Month: June 2021

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. 100367-40-6, name is 2-Amino-5-bromo-4-methyl-3-nitropyridine. This compound has unique chemical properties. The synthetic route is as follows. Quality Control of 2-Amino-5-bromo-4-methyl-3-nitropyridine

Thereafter, this compound is then reacted with sodium nitrite (NaN02) andtrimethylsilyl chloride (T -C1) in methanol (MeOH) to yield .

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, 100367-40-6, 2-Amino-5-bromo-4-methyl-3-nitropyridine.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; TRIPP, Jonathan Clive; FANFAIR, Dayne Dustan; SCHULTZ, Mitchell J.; MURUGESAN, Saravanababu; FOX, Richard J.; CHEN, Chung-Pin H.; IVY, Sabrina E.; PAYACK, Joseph Francis; DOUBLEDAY, Wendel W.; WO2012/106189; (2012); 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.609-71-2, name is 2-Oxo-1,2-dihydropyridine-3-carboxylic acid, molecular formula is C6H5NO3, molecular weight is 139.1088, as common compound, the synthetic route is as follows.COA of Formula: C6H5NO3

Preparation 49 5-Bromo-2-hydroxy-3-pyridinecarboxylic acid To a solution of 10 g (0.07 mole) of 2-hydroxy-nicotinic acid in 16.8 g of 50% sodium hydroxide (0.21 mole) diluted with 25 ml of water was added 200 ml of sodium hypobromite solution prepared by adding 13.6 g (0.17 mole) of bromine to a solution of 20.16 g of 50% sodium hydroxide (0.25 mole) in 125 ml of water at 0 C. diluted to 400 ml. After 24 hrs of stirring at room temperature, another 100 ml portion of the above sodium hypobromite solution was added and the reaction solution was stirred for another 24 hr. The reaction solution was cooled in an ice bath and acidified carefully with 12N hydrochloric acid. Crystallization from isopropyl alcohol gave 9.7 g (63.5%) of product. A sample was further recrystallized from 95% ethanol, m.p. 245 C. Analysis: Calculated for C6 H4 NO3: C, 33.06; H, 1.85; N, 6.42. Found: C, 32.98; H, 1.83; N, 6.44.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,609-71-2, 2-Oxo-1,2-dihydropyridine-3-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; A. H. Robins Company, Inc.; US4592866; (1986); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1594-57-6 ,Some common heterocyclic compound, 1594-57-6, molecular formula is C6H7N3O, 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 4- (Boc-aminomethyl)-benzoic acid (187 mg) in DMF (0.25 M) were added DIEA (5 eq), TBTU (1 eq) and HOBt (0.2 eq). The solution was stirred at RT for 3 minutes, and then isonicotinamide oxime (102mg, 1 eq) was added. After 1 hour, the solvent was evaporated. The residue was triturated with 0.05 M NaOH (5 ml). The solid was filtered off, washed with water and dried under vacuum. The solid was dissolved in DMF (0.25 M). The reaction mixture was heated at 110C for 2 hours. The reaction mixture was cooled down at RT. The precipitate was filtered off, washed with water, and then dried under vacuum. The solid was dissolved in 3N HCI. The solution was heated at 50C for 2 hours. The solvent was evaporated and the residue was dried under vacuum. The title product was obtained as a white powder (74% yield).’H NMR (300 MHz, DMSO-d6): 4.15 ppm (q, 2H, J=5.7 Hz); 5.00 ppm (bs, 2H); 7.80 ppm (d, 2H, J=8.4 Hz); 8.24 ppm (m, 4H); 8.95 ppm (d, 2H, J=6.0 Hz).

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. 1594-57-6, N-Hydroxyisonicotinimidamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; DEVGEN NV; WO2005/82367; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1186608-83-2, 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. 1186608-83-2, name is 3-Bromo-5-nitro-1H-pyrazolo[3,4-b]pyridine, molecular formula is C6H3BrN4O2, 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.

40% Dimethyl amine in water (2.6 mL, 21 mmol) was added to a solution of 3-bromo-5-nitro-lH-pyrazolo[3,4-b]pyridine (0.063 g, 0.26 mmol) in DMF (6.0 mL), and the mixture was placed in a microwave reactor at 1400C for 15 hours. The reaction mixture was diluted with ethyl acetate (100 mL), and the organic layer was washed with water (3 X 50 mL). The organic layers were dried, filtered and concentrated. The crude product was purified by column chromatography, eluting with hexanes/ethyl acetate (4:1) to give N,N-dimethyl-5-nitro-lH-pyrazolo[3,4-b]pyridin-3-amine (0.012 g, 22%) as a solid.

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 1186608-83-2, 3-Bromo-5-nitro-1H-pyrazolo[3,4-b]pyridine.

Reference:
Patent; ARRAY BIOPHARMA INC.; GENENTECH, INC.; AHRENDT, Kateri A.; BUCKMELTER, Alexandre J.; DE MEESE, Jason; GRINA, Jonas; HANSEN, Joshua D.; LAIRD, Ellen R.; LUNGHOFER, Paul; MORENO, David; NEWHOUSE, Brad; REN, Li; SEO, Jeongbeob; TIAN, Hongqi; WENGLOWSKY, Steven Mark; FENG, Bainian; GUNZNER, Janet; MALESKY, Kim; MATHIEU, Simon; RUDOLPH, Joachim; WEN, Zhaoyang; YOUNG, Wendy B.; WO2009/111279; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 60290-21-3, 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.60290-21-3, name is 4-Chloro-1H-pyrrolo[3,2-c]pyridine, molecular formula is C7H5ClN2, molecular weight is 152.581, as common compound, the synthetic route is as follows.

A solution of 4-chloro-1H-pyrrolo[3,2-c]pyridine(100 mg, 0.66 mmol) and 2,4-difluorophenol (213 mg, 1.64 mmol) in DMA (2 mL)was stirred for 5 minutes under nitrogen.Sodium hydride (26.2 mg, 0.66 mmol; 60% in mineral oil) was heated withstirring at 250 C for 3 minutes under microwave irradiation. The mixture was dilutedwith THF (10 mL) and quenched with water and ice (2 mL). The solution wasfiltered through a Varian ChemElute cartridge and concentrated to dryness. The materialwas partially purified by flash chromatography with gradient elution of heptaneand ethyl acetate (1:0 to 0:1) to give a gum. The material was further purifiedby reverse phase preparative HPLC to provide the desired product (49.0 mg, 60.7%) as a solid. HPLC purity: >99% (215nM), >99% (254 nM), >99% (280 nM). 1H NMR (400 MHz, DMSO-d6) d ppm 6.63 (dd, J=3.3, 1.0 Hz, 1 H) 7.08 – 7.19 (m, 2 H) 7.35 – 7.46(m, 3 H) 7.58 (d, J=5.9 Hz, 1 H). HRMS m/z calcd for C13H8F2N2O[M+H]+ 247.0677, found 247.0678.

Statistics shows that 60290-21-3 is playing an increasingly important role. we look forward to future research findings about 4-Chloro-1H-pyrrolo[3,2-c]pyridine.

Reference:
Article; Hu, Yun-Jin; St.-Onge, Miguel; Laliberte, Sebastien; Vallee, Frederic; Jin, Shujuan; Bedard, Leanne; Labrecque, Jean; Albert, Jeffrey S.; Bioorganic and Medicinal Chemistry Letters; vol. 24; 14; (2014); p. 3199 – 3203;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 105250-16-6, 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.105250-16-6, name is (2-Methylpyridin-4-yl)methanol, molecular formula is C7H9NO, molecular weight is 123.15, as common compound, the synthetic route is as follows.

To a stirred, ice-cooled solution of compound 66 (3.68 g, 16.4 mmol), prepared as described in US 6,720,328, in CH2CI2 (50 ml) was added ice-cold TFA (6.07 ml, 9.38 g, 82.1 mmol) via syringe over a period of ~1 min. The resultant clear yellow solution was stirred at 0 0C for 10 min, then at RT for 25h. Volatiles were removed under reduced pressure, and the residue was redissolved in CH2CI2 (35 ml). To this solution was added portionwise (exothermic) 7N methanolic ammonia (5 ml, 35 mmol), making the solution basic to pH paper and resulting in the formation of a precipitate. Solvent was removed under reduced pressure, and the residue was triturated with EtOAc (30 ml). The mixture was filtered, the filtrate was stripped of solvent under reduced pressure, and the residue was purified via flash chromatography on silica gel, eluting with CH2CI2-MeOH -NH3 (90:9:0.25), to obtain compound 67 as an off-white powder (1.43 g; 70percent).

The chemical industry reduces the impact on the environment during synthesis 105250-16-6, I believe this compound will play a more active role in future production and life.

Reference:
Patent; SCHERING CORPORATION; WO2007/1975; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 118289-17-1, 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. 118289-17-1, name is 2-Bromopyridine-4-carboxaldehyde. A new synthetic method of this compound is introduced below.

To a chilled (-780C) solution of 2-bromo-pyridine-4-carbaldehyde (10.0 g, 53.8 mmol) in THF (100 mL) was added a 3 M solution of methylmagnesium chloride in THF (18 mL, 54 mmol) over a 10 minute period. After 1 hour, the yellow solution was allowed to warm gradually to room temperature over a 3 hour period. The reaction was quenched by the slow addition of saturated aqueous NH4Cl (50 mL) and extracted with EtOAc (2 x 200 mL). The combined organic layers were washed with brine, dried over sodium sulfate, and concentrated to afford a brown oil. The crude material was purified by silica gel chromatography eluting with a gradient of 10-45% EtOAc in hexanes to afford l-(2- bromo-pyridin-4-yl)-ethanol.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,118289-17-1, its application will become more common.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; COOK, Brian Nicholas; DISALVO, Darren; FANDRICK, Daniel Robert; HARCKEN, Christian; KUZMICH, Daniel; LEE, Thomas Wai-Ho; LIU, Pingrong; LORD, John; MAO, Can; NEU, Jochen; RAUDENBUSH, Brian Christopher; RAZAVI, Hossein; REEVES, Jonathan Timothy; SONG, Jinhua, J.; SWINAMER, Alan, David; TAN, Zhulin; WO2010/36632; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 871836-51-0 ,Some common heterocyclic compound, 871836-51-0, molecular formula is C6H4ClN3, 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.

Compound 1 (1.00 g, 6.5 mmol) was suspended in acetonitrile (100 ml), and sodium nitrite (339 mg, 8.5 mmol) was added thereto and reacted in an oil bath at 50 ° C. After 1 hour, the reaction mixture was cooled to room temperature, 2-deoxy-3,5-di-O- (p-toluyl) -alpha-D-ribofuranosyl chloride (2.66 g, 6.8 mmol) And the mixture was reacted at room temperature for 30 minutes. After filtration, the filtrate was concentrated under reduced pressure, the solvent was distilled off, the residue was adsorbed on a silica gel column, washed with a mixed solution of ethyl acetate and chloroform Eluting to give compound 2 (1.77 g, 54percent).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,871836-51-0, its application will become more common.

Reference:
Patent; NIHON UNIVERSITY; SAITOU, YOSHIO; SUZUKI, AZUSA; SAITOU, MIO; (41 pag.)JP2016/138078; (2016); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 118289-17-1 ,Some common heterocyclic compound, 118289-17-1, molecular formula is C6H4BrNO, 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: For the synthesis of 3a and 3b, methods ofEmmereich et al. [1] were adapted as follows: Phenylboronic acid, 2-bromopyridine-4/5-carboxyaldehydeand sodium carbonate (2M) were dissolved in a 1:1 mixture of toluene andethanol (v/v, 10ml). The mixture was degassed for 10 minutes and thendichlorobis(triphenylphosphine)palladium(II) was added. The reaction mixturewas heated at 80 C for 5 h under argon atmosphere. The mixture was allowed tocool to room temperature and then organic molecules were extracted intodichloromethane (3×20 ml). Combined extracts were dried over sodium sulphateand then filtered. Upon concentration under reduced pressure crude product wasobtained as dark yellowish green liquid. Chromatography over silica-gel gavethe title compounds (3a and 3b) as liquid or solid. 2-pheny-4-formylpyridine (3a): A mixture of phenylboronic acid (197 mg, 1.6 mmol),2-bromopyridine-4-carboxyaldehyde 2a(200 mg, 1.1 mmol), sodium carbonate (2M, 0.5 ml) and dichlorobis(triphenylphosphine)palladium(II)(37.7 mg, 5%) gave 3a (152 mg,77%) as clear oil. Rf (Etil Asetat:Hekzan, 1:6 v/v) = 0.3. 1H NMR (600 MHz, CDCI3)delta(ppm): 10.14(s, 1H), 8.94 (d, J = 6 Hz, 1H), 8.13 (s, 1H), 8.06 (dd, J = 12Hz and 6 Hz, 2H) , 7.63 (d, J = 6 Hz, 1H), 7.53-7.43 (m,3H). 13C NMR (150 MHz, CDCI3) delta (ppm): 191.6, 159.1,151.1, 142.5, 138.2, 129.7, 128.9, 127.0, 120.5, 118,9.

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. 118289-17-1, 2-Bromopyridine-4-carboxaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Alt?noelcek, Nuray; Aydemir, Murat; Tavasl?, Mustafa; Dos Santos, Paloma L.; Monkman, Andrew P.; Journal of Organometallic Chemistry; vol. 851; (2017); p. 184 – 188;,
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.881-86-7, name is Dimethyl pyridine-2,5-dicarboxylate, molecular formula is C9H9NO4, molecular weight is 195.17, as common compound, the synthetic route is as follows.name: Dimethyl pyridine-2,5-dicarboxylate

To a solution of dimethyl pyridine-2,5-dicarboxylate 59-a (13.0 g, 66.6 mmol) in a mixture of THF (110 mL) and ethanol (110 mL) was added calcium chloride (29.6 g, 266 mmol). After stirring at room temperature for 30 minutes, the reaction was cooled to 0C, and sodium borohydride (3.78 g, 100 mmol) was added portion wise. After the addition was completed the reaction was stirred at room temperature overnight. A saturated aqueous solution of ammonium chloride and dichloromethane were added, the organic layer was separated and the aqueous phase was extracted twice with dichloromethane. The combined organic extracts were washed with brine, dried over MgSO4, filtered and concentrated under reduced pressure to provide Intermediate 59-b as a yellow solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,881-86-7, Dimethyl pyridine-2,5-dicarboxylate, and friends who are interested can also refer to it.

Reference:
Patent; PHARMASCIENCE INC.; LAURENT, Alain; ROSE, Yannick; WO2015/74138; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem