Month: April 2022

Adding a certain compound to certain chemical reactions, such as: 16328-62-4, 1H-Imidazo[4,5-b]pyridin-2(3H)-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, Quality Control of 1H-Imidazo[4,5-b]pyridin-2(3H)-one, blongs to pyridine-derivatives compound. Quality Control of 1H-Imidazo[4,5-b]pyridin-2(3H)-one

Under argon, 1 ,3-dihydroimidazo[4,5-b]pyridin-2-one (1.500 g, 1 1.10 mmol) was dissolved in DMF (20 ml_). Then sodium hydride (0.4662 g, 1 1 .66 mmol) was added portion-wise over 15 minutes. The resulting suspension was stirred at room temperature for 1 hour. Then di-tert-butyl dicarbonate (2.47 g, 1 1.10 mmol), dissolved into DMF (16.9 ml_), was added dropwise over 10 minutes and the orange solution obtained was stirred at room temperature for 3 hours. Some MeOH was carefully added to quench the reaction mixture and then water was added. The pH of the solution was 8 to 9. The aqueous layer was extracted once with ethyl acetate and this extract was discarded (removal of impurities) then the pH was adjusted to 7 with 4 M aq. HCI solution and extraction was carried out with ethyl acetate. The combined organic layers were washed with water (x2), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure at 40C to afford tert-butyl 2-oxo-3H- im idazo[4 , 5-b] pyrid ine- 1 -carboxylate. NMR (400 MHz, CDCI3): d ppm 8.80-10.50 (br s, 1 H), 8.13 (m, 1 H), 8.00 (dd, J=7.89, 1.28 Hz, 1 H), 7.10 (dd, J=7.89, 5.32 Hz, 1 H), 1.69 (s, 9H). LC-MS: Rt = 0.75 min, MS ES+ = 236 (M+H+).

The synthetic route of 16328-62-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SYNGENTA CROP PROTECTION AG; BIGOT, Aurelien; SCHAETZER, Juergen, Harry; JUNG, Pierre, Joseph, Marcel; STOLLER, Andre; GAGNEPAIN, Julien, Daniel, Henri; HALL, Roger, Graham; RENDINE, Stefano; COMPAGNONE, Nicola; (122 pag.)WO2020/30503; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 2739-74-4, 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. 2739-74-4, name is Ethyl 3-(2-Pyridyl)propanoate, molecular formula is C10H13NO2, 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 5 3-(2-pyridyl)propanoic acid, hydrazide (5) STR16 To a stirring 5 mL EtOH solution of 0.58 g (3.2 mmol) of ethyl 3-(2-pyridinyl)propanoate (4), prepared as described above in Example 4, was added 0.32 g (6.5 mmol) of hydrazine hydrate. The reaction was heated at reflux for three weeks. Although the reaction was still incomplete, the solvent was removed under vacuum. The resulting gum was triturated with diethyl ether (Et2 O). The product remained a gum. The yield of 3-(2-pyridyl)propanoic acid, hydrazide (5) was 0.22 g (42%). This product was used immediately in the manner described in Example 6 below.

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 2739-74-4, Ethyl 3-(2-Pyridyl)propanoate.

Reference:
Patent; G. D. Searle & Co.; US5378840; (1995); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 119396-04-2, 4-Chloro-2-(chloromethyl)pyridine hydrochloride, 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, 119396-04-2, blongs to pyridine-derivatives compound. Computed Properties of C6H6Cl3N

4-chloro-2-(chloromethyl)pyridine hydrochloride (200 mg, 1.02 mmol) was dissolved in chloroform (15 mL) and cooled in water/ice bath m-chloroperoxobenzoic acid (77%, 350mg, 1.56 mmol) was added and the reaction mixture was stirred for 24 hours while letting towarm up to room temperature. The solvent was evaporated on rotary evaporator and theresidue was purified by flash chromatography on silica in 5% methanol / 95 %dichloromethane mixture, giving 143 mg of the product as white solid (0.803 mmol, 79 % yield).500 MHz): 4.90 (C H2, s, 2H); 7.26 ( arom ., dd, 1H,3/HH= 7 Hz,4/HH = 3 Hz); 7.64 (arom., d, 1H,4/HH= 3 Hz); 8.20 (arom., d, 1H,3/HH= 7 Hz);13C{ NMR (CDCl3, 25 C, 125 MHz): 5c 39.6 (CH2, s); 125.6 (arom., s); 125.9 (arom., s); 132.4 (arom., s); 140.2 (arom., s); 148.7 (arom., s).HRMS (ESI) m/z: [(M + H)+] (C6H6Cl2NO) calculated: 177.9821, found: 177.9820.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,119396-04-2, its application will become more common.

Reference:
Patent; USTAV ORGANICKE CHEMIE A BIOCHEMIE AV CR, V.V.I.; POLASEK, Miloslav; (102 pag.)WO2019/106182; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 777931-67-6 , The common heterocyclic compound, 777931-67-6, name is 3-Bromo-2-chloro-6-methoxypyridine, molecular formula is C6H5BrClNO, 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 stirred solution of 31(6.83 g, 30.7 mmol) in THF (120 mL) was added i-PrMgCl·LiCl (ca.1.0 Msolution in THF, 32.2 mL, 32.2 mmol) at -20C. After 2 h, DMF (7.2 mL, 92.1 mmol) was added dropwise at -20C. The resulting mixture was stirred at room temperature for 30 min. The reaction mixture was quenched with saturated aqueous NH4Cl and extracted with EtOAc. The organic layer was dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The crude material including 12was applied to the following reaction without further purification.

The synthetic route of 777931-67-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Inai, Makoto; Ouchi, Hitoshi; Asahina, Aya; Asakawa, Tomohiro; Hamashima, Yoshitaka; Kan, Toshiyuki; Chemical and Pharmaceutical Bulletin; vol. 64; 7; (2016); p. 723 – 732;,
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

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

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

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

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

Electric Literature of 866807-27-4, Adding some certain compound to certain chemical reactions, such as: 866807-27-4, name is 3-Amino-6-chloropyridine-2-carboxylic acid,molecular formula is C6H5ClN2O2, 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 866807-27-4.

Step 4: Preperation of 3-amino-6-chloro-pyridine-2- carboxylic acid methyl ester; 3-Amino-6-chloro-pyridine-2-carboxylic acid (636 mg) was suspended in methanol (8 mL) and toluene (22 mL) was added. A solution of (trimethylsilyl) diazomethane (2.0 M in hexane,2.4 mL) was added slowly to the reaction mixture. After 1 hour stirring at room temperature, another portion of(trimethylsilyl) diazomethane (550 mul) was added and the mixture was stirred for additional 45 minutes. The reaction mixture was quenched with water and extracted 3x with ethyl acetate. The combined organic layer was washed with 2N hydrochloric acid, saturated bicarbonate solution and brine, dried over MgSO4 and concentrated in vacuum. The residue was purified by column chromatography (silica gel 60, choroform/ethyl acetate = 50:1, Rf = 0.30) to afford 365 mg of the title compound of the formulaas a yellow solid. The compound still contained -30% of an unknown impurity and was used in the next step without further purification.1H-NMR (CDCl3, TMS) delta (ppm) : 3.96 (3H, s) , 5.82 (2H, br s), 7.05 (IH, d, J = 9 Hz), 7.23 (IH, d, J = 9 Hz).

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. 866807-27-4, 3-Amino-6-chloropyridine-2-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SUMITOMO CHEMICAL COMPANY, LIMITED; WO2008/130021; (2008); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem