2SO4), filtered and concentrated in vacuo. The residue was purified by SiO2 chromatography eluting with an EtOAc/petroleum ether gradient (1:30 to 1:15) to afford 3.2 Kg (41%) of tert-butyl 2,5-dibromopyridine-4-ylcarbamate (A-3) as a white solid

Statistics shows that 942473-59-8 is playing an increasingly important role. we look forward to future research findings about 2,5-Dibromoisonicotinic acid.

Reference:
Patent; Genentech, Inc.; Array BioPharma Inc.; Blake, Jim; Chen, Huifen; Chicarelli, Mark; Gaudino, John; Gazzard, Lewis; Kintz, Sam; Mohr, Pete; Robarge, Kirk; Schwarz, Jacob; Zhou, Aihe; US2014/66453; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 129747-52-0, 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 129747-52-0 as follows.

To a solution of the alcohol (655 mg, 3.92 mmol.) in DCM (7 mL) was added Dess-Martin periodinane (3.3 g, 7.84 mmol.). Stirred for 16h, then diethyl ether was added. The reaction was concentrated, and then partitioned between diethyl ether and a solution of sodium thiosulfate (6.8 g, 43.12 mmol.) in saturated NaHCO3 (50 mL). The aqueous layer was extracted using diethyl ether (2×). The combined organic extracts were dried with MgSO4 and concentrated. The crude product was purified by column chromatography to yield 6 (460 mg, 2.78 mmol, 71%). 1H-NMR (DMSO-d6): delta=10.03 (s, 1H), 8.33 (d, J=8Hz, 1H), 8.25 (dd, J=8 Hz+8 Hz, 1H), 8.15 (d, J=8 Hz, 1H), 3.95 (s, 3H). Calculated mass=165.1, [M]+=165.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,129747-52-0, its application will become more common.

Reference:
Patent; Wyeth; US2006/19965; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem