Tag: M.W:100-200

Electric Literature of 7205-46-1 ,Some common heterocyclic compound, 7205-46-1, molecular formula is C7H6ClN3, 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.

4-Amino-3-ethyl-phenol (100 mg, 0.73 mmol, 1.0 equiv), 6-Chloro-l -methyl- 1H- imidazo[4,5-c]-pyridine (134 mg, 0.80 mmol, 1.1 equiv), Cs2C03 (714 mg, 2.19 mmol, 3.0 equiv), BetaGammaNuAlphaRho (46 mg, 0.07 mmol, 0.1 equiv), and Pd2(dba)3 (33 mg, 0.04 mmol, 0.05 equiv) were dissolved in dry dioxane (5 mL) under N2 atmosphere. The mixture was sonicated for 5 mn under N2 flow and then re fluxed for 20h. Full conversion was observed by LCMS. It was then cooled down and concentrated to dryness, diluted in DCM and washed with water (3x 20 mL). The aqueous layer was extracted with DCM (3x 30 mL) and the combined organic layer was dried over Na2SO i, filtered and concentrated to dryness. Purification was performed by column chromatography using the following eluant: EtOAc/Petroleum Ether (1 : 1) to EtOAc (over 5 CV), MeOH/EtOAc (1 : 19) (10 CV), MeOH/EtOAc (1 :9) (10 CV) to afford the desired compound

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,7205-46-1, its application will become more common.

Reference:
Patent; GALAPAGOS NV; MENET, Christel Jeanne Marie; SCHMITT, Benoit Antoine; GENEY, Raphael Jean Joel; DOYLE, Kevin James; PEACH, Joanne; PALMER, Nicholas John; JONES, Graham Peter; HARDY, David; DUFFY, James Edward Stewart; WO2013/117645; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 76041-71-9, 3-Chloro-2-hydroxy-5-(trifluoromethyl)pyridine, 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, Recommanded Product: 76041-71-9, blongs to pyridine-derivatives compound. Recommanded Product: 76041-71-9

Preparation of N-({[3-chloro-5-(trifluoromethyl)pyridin-2-ylloxy}methyl)-2- (trifluoromethyl)benzamide (compound 1)To a solution of 0.20Og (1.01 mmol) of 3-chloro-5-(trifluoromethyl)pyridin- 2-ol in 5 ml of a mixture tetrahydofurane/NaOH IM (4/1) was added 0.263g {[2- (trifluoromethyl)benzoyl]amino}methyl acetate (1.01 mmol). The mixture was stirred 14 hours at room temperature.The reaction mixture was poured into 10ml of diethyl ether. Afire separation of the phases, the organic phase was washed twice with 5ml of water and dried over magnesium sulphate.After filtration, the solvent was evaporated and the residue was purified by flash chromatography on silica gel (eluent: heptane/ethyl acetate: 6/4) to give N-({[3- chloro-5-(trifluoromethyl)pyridin-2-yl]oxy}methyl)-2-(trifluoromethyl)benzamide: 298 mg (74%). Mass spectrum : 399 (M+ 1).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,76041-71-9, 3-Chloro-2-hydroxy-5-(trifluoromethyl)pyridine, and friends who are interested can also refer to it.

Reference:
Patent; BAYER CROPSCIENCE SA; WO2008/3744; (2008); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 101083-92-5 ,Some common heterocyclic compound, 101083-92-5, molecular formula is C7H5N3O2, 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 43; [0221] This example illustrates a preparation of 6-methoxy-2-(l-methyl-lH-pyrrolo[2,3- delta]pyridin-5-yl)isoindolin-l-one in an embodiment of the invention.; Step A: Synthesis of l-methyl-5-nitro-7-azaindole,; [0222] A solution of 5-nitro-7-azaindole (0.195 g, 1.2 mmol) in DMF (10 mL) was treated with NaH (60%, 0.057 g, 1.44 mmol), followed by iodomethane (0.204 g, 1.44 mmol). The reaction mixture was stirred at room temperature for 4.5 h, then poured into water (200 mL) and extracted with dichloromethane (3 chi100 mL). The combined organic layer was washed with brine (100 mL), dried over sodium sulfate, and concentrated. The crude product was purified by chromatography (silica, 50:50 ethyl acetate/hexanes) to yield l-methyl-5-nitro-7-azaindole (0.152 g, 72%) as a yellow solid: 1H NMR (500 MHz, CDCl3) delta 9.23 (d, J= 2.4 Hz, IH), 8.76 (d, J= 2.4 Hz, IH), 7.36 (d, J= 3.6 Hz, IH), 6.66 (d, J= 3.5 Hz, IH), 3.96 (s, 3H).

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. 101083-92-5, 5-Nitro-1H-pyrrolo[2,3-b]pyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; The United States of America, as represented by the Secretary, Department of Health and Human Services; Science Applications International Corporation (SAIC); Albany Molecular Research, Inc.; WO2009/42907; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1513-65-1, 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 1513-65-1 as follows.

Example 13: (4S)-Lambda/-Methyl-Lambda/-(f5-(4-methyl-1-piperazinvnimidazo? .2-aloyridin-2- v?methyl)-3,4-dihvdro-2H-pyranof3,2-b1pyridin-4-arnine EPO A) 6-Fluoro-2-pyridinamine: A solution of 2,6-difluoropyridine (50 g, 434 mmol) in ammonium hydroxide (200 mL, 28.0- 30.0%) was heated at 1050C in a steel bomb for 15 hours. The reaction was cooled in an ice bath and the precipitate filtered, rinsed with cold water, and dried to yield 6-fluoro-2- pyridinamine (45.8 g, 94% yield) as a white solid. 1H-NMR (CDCI3): delta 7.53 (m, 1 H)1 6.36 (dd, 1 H), 6.26 (dd, 1 H), 4.56 (s, 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1513-65-1, its application will become more common.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2006/76131; (2006); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 54903-50-3, 4,5,6,7-Tetrahydrothieno[3,2-c]pyridine, 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, 54903-50-3, blongs to pyridine-derivatives compound. Application In Synthesis of 4,5,6,7-Tetrahydrothieno[3,2-c]pyridine

EXAMPLE 7 (+-)-(2-chlorophenyl)-(6,7-dihydro-4H-thieno[3,2-c]pyrid-5-yl)acetonitrile (IV) To 19.5 g (250 mmol) KCN dissolved in water (20 mL) and 43 g (250 mmol) 6,7-dihydro-4H-thieno[3,2-c]pyridine was added, followed by dropwise addition of 50 ml concentrated hydrochloric acid. After the addition was complete, a solution of 33 g (230 mmol) o-chlorobenzaldehyde in 100 mL methanol was added dropwise and stirred for 8 hrs at 31 C. The pH of the reaction mixture was adjusted to 7.5-8.0 using NH4OH and the product was extracted with ethyl acetate (2*500 mL) and washed with water (2*500 mL), brine (500 mL) and was dried over sodium sulfate. The solvent was evaporated under reduced pressure to give of 50 g (74%) the product with melting point of about 123-125 C. The product obtained was characterized using IR spectrum, Mass, 13C -NMR and 1H-NMR and was found to be identical to the product obtained in example 1.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,54903-50-3, its application will become more common.

Reference:
Patent; CADILA HEALTHCARE LIMITED; US2002/177712; (2002); 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.6000-50-6, name is 2,3-Dihydro-1H-pyrrolo[3,4-c]pyridine dihydrochloride, molecular formula is C7H10Cl2N2, molecular weight is 193.0737, as common compound, the synthetic route is as follows.Recommanded Product: 6000-50-6

To a solution of Intermediate 103 (4.07 g, 10.5 minol) in THE (45 mL) was added at r.t. 4- nitrophenylchloroformate (2.11 g, 10.5 minol). After heating to 6000 for 3 h the reaction mixture was concentrated under reduced pressure and the residue taken up in dichloromethane(40 mL). To the solution was added at r.t. N,N-diisopropylamine (4.28 mL, 24.6 minol) and 2,3- dihydro-IH-pyrrolo[3,4-c]pyridine dihydrochloride (1.53 g, 7.93 minol). After stirring for 20 h at this temperature further N,N-diisopropylamine (1 .50 mL) and THE (25 mL) was added. After 30 min stirring at r.t. the reaction mixture was heated to 60°C. After cooling to r.t. the reaction mixture was poured on water and aq. I N NaOH was added. After separation of the organicphase the aqueous phase was extracted 2 x with dichloromethane and the combined organic extracts were washed with brine and filtered through a phase separator filter. After removal of the solvent the crude product was purified by comumn chromatography (silica gel, ethyl acetate/ethanol gradient) to give the title compound (1.72 g, 75percent purity, 2.54 minol, 32percent).LC-MS (Method 6): Rt = 1.27 min; MS (ESIpos): m/z = 508 [M÷H].

At the same time, in my other blogs, there are other synthetic methods of this type of compound,6000-50-6, 2,3-Dihydro-1H-pyrrolo[3,4-c]pyridine dihydrochloride, and friends who are interested can also refer to it.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; GIESE, Anja; QUANZ-SCHOEFFEL, Maria; MUeLLER, Thomas; GUeNTHER, Judith; BOeHNKE, Niels; GRIEBENOW, Nils; BARAK, Naomi; BOeMER, Ulf; NEUHAUS, Roland; OSMERS, Maren; KOPITZ, Charlotte Christine; KAULFUSS, Stefan; REHWINKEL, Hartmut; WEISKE, Joerg; BADER, Benjamin; CHRISTIAN, Sven; HILLIG, Roman; (426 pag.)WO2018/86703; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 114-33-0, 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 114-33-0, name is N-Methylnicotinamide. This compound has unique chemical properties. The synthetic route is as follows.

General procedure: Complex 1 was prepared by the reaction of an aqueous solution of copper(II) acetate monohydrate (1mmol, 0.20g) with N-methylnicotinamide (2mmol, 0.27g) followed by addition of 4-fluorobenzoic acid (2mmol, 0.28g). The reaction mixture was stirred until a blue product was precipitated (3days). The fine blue microcrystals were filtered off, washed with a small portion of water and dried at ambient temperature. The mother liquor obtained from filtration were left to crystallize. The blue crystals suitable for X-ray structure determination were separated after several days. Yield: 0.41g (65%).

According to the analysis of related databases, 114-33-0, the application of this compound in the production field has become more and more popular.

Reference:
Article; Hala?ka, Jozef; Lokaj, Jan; Jomova, Klaudia; R??i?kova, Zde?ka; Mazur, Milan; Moncol, Jan; Polyhedron; vol. 175; (2020);,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 866319-00-8, 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 866319-00-8, name is 5-Fluoro-1H-pyrrolo[2,3-b]pyridine. This compound has unique chemical properties. The synthetic route is as follows.

b) 5-fluoro-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde can be prepared as in Example 2 but from 545 mg of 5-fluoro-1H-pyrrolo[2,3-b]pyridine, in a mixture of 3.4 cm3 of water and 1.6 cm3 of acid acetic, and 545 mg of 1,3,5,7-tetraazatricyclo[3.3.1.1~3,7~]-decane. 265 mg of 5-fluoro-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde is obtained in the form of a beige solid with the following physical characteristics: 1H-NMR spectrum at 400 MHz: 8.15 (dd, J=3 and 9 Hz, 1H); 8.36 (dd, 1.8 and 3 Hz, 1H); 8.53 (s, 1H); 9.90 (s, 1H); 12.79 (s broad, 1H).

According to the analysis of related databases, 866319-00-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; sanofi-aventis; US2009/253679; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 55314-16-4, 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 55314-16-4 as follows.

Experimental Preparation of intermediates; Synthesis of 6-methyl-Nl-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-l,3-diamine 5; To 2-amino-4-nitro toluene 1 (0.033 mol) in n-butanol (29 mL) is added nitric acid (2.1 g, 65% in water) followed by cyanamide solution in water (2 mL, 0.047 mmol). The resulting mixture is heated at reflux for 25 h. After cooling to 0 0C, filtration and washing with 1 : 1 = ethanol : diethyl ether (30 mL), 2-methyl-5-nitrophenyl guanidine nitrate 2 is obtained. To 2-methyl-5-nitrophenyl guanidine 2 (0.0074 mol) in isopropanol (15 mL) is added 3 (0.0074 mol) and sodium hydroxide flakes (0.008 mol). The resulting mixture is heated at reflux for 12 h. After cooling to 0 0C, the product is collected by filtration and washed with isopropanol (6 mL) and methanol (3 mL) to afford 4. 1H NMR (400MHz, Cl6-DMSO) delta 9.31 (s, IH), 9.24 (s, IH), 8.78 (m, IH), 8.70 (m, IH), 8.61 (m, IH), 8.47 (m, IH), 7.88 (m, IH), 7.55 (m, 3H), 2.39 (s, 3H). MS (m/z) (M+l)+: 278.2

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,55314-16-4, its application will become more common.

Reference:
Patent; IRM LLC; NOVARTIS AG; LI, Xiaolin; LIU, Xiaodong; MOLTENI, Valentina; CHIANELLI, Donatella; LOREN, Jon; NABAKKA, Juliet; WO2008/137794; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 17282-00-7, 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.17282-00-7, name is 3-Bromo-5-methylpyridin-2-amine, molecular formula is C6H7BrN2, molecular weight is 187.04, as common compound, the synthetic route is as follows.

General procedure: Under N2 atmosphere, to a solution of palladium acetate (120 mg, 0.53 mmol, 5 mol %) and XANTPHOS (309 mg, 0.53 mmol, 5 mol %) in anisole (30 mL) was added 3-bromo-5-methyl-pyridin-2-ylamine (5) (2.0 g, 10.7 mmol, 1.0 equiv), aryl iodides (6) (10.7 mmol) and cesium carbonate (4.9 g, 15.0 mmol, 1.4 equiv), and the mixture was stirred at 130 C for 1-13 h. After cooling to room temperature, water (40 mL) was added to the mixture. The mixture was concentrated in vacuo and ethyl acetate (100 mL) was added to the residue. The organic layer was washed with water (20 mL) and concentrated in vacuo to give the crude product, which was purified by flash chromatography to give 7.

Statistics shows that 17282-00-7 is playing an increasingly important role. we look forward to future research findings about 3-Bromo-5-methylpyridin-2-amine.

Reference:
Article; Mineno, Masahiro; Sera, Misayo; Ueda, Tsuyoshi; Mizuno, Masahiro; Yamano, Mitsuhisa; Mizufune, Hideya; Zanka, Atsuhiko; Tetrahedron; vol. 70; 35; (2014); p. 5550 – 5557;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem