Tag: M.W:200-300

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

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

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

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

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

Application of 89282-03-1, 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. 89282-03-1, name is 3-Iodopyridin-4-ol, molecular formula is C5H4INO, 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.

3-Iodo-4-hydroxypyridine (0.500 g, 2.250 mmol) was reacted with allyl bromide (0.409 g, 3.380 mmol), potassium carbonate (0.780 g, 5.630 mmol) and potassium iodide (0.016 g, 0.100 mmol) in acetone (20 mL) at reflux temperature for 2 h. Then reaction mixture was cooled to room temperature, filtered and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (hexanes/ethyl acetate = 90/10) to get the title compound (0.400 g, 67%) as a liquid. LCMS: nt/z 261.9 [M+l] +; NMR (300 MHz, DMSO-d6) delta 7.86-7.85 (d, / =2.4Hz, 1H), 7.31-7.28 (m, 1H), 6.41-6.38 (d, / =7.2 Hz, 1H), 5.97-5.86 (m, 1H), 5.43-5.40 (dd, / =9.6, 1.5 Hz, 1H), 5.29-5.25 (dd, / = 10.8, 1.0 Hz, 1H), 4.40-4.38 (m, 2H).

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 89282-03-1, 3-Iodopyridin-4-ol.

Reference:
Patent; AURIGENE DISCOVERY TECHNOLOGIES LIMITED; CHIKKANNA, Dinesh; KHAIRNAR, Vinayak; (74 pag.)WO2016/12958; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 69045-78-9, 2-Chloro-5-(trichloromethyl)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: 2-Chloro-5-(trichloromethyl)pyridine, blongs to pyridine-derivatives compound. Recommanded Product: 2-Chloro-5-(trichloromethyl)pyridine

2000 kg of 2-chloro-5-trichloromethylpyridine was placed in a glass-lined chlorination kettle.Then adding catalyst to the reactorThe 150kg reactor is heated with a heat transfer oil.When the temperature rises to 130 C, chlorine gas is introduced into the reactor to control the amount of chlorine.The reaction temperature was controlled at 180 C. The reaction time is usually 100 hours.After the reaction is completed, the temperature is lowered to 50 C, and the catalyst is filtered off.After the 2,3-dichloro-5-trichloromethylpyridine was metered, it was fluorinated in a fluorination kettle.

The synthetic route of 69045-78-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shandong Huimeng Biological Technology Co., Ltd.; Xiao Caigen; Liu Shuwen; (7 pag.)CN107935920; (2018); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 850429-51-5, 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. 850429-51-5, name is Ethyl 6-amino-5-bromonicotinate, molecular formula is C8H9BrN2O2, 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) To a solution of ethyl 6-amino-5-bromonicotinate (2.31 g, 10 mmol) in tetrahydrofuran (20 mL) at RT was added LAH (10 mL, IM in tetrahydrofuran) dropwise. After stirring for Ih, the mixture was quenched with water (0.2 mL) and the resultant precipitate was filtered and washed with ethyl acetate. The filtrate was concentrated in vacuo to afford (6-amino-5-bromopyridin-3-yl)methanol (2.0 g, 99%) as a solid. LC/MS; (M+H)+ = 203, 205 (1 : 1 ratio). 1H NMR (CD3OD, 300 MHz) delta 7.79 (s, IH), 7.67 (s, IH), 4.35 (br S, 2H).

According to the analysis of related databases, 850429-51-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2008/60907; (2008); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 17570-98-8, 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.17570-98-8, name is 2-(Bromoacetyl)pyridine hydrobromide, molecular formula is C7H7Br2NO, molecular weight is 280.95, as common compound, the synthetic route is as follows.

7V,/V-dicyclopropyl-6-ethyl-l-methyl-4-(4-(pyridin-2-yl)thiazol-2-ylamino)-l,6- dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridine-7-carboxamide [00183] A solution of 4-amino-N,N-dicyclopropyl-6-ethyl-l -methyl- 1,6- dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridine-7-carboxamide (example 1J, 70 mg, 0.21 mmol) and benzoyl isothiocyanate (36 mu, 0.27 mmol) in acetone (1 ml) was stirred at room temperature for 1.5h. The solvent was removed in vacuo, the residue was taken up in EtOH (1.5 ml), and K2CO3 (40 mg, 0.290 mmol) was added. The reaction was heated at 60C for 3h. Upon cooling to room temperature, 2-bromo-l- (pyridin-2-yl)ethanone, hydrobromide (139.4 mg, 0.50 mmol) was added and the reaction heated at 80C for 24h. The reaction mixture was cooled to roomtemperature and concentrated. The residue was purified by silica gel chromatography (0-7% MeOH/dichloromethane). Re-purification by preparative HPLC provided 10.2 mg (10% yield) of N,N-dicyclopropyl-6-ethyl-l -methyl -4-(4-(pyridin-2-yl)thiazol-2- ylamino)-l,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridine-7-carboxamide as a brown solid.[00184] MS (ESI) rt = 1.78 min, m/z 499 (M+H).[00185] 1H MR (DMSO-d6) delta ppm 10.9 (s, 1 H), 8.2 (bs, 1 H), 7.81 (d, 1 H), 7.75 (s, 1H), 3.92 (m, 4H), 3.77 (q, 2H, J= 7.8 Hz), 2.52-2.81 (m, 7H).

Statistics shows that 17570-98-8 is playing an increasingly important role. we look forward to future research findings about 2-(Bromoacetyl)pyridine hydrobromide.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; PURANDARE, Ashok V.; GREBINSKI, James W.; HART, Amy; INGHRIM, Jennifer; SCHROEDER, Gretchen; WAN, Honghe; WO2011/28864; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 22282-70-8 ,Some common heterocyclic compound, 22282-70-8, molecular formula is C5H3FIN, 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.

Reference Example 2; 4-iodopyridin-2-amine2-Fluoro-4-iodopyridine (11.2 g, 50 mmol) obtained in Reference Example 1 and 28% aqueous ammonia solution (100 ml) were stirred at 150 C. for 3 hr in a sealed tube. The mixture was extracted with ethyl acetate. The extract was washed with water, and dried over anhydrous sodium hydrogensulfate. The solvent was evaporated under reduced pressure. The obtained residue was crystallized from ethyl acetate to give the title compound (6.6 g, yield 60%). melting point 167-168 C.1H-NMR (CDCl3) delta: 4.34 (2H, brs), 6.92 (1H, d, J=1.4 Hz), 6.99 (1H, dd, J=5.5, 1.4 Hz), 7.73 (1H, d, J=5.5 Hz).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,22282-70-8, its application will become more common.

Reference:
Patent; Takeda Pharmaceutical Company Limited; US2011/39893; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem