Day: April 11, 2022

Synthetic Route of 127446-34-8 , The common heterocyclic compound, 127446-34-8, name is N-(6-Chloro-3-formylpyridin-2-yl)pivalamide, molecular formula is C11H13ClN2O2, 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.

Step 1 : Sodium thiomethoxide (1 .37 g, 19.5 mmol, 1 .50 eq) is added to N-(6-chloro-3-formyl- pyridin-2-yl)-2,2-dimethyl-propionamide (Org Process Res. Dev. 2009, 13, 555) (1 .87 g, 7.79 mmol) in THF (50 mL) in a round-bottom flask and the solution is stirred at 50 C for 2 h. The reaction mixture is diluted with EtOAc and washed with brine. The organic layer is dried over MgS04, filtered and concentrated under reduced pressure to afford intermediate 5001 A.

The synthetic route of 127446-34-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; FADER, Lee; LEPAGE, Olivier; BAILEY, Murray; BEAULIEU, Pierre Louis; BILODEAU, Francois; CARSON, Rebekah; GIROUX, Andre; GODBOUT, Cedrickx; MOREAU, Benoit; NAUD, Julie; PARISIEN, Mathieu; POIRIER, Martin; POIRIER, Maude; SURPRENANT, Simon; THIBEAULT, Carl; WO2013/152063; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 58539-65-4, 2-Methylnicotinamide, 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: 58539-65-4, blongs to pyridine-derivatives compound. Recommanded Product: 58539-65-4

Oxalyl chloride (1.90 mL, 21.8 mmol) was added to 2-methyl nicotinic acid (1.50 g, 10.9 mmol) in anhydrous dichloromethane (20 mL) with triethylamine (1.6 mL, 11.5 mmol) and the reaction mixture was kept at room temperature overnight before the solvent was removed. THF was added to the residue and ammonia gas was bubbled through for 2 h. The THF was removed and the residue was dissolved into methanol and water and the pH was adjusted to 10.0 with potassium carbonate. The mixture was concentrated. After column chromatography the desired amide was isolated (1.10 g, 73.8%).NaH (0.428 g, 10.7 mmol, 60% in mineral oil) was added to 4-hydroxy-3,5-dimethylbenzonitrile (1.50 g, 10 mmol) in anhydrous DMF (8 mL). Benzyl bromide (1.83 g, 10.7 mmol) was added and the reaction was kept at room temperature overnight. The reaction mixture was poured into water. The isolated solid was further washed with hexane to yield the desired ether building block (2.0 g, 84.3%). It was used in the next reaction without further purification. The above amide (0.65 g, 4.77 mmol) in anhydrous THF (15 mL) was added drop-wise to BuLi (7.5 mL, 1.60 M) at -20 C. The reaction mixture was kept at this temperature for 1 h and then the above ether building block (1.13 g, 4.77 mmol) in THF (20 mL) was added drop-wise at -20 C. and the reaction was stirred for 1.5 h. The reaction temperature was increased to room temperature and continued for a further 1 h. Water (20 mL) was added and the mixture was stirred for a while before the solvent was removed and the residue was purified by column chromatography to yield the desired intermediate (0.50 g, 29.4%). A 50 mL flask was charged with the above described intermediate (0.50 g, 0.0014 mol) and pyridine hydrogen chloride (2.4 g, 0.014 mol) and the mixture was heated to 180 C. for 1.5 h. The mixture was cooled and poured into methanol (4 mL), then filtered. The collected solid was further washed with ethyl acetate and dried to give 7-(4-hydroxy-3,5-dimethylphenyl)-1,6-naphthyridin-5(6H)-one (350 mg, 82.7%) as an HCl salt. Selected data: MS (ES) m/z: 266; MP>350 C.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,58539-65-4, 2-Methylnicotinamide, and friends who are interested can also refer to it.

Reference:
Patent; Wong, Norman C.W.; Tucker, Joseph E.L.; Hansen, Henrik C.; Chiacchia, Fabrizio S.; McCaffrey, David; US2008/188467; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 885168-04-7, 5-Bromo-3-chloropicolinaldehyde, 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, category: pyridine-derivatives, blongs to pyridine-derivatives compound. category: pyridine-derivatives

To a stirred solution of 5-bromo-3-chloropicolinaldehyde (8.5 g, 38.6 mmol, I eq) in THE(135 mL) was added allylbromide (5.0 mL, 90.6 mmol, 1.5 eq) and sat. NH4CI solution followed by zinc dust (5.0 g, 77.3mmol, 2 eq) . After complete addition the RM was stirred for 2 h at RT .Then the RM was diluted with water (100 mL) and extracted with EtOAc (3×100 mL) , dried over anhydr. Na2SO4 and evaporated under reduced pressure to give crude product which was purified by CC to afford 1-(5-bromo-3-chloropyridin-2- yl)but-3-en-1-ol(4.5 g, 44%) as an off white solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,885168-04-7, 5-Bromo-3-chloropicolinaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; GRUeNENTHAL GMBH; SCHUNK, Stefan; REICH, Melanie; JAKOB, Florian; DAMANN, Nils; HAURAND, Michael; KLESS, Achim; ROGERS, Marc; SUTTON, Kathy; WO2015/158427; (2015); 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. 139585-48-1, name is 2-Chloro-5-methoxypyridine. A new synthetic method of this compound is introduced below., HPLC of Formula: C6H6ClNO

A solution of 5-(tributylstannyl)thiazole (295 mg, 0.788 mmol) and 2-chloro-5-methoxypyridine (75 mg, 0.526 mmol) in toluene (2.0 mL) was degassed with argon for 3 min. Pd(PPh3)4 (24.29 mg, 0.021 mmol) was added. The reaction mixture was sealed and heated in an oil bath at 105 C for 4 h. After being cooled to room temperature, the reaction mixture was directly loaded on a column for purification. The crude product was purified by flash chromatography (loading in chloroform, 0% to 85% EtOAc in hexane over 10 min using a 4 g silica gel cartridge). The desired fractions were combined and concentrated to yield Intermediate 52A (70 mg, 0.364 mmol, 69.3 % yield) as a white solid.1H NMR (400MHz, METHANOL-d4) delta 8.94 (s, 1H), 8.26 (s, 1H), 8.19 (d, J=2.9 Hz, 1H), 7.75 (d, J=8.6 Hz, 1H), 7.36 (did, J=8.7, 3.0 Hz, 1H), 3.88 (s, 3H); LC^MS: method C, RT = 0.64 min, MS (ESI) m/z: 193.3 (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, 139585-48-1, 2-Chloro-5-methoxypyridine.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; RICHTER, Jeremy M.; ZHANG, Xiaojun; PRIESTLEY, Eldon Scott; (111 pag.)WO2018/13772; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 188577-69-7, 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 188577-69-7, name is 3,4-Dichloropyridin-2-amine. This compound has unique chemical properties. The synthetic route is as follows.

2,7,8-Trichloro-imidazo[1,2-a]pyridine (17). 2-Amino-3,4-dichloropyridine, compound 5 (1.0 g, 6.1 mmol) was treated with ethyl bromoacetate (5.0 mL, 45.0 mmol) at 60 C. for 24 hours to give a white solid. This solid was removed by filtration, dissolved in water, treated with ion exchange resin and chlorinated with POCl3 as described above to give, after purification by flash chromatography (EtOAc/hexane 1:2, 15 cm*4 cm) and recrystallization from MeOH, 700 mg (52%) of compound 17 as white crystals. Compound 17: mp 220-221 C.; Rf 0.29 (EtOAc/hexane 1:2); 1H-NMR (360 MHz, CDCl3) delta7.93 (d, 1H J=7.15 Hz), 7.56 (s, 1H), 6.94 (d, 1H, J=7.15 Hz); 13C-NMR (90 MHz CDCl3) delta141.77 (C8a), 137.20 (C2), 129.87 (C7), 123.52 (C5), 121.30 (C8), 115.08 (C6), 110.39 (C3); UV lambdaax (EtOH) 304 (5250), 288 (5825), 233 (10434); (pH 11) 287 (6566), 232 (24612); (pH 1) 287 (8865), 231 (26610); HRMS m/z calcd for C7H3Cl3N2 219.9362, found 219.9355. Anal. Calcd for C7H3Cl3N2.1/4 H2O: C, 37.21; H, 1.56; N, 12.40. Found: C, 37.40; H, 1.46; N, 12.22.

According to the analysis of related databases, 188577-69-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; The Regents of the University of Michigan; US6214801; (2001); B1;,
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.103058-87-3, name is 5-Bromo-2-methoxynicotinaldehyde, molecular formula is C7H6BrNO2, molecular weight is 216.032, as common compound, the synthetic route is as follows.Application In Synthesis of 5-Bromo-2-methoxynicotinaldehyde

5-Bromo-2-methoxynicotinaldehyde (0.529 g, 2.450 mmol) and (2S,3S,4S,5S)-tert-butyl 4-amino-3-(tert-butyl)-1-(cyclohexanecarbonyl)-5-phenylpyrrolidine-2-carboxylate (Example 25B, 1 g, 2.333 mmol) were mixed in methanol (12 mL), and the reaction was stirred at room temperature for 1 hour. Sodium cyanoborohydride (0.740 g, 11.78 mmol) was then added in one portion, and the reaction continued to stir at room temperature for 1.5 days. After this time, the solvent was removed in vacuo, and the residue was taken up in 100 mL water and 100 mL CH2Cl2 and transferred to a separatory funnel. The separatory funnel was shaken, the phases were separated, and the aqueous layer was extracted twice more with CH2Cl2 (100 mL each time). The combined organics were dried over Na2SO4, filtered, and concentrated in vacuo. Silica gel chromatography, eluting with 5 to 30% ethyl acetate-heptanes, provided the impure title compound, 1.02 g. The material was taken directly into the next reaction without additional purification. 1H NMR (400 MHz, dimethyl sulfoxide-d6) delta ppm 8.00 (m, 1H), 7.59 (m, 2H), 7.40-7.19 (m, 4H), 5.17 (d, J=6.9 Hz, 1H), 4.40 (d, J=2.7 Hz, 1H), 3.68 (s, 3H), 3.41-3.21 (m, 3H), 2.26 (m, 1H), 2.19 (m, 1H), 1.68-1.02 (m, 10H), 1.43 (s, 9H), 0.98 (s, 9H); MS (ESI+) m/z 628.0 (M+H)+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,103058-87-3, 5-Bromo-2-methoxynicotinaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; AbbVie S.a.r.l.; Galapagos NV; Altenbach, Robert J.; Bogdan, Andrew; Couty, Sylvain; De Lemos, Elsa; Desroy, Nicolas; Duthion, Beranger; Gfesser, Gregory A.; Greszler, Stephen N.; Housseman, Christopher Gaetan; Koenig, John R.; Kym, Philip R.; Liu, Bo; Scanio, Marc J.; Searle, Xenia; Wang, Xueqing; Yeung, Ming C.; Zhao, Gang; (263 pag.)US2018/99931; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 271-29-4, 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.271-29-4, name is 1H-Pyrrolo[2,3-c]pyridine, molecular formula is C7H6N2, molecular weight is 118.14, as common compound, the synthetic route is as follows.

To a solution of 1H-pyrrolo[2,3-c]pyridine (1 g, 8.47 mmol) in H2S04 (5 mL) was added 69% HNO3 (533 mg, 8.47 mmol) at 0 C. After stirred at 0 C for 2 hrs, the reaction mixture was allowed to warm to room temperature and stirred overnight. The mixture was then poured into H20 (100 mL) and basified by NaOH powder to pH> 7. Then the mixture was extracted by EA (100 mL x3), dried over anhydrous Na2SO4, and evaporated in vacuum to afford 3-nitro-1H- pyrrolo[2,3-c]pyridine (690 mg, 50%) as a yellow solid. ?H NIVIR (400 IVIHz, DMSO-d6): oe = 8.94 (s, 1H), 8.85 (s, 1H), 8.44 (d, J= 5.2 Hz, 1H), 8.02 (dd, J= 5.6, 1.2 Hz, 1H). MS: m/z 164.0 (M+H).

The chemical industry reduces the impact on the environment during synthesis 271-29-4, I believe this compound will play a more active role in future production and life.

Reference:
Patent; SANFORD BURNHAM PREBYS MEDICAL DISCOVERY INSTITUTE; GARDELL, Stephen; PINKERTON, Anthony B.; SERGIENKO, Eduard; SESSIONS, Hampton; (428 pag.)WO2018/132372; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1192472-59-5, 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.1192472-59-5, name is tert-Butyl (5-ethynylpyridin-3-yl)carbamate, molecular formula is C12H14N2O2, molecular weight is 218.25, as common compound, the synthetic route is as follows.

Step D: tert-Butyl [5-({2-[(tert-butoxycarbonyl)amino]-5-cyanophenyl}ethynyl)pyridin-3-yl]carbamate Into a reaction flask were added tert-butyl (4-cyano-2-iodophenyl)carbamate (1.4 g, 4.1 mmol), copper(I) iodide (31 mg, 0.16 mmol), bis(triphenylphosphine)palladium(II) chloride (0.12 g, 0.16 mmol), tetrahydrofuran (10 mL), and triethylamine (0.63 mL, 4.5 mmol). The mixture was stirred under N2 bubbling for 5 minutes and tert-butyl (5-ethynylpyridin-3-yl)carbamate (0.90 g, 4.1 mmol) (prepared according to Example 17, Step B) was then added. The reaction mixture was stirred at 65 C. for 2 hours. The solvent was removed under vacuum and the residue was diluted with EtOAc and water. After separation, the organic layer was dried over Na2SO4 and concentrated under vacuum. The crude was purified by silica gel column chromatography to give the desired product (0.94 g, 52%). LCMS for C24H27N4O4 (M+H)+: m/z=435.2.

The chemical industry reduces the impact on the environment during synthesis 1192472-59-5, I believe this compound will play a more active role in future production and life.

Reference:
Patent; INCYTE CORPORATION; US2010/190804; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 161117-83-5, Adding some certain compound to certain chemical reactions, such as: 161117-83-5, name is tert-Butyl (2-methoxypyridin-3-yl)carbamate,molecular formula is C11H16N2O3, 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 161117-83-5.

EXAMPLE 2 Ketone 2-1 To a -70 C. solution of 1.12 g (5.0 mmol) of 3-(N-tert-butoxycarbonylamino)-2-methoxypyridine (Kelly, Tetrahedron Lett. 35 (48), 1994, 9003-9006) in 25 mL of dry ether was added 1.8 mL (12.0 mmol) TMEDA followed by 4.8 mL (12.0 mmol) of n-BuLi. The resulting solution was warmed to -15 C. where it was aged for 2 h. The reaction mixture was recooled to -70 C. and treated with 0.83 mL (7.0 mmol) of ethyl trifluoroacetate. After stirring an additional 3 h, the reaction was quenched with 25 mL of saturated NH4Cl solution and the two phases were separated. The aqueous phase was extracted with 100 mL of EtOAc and the combined organic extracts were washed with 25 mL of brine and dried over MgSO4. The yellow solution was concentrated and chromatographed (CH2Cl2) to afford trifluoromethyl ketone 2-1. 1H NMR (CDCl3) delta 7.95 (d, J=8 Hz, 1H), 7.10 (bs, 1H), 6.95 (d, J=8 Hz, 1H), 4.05 (s, 3H), 1.50 (s, 9H).

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. 161117-83-5, tert-Butyl (2-methoxypyridin-3-yl)carbamate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Merck & Co., Inc.; US6239132; (2001); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 55052-27-2 ,Some common heterocyclic compound, 55052-27-2, molecular formula is C7H5ClN2, 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 solution of 6-chloro-1H-pyrrolo[2,3-b]pyridine (1 .37 g, 8.97 mmol) in DMF (100 ml_), sodium hydride (60 % in paraffin, 1 g, 41 mmol) was added. The solution was stirred for 30 min being allowed to warm up from 0 C to rt. Subsequently, benzenesulfonic acid chloride (1 .5 mL, 1 1.8 mmol) was added dropwise. The suspension was stirred 3 h at room temperature and hydrolyzed with ice water. The resulting solid was filtered off under reduced pressure, washed thoroughly with water (75 mL) and finally with petroleum ether (15 mL). The resulting material was dried at 60 C and purified by column chromatography (eluent: pure dichloromethane) yielding 856 mg of 1 -(benzenesulfonyl)-6-chloro- pyrrolo[2,3-b]pyridine Xll-4a as a brownish solid. (1073) Yield: 32%

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. 55052-27-2, 6-Chloro-1H-pyrrolo[2,3-b]pyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; UCB PHARMA GMBH; PEGURIER, Cecile; PROVINS, Laurent; CARDENAS, Alvaro; LEDECQ, Marie; MUELLER, Christa E.; HOCKEMEYER, Joerg; EL-TAYEB, Ali; BOSHTA, Nader; RASHED, Mahmoud; (165 pag.)WO2019/243303; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem