Day: April 21, 2022

Electric Literature of 700811-29-6 ,Some common heterocyclic compound, 700811-29-6, molecular formula is C5H6ClN3, 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.

A solution of 4-amino-2-chloropyridine (1.0 g, 7.78 mmol) in 20% sulfuric acid (20 mL) was cooled to 0 C and treated with a solution of sodium nitrite (564 mg, 8.17 mmol) in water (3 mL) at a rate such that the reaction temperature did not exceed 10 C. After 15 minutes, the solution was added to a 0C suspension of tin (li) chloride in 20% sulfuric acid (20 mL). The frothy suspension was stirred for 15 minutes at 0 C and then warmed to room temperature over 15 minutes. The mixture was poured into 100 mL of ice water and made basic with concentrated ammonium hydroxide. The product was extracted with diethyl ether and ethyl acetate repeatedly. The organic layers were dried (sodium sulfate) and concentrated to give crude 2-chloro-4-hydrazinopyridine as a yellow solid (830 mg, 5.78 mmol). The solid was dissolved in tetrahydrofuran (5 mL) and diluted with diethyl ether (15 mL). The solution was treated with 1 N HCI in diethyl ether (5.8 mL, 5.8 mmol). The white precipitate was filtered and washed with ether to give 2-chloro-4-hydrazinopyridine hydrochloride as a white solid (995 mg, 5.53 mmol, 71 % yield). LC-MS (ES+) MH+ = 144.’H NMR (300 MHz, DMSO-d6) b 10.0-9. 40 (br s, 4H), 8.07 (d, J = 6. 1, 1 H), 6.95 (d, J = 1.9, 1 H), 6.86 (dd, J = 5.8, 2.0, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,700811-29-6, its application will become more common.

Reference:
Patent; PHARMACIA CORPORATION; WO2004/58176; (2004); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 75711-01-2, 6-Chloro-5-methoxypyridin-3-amine, 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, 75711-01-2, blongs to pyridine-derivatives compound. Safety of 6-Chloro-5-methoxypyridin-3-amine

To an ice-cooled suspension of 6-chloro-5-(methyloxy)-3-pyridinamine D46 (2.14 g, 13.50 mmol) in HCl 4 M in water (10.12 ml, 40.50 mmol), a solution of sodium nitrite (1.02 g, 14.84 mmol) in water (7 ml) was added dropwise over a 5 min period and the resulting mixture was vigorously stirred at 5 C. for 30 min. To the mixture at 5 C. was added a solution of NaBF4 (2.67 g, 24.29 mmol) in water (17 ml). The thick suspension was collected by filtration, washed with cold water and a little amount of cold EtOH and dried under reduced pressure at 55 C. for 8 h. The resulting black solid was taken-up in xylenes (25 ml) and allowed to reflux for 1 h. The solvent was evaporated under reduced pressure, the residue dissolved in EtOAc and washed with a saturated NaHCO3 aqueous solution. The organic phase was separated, dried (Na2SO4), filtered and the solvent removed under vacuum. The resulting black oil was purified by flash chromatography on silica gel (Biotage SP4 25M, Cy/EtOAc 95/5) to afford the title compound D47 (0.11 g, 0.69 mmol, 5% yield) as a pale yellow solid. 1H NMR (400 MHz, DMSO-d6) delta (ppm): 8.03 (d, 1H), 7.70 (dd, 1H), 3.92 (s, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,75711-01-2, its application will become more common.

Reference:
Patent; ALVARO, GIUSEPPE; AMANTINI, DAVID; BELVEDERE, SANDRO; US2009/22670; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 98027-36-2, 3-Amino-5-chloro-2-hydroxypyridine, 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: 98027-36-2, blongs to pyridine-derivatives compound. Recommanded Product: 98027-36-2

(Reference Example 8-2) To a 1,2-dichloroethane suspension (177 ml) of 3-amino-5-chloropyridin-2-ol (8.85 g) and tert-butyl 4-oxopiperidine-1-carboxylate (24.4 g) was added sodium triacetoxyborohydride (26.0 g), followed by stirring under heating at reflux for 4 hours. Tert-butyl 4-oxopiperidine-1-carboxylate (12.4 g) and sodium triacetoxyborohydride (13.7 g) were further added, and stirred under heating at reflux for 2 hours. After the reaction solution was brought back to room temperature, water and dichloromethane were added, and the solution was separated. The organic layer was dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to afford tert-butyl 4-[(5-chloro-2-hydroxypiperidin-3-yl)amino]piperidine-1-carboxylate (12.7 g). 1H NMR (400 MHz, CDCl3) delta 1.43-1.50 (m, 2H), 1.47 (s, 9H), 2.00-2.03 (m, 2H), 2.95-3.01 (m, 2H), 3.32-3.35 (m, 1H), 4.03-4.06 (m, 2H), 4.98-5.00 (m, 1H), 6.25 (d, 1H, J = 2.4 Hz), 6.71 (d, 1H, J = 2.4 Hz), 12.37 (br s, 1H).

The synthetic route of 98027-36-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Daiichi Sankyo Company, Limited; EP2471792; (2012); 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. 153813-70-8, name is 3-Nitroisonicotinaldehyde, the common compound, a new synthetic route is introduced below. SDS of cas: 153813-70-8

A mixture of 3-nitropyridine-4-carboxaldehyde (1.50 g, 9.86 mmol), N-Boc-piperidine-3,5-dione (2.52 g, 11.83 mmol) and iron (2.75 g, 49.3 mmol) in acetic acid (50 mL) was heated at 50C for 3h. The mixture was concentrated in vacuo. The solution was co-evaporated twice with toluene. The residue was dissolved in AcOEt and a saturated solution of NaHCO3. The mixture was filtered over celite. The layers of the filtrate was separated. The aqueous layer was extracted with AcOEt. The organic layers were combined, dried over Na2SO4, filtered and concentrated in vacuo. Acetone (20 mL) was added to the residue and the mixture refluxed for 30min. The mixture was cooled at rt and filtrated to provide intermediate ( 5a) as an off-white solid (1.21 g, 4.01 mmol, 40%). MS m/z ([M+H]+) 302. 1H NMR (400 MHz, DMSO-d6): delta (ppm) 1.43 (s, 9H), 3.55 (s, 2H), 3.94 (s, 2H), 4.29 (s, 2H), 7.13 (d, J = 4.9 Hz, 1H), 7.91-8.19 (m, 2H), 9.76 (s, 1H).

The synthetic route of 153813-70-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Mutabilis; BARBION, Julien; CARAVANO, Audrey; CHASSET, Sophie; CHEVREUIL, Francis; LECOINTE, Nicolas; LE STRAT, Frederic; OLIVEIRA, Chrystelle; SIMON, Christophe; (44 pag.)EP3604309; (2020); 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.88579-63-9, name is 2,6-Dichloropyridine-4-methylamine, molecular formula is C6H6Cl2N2, molecular weight is 177.0312, as common compound, the synthetic route is as follows.name: 2,6-Dichloropyridine-4-methylamine

[0918] A mixture of(28,58)-1-[(4-fluorobenzene)sulfonyl]-5-methylpynolidine-2-carboxylic acid (3 g, 10.44 mmol, 1.00 equiv), HATU (4.7 g, 12.36 mmol, 1.20 equiv), DIEA (2.6 g, 20.12 mmol, 2.00 equiv), and (2,6-dichloropyridin-4-yl)methanamine (2 g, 11.30 mmol, 1.10 equiv) in N,Ndimethylformamide (100 mL) was stirred for 1 h at room temperature. The resulting solution was diluted with ethyl acetate, washed with brine, dried over anhydrous sodium sulfate, and concentrated under vacuum. The residue was purified by a silica gel colunm eluting with ethyl acetate/petroleum ether (1:1) to afford the title compound (3.6 g, 77%) as yellow oil. LCMS [M+H] 446.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,88579-63-9, 2,6-Dichloropyridine-4-methylamine, and friends who are interested can also refer to it.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; ESTRADA, Anthony; VOLGRAF, Matthew; CHEN, Huifen; KOLESNIKOV, Aleksandr; VILLEMURE, Elisia; VERMA, Vishal; WANG, Lan; SHORE, Daniel; DO, Steven; YUEN, Po-wai; HU, Baihua; WU, Guosheng; LIN, Xingyu; LU, Aijun; (537 pag.)WO2016/128529; (2016); 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 131747-53-0, name is (6-(Trifluoromethyl)pyridin-2-yl)methanol. This compound has unique chemical properties. The synthetic route is as follows. Product Details of 131747-53-0

3.78 g of carbon tetrabromide and 2.78 g of triphenylphosphine were added to a solution containing 1.70 g of the (6-trifluoromethylpyridin-2-yl) methanol obtained in (4) dissolved in 30 ml of methylene chloride followed by stirring for 1 hour at room temperature. 30 ml of acetonitrile, 1.52 g of N-(t-butoxycarbonyl) hydroxylamine and 1.74 g of 1,8-diazabicyclo[5.4.0]-7-undecene (DBU) were added to this reaction solution followed by stirring for 3 hours at room temperature. Following completion of the reaction, aqueous ammonium chloride solution was added to the reaction mixture followed by extraction with ethyl acetate. The ethyl acetate layer was dried by addition of anhydrous magnesium sulfate followed by filtration and distilling off the solvent from the filtrate under reduced pressure. The resulting residue was purified by silica gel column chromatography (developing solvent; n-hexane:ethyl acetate = 3:1 (volume ratio)) to obtain 1.54 g of the target compound of t-butyl N-[(6-trifluoromethylpyridin-2-yl)methyloxy] carbamate (yield: 59%). [1H-NMR Data of t-Butyl N-[(6-trifluoromethylpyridin-2-yl)methyloxy] Carbamate 1H-NMR (CDCl3/TMS, delta ppm): 7.90(dd,1H), 7.73(d,1H), 7.62(d,1H), 7.44(bs,1H), 1.48(s,9H)

With the rapid development of chemical substances, we look forward to future research findings about 131747-53-0.

Reference:
Patent; Nippon Soda Co., Ltd.; EP2218711; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 62674-71-9, name is 2-Iodo-6-methylpyridine, molecular formula is C6H6IN, 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. Quality Control of 2-Iodo-6-methylpyridine

A mixture of Compound la (55 mg, 0.171 mmol) 2-bromo-6-methylpyridine (23.4 ul, 0.205 mmol), tetrakis(triphenylphosphine)palladium (7.89 mg, 0.007 mmol), sodium acetate (28 mg, 0.342 mmol) and tetrabutylammonium fluoride (44.7 mg, 0.17 1 mmol)) in anhydrous DMF (3 mL) was heated at 110°C into a microwave oven (Biotage Smith Creator®) for 10 mm then cooled at r.t.. The reaction mixture was poured into water and extracted with EtOAc (3x). The organic layer was dried over Na2504 and the solvent was evaporated to dryness to give a crude which was purified via automated flashchromatography (SP1® Biotage, SNAP25 Cartridge), eluting with a EtOAc – PetroleumEther gradient from 75:25 to 1:1 to give mg 51(87.6percent) of the title compound.UPLC-MS [M+H]= 341.521H NMR (400 MHz, DMSO-d6) oe ppm 7.68 (t, 1 H), 7.31 (d, 1 H), 7.22 (d, 1 H), 5.66 (s,1 H), 3.43 (brt, 2 H), 3.15 (s, 2 H), 2.62 (brt, 2 H), 2.45 (s, 3 H), 1.42 (s, 9 H), 1.08 (s, 6H)

With the rapid development of chemical substances, we look forward to future research findings about 62674-71-9.

Reference:
Patent; RECORDATI INDUSTRIA CHIMICA E FARMACEUTICA SPA; RIVA, Carlo; GRAZIANI, Davide; LONGHI, Matteo; CALLEGARI, Elisa; FRIGERIO, Fabio; ANGELICO, Patrizia; (197 pag.)WO2019/2571; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 59942-87-9, 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 59942-87-9, name is Pyrazolo[1,5-a]pyridin-2(1H)-one. This compound has unique chemical properties. The synthetic route is as follows.

EXAMPLE 3 FOR REFERENCE Synthesis of 2-methoxypyrazolo[1,5-a]pyridine Sodium (92 mg) was dissolved in 5 ml of absolute methyl alcohol with moderate cooling. To this solution 2-hydroxypyrazolo[1,5-a]pyridine (500 mg) was added and then dimethyl sulfate (500 mg) was added. The mixture was stirred for 30 min. at room temperature and refluxed for 8 hr. The reaction mixture was concentrated to remove methyl alcohol, and water was added to the residue. The solution was extracted with n-hexane, and the n-hexane solution was dried over sodium sulfate. The dried n-hexane solution was concentrated and the residue was distilled to give 280 mg of oily product under reduced pressure.

According to the analysis of related databases, 59942-87-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Kyorin Pharmaceutical Co., Ltd.; US4028370; (1977); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 912369-42-7, name is Methyl 3-((tert-butoxycarbonyl)amino)picolinate, molecular formula is C12H16N2O4, 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. Application In Synthesis of Methyl 3-((tert-butoxycarbonyl)amino)picolinate

ter f-butyl f2-(hvdroxymethyl)py ridin-3-yll carbamate; To methyl 3-[(tert- butoxycarbonyl)amino]pyridine-2-carboxylate and methyl 2-[(tert- butoxycarbonyl)amino]nicotinate (5.00 g, 19.8 mmol) is added THF/MeOH (30 mL/3 mL) and the reaction is cooled to 0 C whereupon sodiumborohydride (1.49 g, 39.6 mmol) is added. The reaction is warmed to rt and stirred for four hours. The reaction mixture is then EPO dissolved in EtOAc and washed with saturated sodium bicarbonate solution. The organic layers are combined, dried over magnesium sulfate, filtered, and concentrated under reduced pressure to afford the title compound and tert-buty [3-(hydroxymethyl)pyridin-2- yljcarbamate which are separated by preparatory HPLC (5-95% MeCN/water/0.1% TFA). The desired isomer is confirmed by ID NOE NMR experiments. 1H NMR delta 8.78 (br s, IH), 8.17 (m, IH), 8.10 (d, IH), 7.27 (dd, IH), 4.64 (s, 2H), 1.46 (s, 9H). LCMS (ES, M+H=225).

With the rapid development of chemical substances, we look forward to future research findings about 912369-42-7.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2006/106326; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 886364-94-9, name is 5-Bromo-4-methylpicolinaldehyde, molecular formula is C7H6BrNO, 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. Application In Synthesis of 5-Bromo-4-methylpicolinaldehyde

To a solution of 5-bromo-4-methylpicolinaldehyde (1.044 g, 5.22 mmol) in MeOH (20.0 ml) was added 2.0 M methylamine in MeOH (8.0 ml, 16.00 mmol) followed by sodium cyanoborohydride (1.313 g, 20.89 mmol) and acetic acid (1.00 ml, 17.47 mmol). After stirring at room temperature for 90 mins, the reaction was quenched with HCl (6.0 N in water) (25.0 ml, 150 mmol). The mixture was stirred at room temperature for 30 mins, and treated with NaOH (4 N in water) until pH reached 10. The mixture was extracted with Et2O. The organic layer was dried over anhydrous Na2SO4, filtered and concentrated. The residue was dissolved in CH2Cl2 (30 mL), and treated with Boc-anhydride (1.198 g, 5.49 mmol). After stirring at room temperature for 30 mins, the reaction was concentrated. The residue was purified on silica gel (40 g, 0-100percent EtOAc in hexanes) to give the desired product as a yellow oil (1.101 g, 67percent). LCMS calculated for C13H20BrN2O2 (M+H)+ m/z=315.1; found 315.0.

With the rapid development of chemical substances, we look forward to future research findings about 886364-94-9.

Reference:
Patent; Incyte Corporation; Vechorkin, Oleg; Liu, Kai; Pan, Jun; Sokolsky, Alexander; Ye, Hai Fen; Ye, Qinda; Yao, Wenqing; Hummel, Joshua; (117 pag.)US2018/72741; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem