Day: September 17, 2021

Adding a certain compound to certain chemical reactions, such as: 14150-94-8, 1-Methyl-3,5-dinitro-1H-pyridin-2-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, HPLC of Formula: C6H5N3O5, blongs to pyridine-derivatives compound. HPLC of Formula: C6H5N3O5

11.2 (3-Nitro-5,6,7,8-tetrahydro-quinolin-5 and 7-yl)-carbamic acid benzyl ester; A mixture of 1-methyl-3,5-dinitro-2-pyridone (3.66 g, 18.38 mmol) and (3-oxo- cyclohexyl)-carbamic acid benzyl ester (4.55 g, 18.39 mmol) in methanolic am¬ monia (1 M1 140 ml) was heated at 65C for 1.5 h. It was then concentrated and digested in CH2CI2. The organic layer was washed with H2O (x2), dried (Na2SO4) and evaporated. The residue was chromatographed on silica gel (heptane:ethyl acetate, 3:1) to afford a mixture 1/2 of the 5 and 7 regioisomers (4.51 g, 75% for two steps) as a pale yellow gum. MS (ESI+) m/z = 328.1 [M+H]+ 1H NMR (400 MHz, CDCI3) : delta (ppm) 1.83 (m, 1.5H), 2.01 (m, 1H), 2.20 (m, 1.5H), 2.90 (dd, J = 18.1 , 8.7 Hz1 1H), 3.00 (t, J = 6.4 Hz1 2H), 3.05 (t, J = 6.4 Hz, 1 H)13.43 (dd, J = 18.1 , 5.2 Hz1 1H)1 4.16 (m, 1H)1 4.81 (bs, 1 H)1 5.03 (bs, 1H), 5.12 (s, 2H), 5.19 (s, 1 H), 7.36 (m, 7.5 H)1 8.19 (bs, 1H), 8.46 (bs, 0.5H)1 9.20 (d, J = 1.9 Hz, 1 H), 9.23 (d, J = 2.1 Hz1 0.5H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,14150-94-8, 1-Methyl-3,5-dinitro-1H-pyridin-2-one, and friends who are interested can also refer to it.

Reference:
Patent; ABBOTT GMBH & CO.KG; WO2006/40178; (2006); 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. 1334411-79-8, name is 4-Bromo-2-(2,6-dichlorophenyl)-1H-imidazo[4,5-c]pyridine. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 1334411-79-8

To a microwave tube was added 4-bromo-2-(2, 6-dichlorophenyl)-lH-imidazo-[4,5- c]-pyridine (0.050 g, 0.15 mmol), tert-butyl-4-amino-lH-pyrazole-l-carboxylate (0.032 g, 0.17 mmol), Pd2(dba)3 (0.013 g, 0.015 mmol), XantPhos (0.017 g, 0.03 mmol), Cs2C03 (0.098 g, 0.03 mmol) and dioxane (1.2 niL). The mixture was degassed with N2 for 1 min. The resulting mixture was irradiated in a microwave reactor at 160 C for 2 housr and then cooled to room temperature. The mixture was filtered with Celite and the filtrate was concentrated by vacuum. The residue was purified by prep-HPLC (Gilson GX 281 , Shim- pack PRC-ODS 250 mm x 20 mm x 2, gradient: CH3CN / 10 mm/L NH4HC03, 17 min) to give the desired product (15 mg, 15% yield). ¾ NMR(MeOD- 4, 500 MHz): delta 8.09 (s, 1H), 7.90 (d, J = 5.5 Hz, 1H), 7.76 (s, 1H), 7.59 (m, 3H), 6.97 (d, J = 5.5 Hz, 1H). LCMS(ESI) m/z: 345.2 [M+H+].

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, 1334411-79-8, 4-Bromo-2-(2,6-dichlorophenyl)-1H-imidazo[4,5-c]pyridine.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; LAI, Yingjie; LIANG, Jun; MAGNUSON, Steven R.; TSUI, Vickie H.; ZHANG, Birong; ROBARGE, Kirk; WO2011/113802; (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. 1570-48-5, name is 1-(Pyridin-3-yl)propan-1-one. A new synthetic method of this compound is introduced below., Safety of 1-(Pyridin-3-yl)propan-1-one

A solution of the 3-propionylpyridine (5g, 37 mmol) , (S)-(-)-2-methylpropane-2- sulfinamide (4.7 g, 38.8 mmol) and titanium (IV) ethoxide (17.8g, 78 mmol) in THF (100 mL) was heated at 80C for 3 days. After cooling, brine (100 mL) and EA (100 mL) were added. The mixture was stirred at RT for 1 h. The mxture was filtered through Celite, and the pad was washed with EA. The organic phase was seperated, concentrated, and the residue was chromatographed (eluted with 2:1 hexane:EA) to give the product as a colorless oil (8.15g, 92%).

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, 1570-48-5, 1-(Pyridin-3-yl)propan-1-one.

Reference:
Patent; EXITHERA PHARMACEUTICALS, INC.; CHENARD, Bertrand, L.; XU, Yuelian; STASSEN, Frans, L.; HAYWARD, Neil, J.; (225 pag.)WO2018/118705; (2018); 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.802325-29-7, name is (5-Fluoropyridin-2-yl)methanol, molecular formula is C6H6FNO, molecular weight is 127.12, as common compound, the synthetic route is as follows.Quality Control of (5-Fluoropyridin-2-yl)methanol

To a stirred solution of (5-fluoropyridin-2-yl)methanol (500 mg, 3.937 mmol, commercial source: Combi-Blocks) and triethylamine (398 mg, 3.937 mmol) in /V,/V-dimethylformamide (10 ml_), mesyl chloride (451 mg, 3.937 mmol) was added at 27 C. The reaction mixture was stirred at 27 C for 2 h. Followed by the addition of sodium azide (384 mg, 5.905 mmol) at 27 C and the reaction mixture was stirred for 12 h at the same temperature. Upon completion, the reaction mixture was concentrated under reduced pressure. The crude compound was purified by column chromatography (silica gel 100-200 mesh) using 5% ethyl acetate in pet ether. The pure fractions were collected and concentrated under reduced pressure to afford 2-(azidomethyl)-5- fluoropyridine (150 mg, 25%) as a brown liquid. NMR (400 MHz, CDCI3) 5 8.46 (d, J = 2.6 Hz, 1 H), 7.47-7.40 (m, 1 H), 7.39-7.33 (m, 1 H), 4.48 (s, 2H). MS m/z [M+H]+= 153.12.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,802325-29-7, (5-Fluoropyridin-2-yl)methanol, and friends who are interested can also refer to it.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; ALEMPARTE-GALLARDO, Carlos; ENCINAS, Lourdes; ESQUIVIAS PROVENCIO, Jorge; (206 pag.)WO2019/34729; (2019); 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. 66358-23-4, name is Imidazo[1,2-a]pyridin-5-amine. A new synthetic method of this compound is introduced below., Application In Synthesis of Imidazo[1,2-a]pyridin-5-amine

Example 69: 4-[3-(4-Chloro-phenoxy)-benzyl1-piperazine-1 -carboxylic acid imidazo[1 ,2-aipyridin-5-ylamide.; To a solution of imidazo[1 ,2-a]pyridin-5-ylamine (56.0 mg, 0.421 mmol) in CH2CI2 (2.0 ml_) were added N,N’-disuccinimidyl carbonate (108 mg, 0.421 mmol) and DMAP (51.0 mg, 0.417 mmol). The reaction mixture was stirred at rt for 6 h, then treated with 1-[3-(4-chloro-phenoxy)-benzyl]-piperazine hydrochloride (158 mg, 0.420 mmol) and diisopropylethylamine (109 mg, 0.840 mmol) and stirred for an additional 16 h at rt. The reaction mixture was diluted with EtOAc and extracted with H2O then saturated aqueous NaCI. The organic layer was dried (MgSO4), and concentrated. The crude residue was purified (FCC, 2 N NH3 in MeOH/DCM) to give 4-[3-(4-chloro- phenoxy)-benzyl]-piperazine-1 -carboxylic acid imidazo[1 ,2-a]pyridin-5-ylamide (90.0 mg, 46%). MS (ESI+): calcd for C25H24CIN5O2 m/z 461.17, found 462.2 (M+H)+. 1H NMR (d6-DMSO): 9.21 (br s, 1 H), 7.57 (s, 1 H), 7.54 (d, J = 1.2, 1 H), 7.47-7.35 (m, 4H), 7.23 (dd, J = 9.0, 7.2, 1 H), 7.15 (d, J = 7.6, 1 H), 7.06-7.01 (m, 3H), 6.94 (dd, J = 8.1 , 1.9, 1 H), 6.73 (d, J = 7.1 , 1 H), 3.54 (s, 2H), 3.52-3.45 (m, 4H), 2.46-2.40 (m, 4H).

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, 66358-23-4, Imidazo[1,2-a]pyridin-5-amine.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; BREITENBUCHER, J., Guy; KEITH, John, M.; TICHENOR, Mark, S.; CHAMBERS, Alison, L.; JONES, William, M.; HAWRYLUK, Natalie, A.; TIMMONS, Amy, K.; MERIT, Jeffrey, E.; SEIERSTAD, Mark, J.; WO2010/68453; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 72990-37-5, 3-Chloroisonicotinaldehyde, 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, Safety of 3-Chloroisonicotinaldehyde, blongs to pyridine-derivatives compound. Safety of 3-Chloroisonicotinaldehyde

Magnesium (86.5 mg, 3.60 mmol) was stirred vigorously under nitrogen for 30 min. THF (2 mL) and dibromoethane (2 drops) were added and the reaction mixture was warmed to 50 C. A solution of 4-bromotetrahydropyran (495 mg, 3.00 mmol) in THF (4 mL) was added drop-wise over 5 min and the reaction mixture was heated at reflux for 2 h. A solution of 3-chloro-4-pyridaldehyde (170 mg, 1.20 mmol) in THF (4 mL) was added drop-wise over 5 min and the reaction mixture was heated at reflux for 6 h, stirred at room temperature overnight and heated at reflux for 8 h. The reaction mixture was cooled to 0 C and quenched with sat aq NH4C1 (10 mL). The reaction mixture was diluted with EtOAc (40 mL) and the aqueous fraction was extracted with EtOAc (3 x 40 mL). The combined organic fractions were washed with sat aq Na2C03 (20 mL), dried (MgS04) and concentrated in vacuo. The residue was purified by normal phase column chromatography to give the crude title compound as a pale yellow gum (69.0 mg, 25%). LCMS (ES+): 228.2 (M+H)+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,72990-37-5, 3-Chloroisonicotinaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; Proximagen Limited; EVANS, David; CARLEY, Allison; STEWART, Alison; HIGGINBOTTOM, Michael; SAVORY, Edward; SIMPSON, Iain; NILSSON, Marianne; HARALDSSON, Martin; NORDLING, Erik; KOOLMEISTER, Tobias; WO2011/113798; (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. 113293-71-3, name is (6-Aminopyridin-3-yl)methanol. A new synthetic method of this compound is introduced below., Quality Control of (6-Aminopyridin-3-yl)methanol

General procedure: Triphenylphosphine (TPP) (280 mg, 1.07 mmol) was added in portions to a freshly prepared solution of the designated alcohol (1.0 mmol) and the specified phenolic acid (1.0 mmol equivalent) in anhydrous THF (3.5 mL) at 0 C. Diisopropylazodicarboxylate (DIAD) (208 mL, 1.0 mmol) was then added dropwise to the mixture. The reaction mixture was stirred at 0 C for 30 min. The mixture was then warmed and stirring was continued for 48 h at rt [19]. Reactions were monitored till completion by TLC. The reaction mixture was then worked up by removal of the solvent under reduced pressure, saturated solution of NaHCO3 (10 mL) was added, and then the mixture was extracted with EtOAc (3 x 20 mL). The combined organic layers were washed with brine, dried over anhydrous Na2SO4, filtered, and the filtrate was evaporated under reduced pressure to dryness. The crude product was collected and purified by column chromatography(CC) on Sephadex LH-20 using isocratic CH2Cl2 followed by chromatography on Si gel 60 using n-hexane-EtOAc system, gradient elution, to afford 5-9 and 13-47 (Supplementary Information).

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, 113293-71-3, (6-Aminopyridin-3-yl)methanol.

Reference:
Article; Mohyeldin, Mohamed M.; Busnena, Belnaser A.; Akl, Mohamed R.; Dragoi, Ana Maria; Cardelli, James A.; El Sayed, Khalid A.; European Journal of Medicinal Chemistry; vol. 118; (2016); p. 299 – 315;,
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. 178876-82-9, name is Methyl 6-amino-5-bromopicolinate. A new synthetic method of this compound is introduced below., name: Methyl 6-amino-5-bromopicolinate

A solution of ethyl 2-mercaptoacetate (1.473 mL) in DMF (48 mL) was ice-cooledand treated with sodium hydride (540 mg of a 60% dispersion in oil). After 1 h methyl 6-amino-5-bromopyridine-2-carboxylate (3 g) (T.R. Kelly and F. Lang, J. Org. Chem. 61,1996, 4623-4633) was added and the mixture stirred for 16h at room temperature. Thesolution was diluted with EtOAc (1 L), washed with water (3 x 300 mL), dried and evaporated to aoout 10 ml_. The white solid was filtered off and washed with a little EtOActo give the ester (0.95g); LC/MS (APCI~) m/z223 ([M-H]-, 100%).

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, 178876-82-9, Methyl 6-amino-5-bromopicolinate.

Reference:
Patent; GLAXO GROUP LIMITED; WO2006/12396; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 71255-09-9, Adding some certain compound to certain chemical reactions, such as: 71255-09-9, name is 2-Methoxynicotinaldehyde,molecular formula is C7H7NO2, 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 71255-09-9.

[0706] A mixture of trans-3-(4-amino-phenyl)-1-[4-(4-methylpiperazino)cyclohexyl]-1H-pyrazolo[3,4-d]pyrimidin-4-amine (1 eq.), 2-methoxy-3-formyl-pyridine (1.05 eq.), sodium triacetoxyborohydride (3.4 eq.) and acetic acid (3.4 eq) was stirred in anhydrous 1,2-dichloroethane for 16 hours. The reaction mixture was concentrated under reduced pressure, quenched with saturated solution of sodium bicarbonate in water and concentrated again. The residue was purified by preparative HPLC (Hypersil C18, 8 mum, 25 cm; 10-60% acetonitrile-0.1M ammonium acetate over 25 min, 21 mL/min) to yield the desired products. The following two compounds were prepared according to the procedure above: trans-3-(4-[(2-methoxy-3-pyridyl)methyl]aminophenyl)-1-[4-(4-methyl-piperazino)cyclohexyl]-1H-pyrazolo [3,4-d]pyrimidin-4-amine Diacetate [0707] 1H NMR (DMSO-d6, 400 MHz) delta 8.18 (s, 1H), 8.06 (dd, 1H), 7.61 (d, 1H), 7.35 (d, 2H), 6.95 (dd, 1H), 6.69 (d, 2H), 6.51 (t, 1H), 4.60 (m, 1H), 4.26 (d, 2H), 3.94 (s, 3H), 2.64 (s, 3H), 2.6-2.2 (br, 9H), 2.13 (s, 3H), 2.05 (m, 6H), 1.91 (s, 6H), 1.46 (m, 2H); [0708] RP-HPLC (Delta Pak C18, 5 mum, 300A, 15 cm; 5%-85% acetonitrile-0.1M ammonium acetate over 20 min, 1 mL/min) Rt 12.07 min. [0709] MS: MH+ 528.

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. 71255-09-9, 2-Methoxynicotinaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Hirst, Gavin C.; Rafferty, Paul; Ritter, Kurt; Calderwood, David; Wishart, Neil; Arnold, Lee D.; Friedman, Michael M.; US2004/6083; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 109-04-6 , The common heterocyclic compound, 109-04-6, name is 2-Bromopyridine, molecular formula is C5H4BrN, 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.

General procedure: To a solution of n-BuLi (15.00 mmol) in diethyl ether (30.0 mL) at78 C was added dropwise to a solution of bromopyridine(15.00 mmol) in diethyl ether (25.0 mL). The resulting solutionwasstirred at 78 C for 2 h. And then, the solution of Bu3SnCl orMe3SnCl (15.00 mmol) in THF (10.0 mL) was added dropwise andstirred at 78 C for another 3 h. The resulting deep-red solutionwas warmed to room temperature over night and a heavy precipitateformed. Hydrolysis was achieved with a saturated aqueoussolution of NH4Cl. Subsequent treatments (Et2O extraction, dryingon anhydrous Na2SO4, concentration and flash chromatography)afforded pure product.

The synthetic route of 109-04-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ma, Gaizhi; Leng, Yuting; Wu, Yusheng; Wu, Yangjie; Tetrahedron; vol. 69; 2; (2013); p. 902 – 909;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem