Day: April 14, 2022

Application of 1839-17-4, 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. 1839-17-4, name is N4-Methylpyridine-3,4-diamine. A new synthetic method of this compound is introduced below.

Example 121C1 ,2-Dimethyl- lH-imidazo[4,5-c]pyridine[00747] The solution of N4-methylpyridine-3,4-diamine (2.5 g, 20.3 mmol) in acetic anhydride (25 mL) was refluxed overnight. Then acetic anhydride was evaporated under reduced pressure and 1 N hydrochloride acid was added. Then the mixture was extracted with dichloromethane (50 mL x 3). The aqueous layer was neutralized with sodium bicarbonate, and extracted with dichloromethane (50 mL x 3). The organic layers were concentrated to give the title compound (1.9 g, yield 64%). LC-MS (ESI) m/z: 148 (M+l)+. ^-NMR (400 MHz, CDC13) delta (ppm): 2.64 (s, 3H), 3.74 (s, 3H), 7.23-7.24 (d, J= 5.2 Hz, 1H), 8.39-8.41 (d, J= 5.2 Hz, 1H), 8.98 (s, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1839-17-4, N4-Methylpyridine-3,4-diamine, and friends who are interested can also refer to it.

Reference:
Patent; BIOMARIN PHARMACEUTICAL INC.; WANG, Bing; CHU, Daniel; WO2011/130661; (2011); 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. 823221-93-8, name is 5-Bromo-2-chloro-4-(trifluoromethyl)pyridine. This compound has unique chemical properties. The synthetic route is as follows. Application In Synthesis of 5-Bromo-2-chloro-4-(trifluoromethyl)pyridine

A stirred solution of 20% n-butyl magnesium chloride (63 mL, 127.2 mmol, 1.1 eq) in THF (50 mL) was cooled to 0 C and n-butyl lithium (48 mL, 115.8 mmol, le q, 2.5M in hexane) was added. The resulting reaction mixture was stirred for 10 mm, then diluted with THF (100 mL), cooled to -78 C and a solution of 5-bromo-2-chloro-4-(trifluoromethyl)pyridine (30 g, 115.8 mmol, 1 eq) in THF (50 mL) was added. The reaction mixture was stirred for lh at -78 C. The mixture was quenched with crushed dry ice and allowed to warm to RT and stirred for 16 h. TLC analysis indicated the formation of a polar spot. The reaction mixture was concentrated, acidified with 2N HC1 (80 mL) and extracted with EtOAc (2 x 500 mL). The combined organic layers were dried over Na2SO4 and concentrated under reduced pressure to give the crude compound which was recrystallized from n-pentane (30 mL) and dried on high vacuum to give 6-chloro-4-(trifluoromethyl)nicotinic acid (14 g, 53.8% yield) as off white solid. LCMS: [M+Hj 226.29.

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, 823221-93-8, 5-Bromo-2-chloro-4-(trifluoromethyl)pyridine.

Reference:
Patent; PROPELLON THERAPEUTICS INC.; AL-AWAR, Rima; ISAAC, Methvin; JOSEPH, Babu; LIU, Yong; MAMAI, Ahmed; PODA, Gennady; SUBRAMANIAN, Pandiaraju; UEHLING, David; WILSON, Brian; ZEPEDA-VELAZQUEZ, Carlos Armando; (311 pag.)WO2019/46944; (2019); 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. 849067-97-6, name is (1H-Pyrrolo[2,3-b]pyridin-5-yl)methanol, the common compound, a new synthetic route is introduced below. name: (1H-Pyrrolo[2,3-b]pyridin-5-yl)methanol

B. lH-Pyrrolo[2,3-b]pyridine-5-carbaldehyde.; (1H-Pyrrolo[2,3- b]pyridin-5-yl)methanol (crude from previous reaction) was dissolved in anhydrous methylenechloride (50 mL). Pyridiniumchlorochromate (3.70 g, 17.0 mmol) was added to the solution and stirred at room temperature overnight. The reaction mixture was filtered through silica gel and washed with ethyl acetate. Organics were poured into water (150 mL), extracted with EtOAc (4×100 mL), combined organic layers were dried with sodium sulfate, and concentrated under reduced pressure to afford the title compound (0.72 g, 4.93 mmol, 87percent over 2 steps) as a white solid. MS (ESI) m/z 147.1 [M+ 1]+.

The synthetic route of 849067-97-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SIGNAL PHARMACEUTICALS, LLC; WO2008/51494; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 69045-83-6 ,Some common heterocyclic compound, 69045-83-6, molecular formula is C6H2Cl5N, 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.

Take intermediate 2,3-dichloro-5-trichloromethylpyridine 50g,After adding the catalyst, the temperature is raised to 170C.Slowly introduce anhydrous hydrogen fluoride gas,Reaction 11h, after the end of the reaction, neutralized with 5% sodium bicarbonate solution,Separate the organic phase, washed,The crude product obtained after drying was 2,3-dichloro-5-trifluoromethylpyridine as the desired material in an amount of 85% and the yield was 65%.

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. 69045-83-6, 2,3-Dichloro-5-(trichloromethyl)pyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Shandong Eastern Countries Nong Pharmaceutical Ji Industrial Co., Ltd.; Yu Lexiang; Li Yuan; Liu Weihua; Sun Meixin; Sun Fujiang; (7 pag.)CN106748985; (2017); A;,
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. 139585-48-1, name is 2-Chloro-5-methoxypyridine. This compound has unique chemical properties. The synthetic route is as follows. Quality Control of 2-Chloro-5-methoxypyridine

a) 5′-Methoxy-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-carboxylic acid ethyl ester To a stirred solution of piperidine-4-carboxylic acid ethyl ester (0.52 g, 3.34 mmol) and 2-chloro-5-methoxy-pyridine in 10 mL of toluene was added (13 mg, 0.057 mmol) of Pd(II) acetate, (17 mg, 0.027 mmol) of BINAP and tBuOK (0.44 g, 3.90 mmol). The mixture was heated at 120 C. for two hours, concentrated under vacuo and the residue was directly purified on column chromatography (SiO2, EtOAc/Hept 1:2) yielding 0.17 g (24%) of the title compound as a light yellow oil. ES-MS m/e: 265.3 (M-41′).

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; Jablonski, Philippe; Knust, Henner; Nettekoven, Matthias; Patiny-Adam, Angelique; Ratni, Hasane; Riemer, Claus; US2011/53948; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 72093-04-0, 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. 72093-04-0, name is 3-Chloro-4-methylpyridine, molecular formula is C6H6ClN, 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.

To a solution of lithium diisopropylamide (30mL, 2M in THF) at -70C is added under argon a solutionof 3-chloro-4-methylpyridine (6.3 8g. 1 eq, 50mmol) in 25ml THF. The mixture is stirred for 5min at -70C and then allowed to reach -30C. Thereafter the mixture is cooled dowxi to -70C and a solution of 2- chloro- 1-( 1 -chlorocyclopropyl)ethanone (9.1 8g, 1 .2eq, 6Ommol) in 25mL THF is added. Then the mixture is allowed to reach ambient temperature and stirred for lh. Thereafter the mixture is cooled to 0C and saturated aqueous ammonium chloride solution is added. After extraction with ethyl acetate andevaporation of the solvent the crude material is purified via column chromatography over silica gel (eluent cyclohexane / ethyl acetate gradient). After evaporation of the solvent lOg (73%) of 3 -chloro-4- { [2-( 1- chlorocyclopropyl)oxiran-2-ylmethyl}pyridine are obtained as colowless oil.

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 72093-04-0, 3-Chloro-4-methylpyridine.

Reference:
Patent; BAYER CROPSCIENCE AG; SUDAU, Alexander; HOFFMANN, Sebastian; DAHMEN, Peter; WACHENDORFF-NEUMANN, Ulrike; BERNIER, David; LACHAISE, Helene; BRUNET, Stephane; VIDAL, Jacky; GENIX, Pierre; COQUERON, Pierre-Yves; GEIST, Julie; VORS, Jean-Pierre; KENNEL, Philippe; MILLER, Ricarda; WO2014/167009; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 84199-61-1 ,Some common heterocyclic compound, 84199-61-1, molecular formula is C7H6BrNO, 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.

Synthesis of 7-(3,4,5-trimethoxyphenyl)quinolin-5-ol (6.2) for Examples 2, 3, 4, 5, 9, 18, 23[0276] 3-Acetyl-2-bromopyridine, 140 mg 5-ethynyl-1,2,3-trimethoxybenzene 2.1, 101 muL triethylamine, 17 mg triphenylphosphinpalladium(II) chlorid, 1 mg Cu(I)I were suspended in 4 mL THF under argon atmosphere and stirred for 1 h at 25 C. The mixture was diluted with DCM and extracted with diluted aq. NH3 and saturated NH4Cl solution. The organic phase was concentrated and the mixture separated via FCC (10 g SiO2, Cyclohexane?cyclohexane/ethylacetate 70:30) to yield 90 mg 1-(2-(3,4,5-trimethoxyphenylethynyl)pyridin-3-yl)ethanone as solid. Analysis: HPLC-MS: Rt=1.21 min (method E) M+H=312.

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. 84199-61-1, 3-Acetyl-2-bromopyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; HOFFMANN, Matthias; BISCHOFF, Daniel; DAHMANN, Georg; KLICIC, Jasna; SCHAENZLE, Gerhard; WOLLIN, Stefan Ludwig Michael; CONVERS-REIGNIER, Serge Gaston; EAST, Stephen Peter; MARLIN, Frederic Jacques; McCARTHY, Clive; SCOTT, John; US2013/29949; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1003711-43-0, 2-Bromo-5-hydroxy-3-methylpyridine, 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, Computed Properties of C6H6BrNO, blongs to pyridine-derivatives compound. Computed Properties of C6H6BrNO

(A) A mixture of 6-bromo-5-methylpyridin-3-ol (1 g, 5.32 mmol), 1-bromo-2-methoxyethane (730 mg, 5.25 mmol) and K2CO3 (1.5 g, 10.87 mmol) in MeCN (20 mL) was stirred at rt overnight, after which the reaction was quenched by the addition of water (100 mL). The resulting solution was extracted with EtOAc (2*100 mL) and the combined organic phase was dried (Na2SO4) and concentrated under reduced pressure. The resultant residue was purified by silica gel chromatography (0-15% EtOAc/petroleum ether) to afford 2-bromo-5-(2-methoxyethoxy)-3-methylpyridine (500 mg, 38%) as colorless oil. LC/MS: mass calcd. for C9H12BrNO2: 246.10, found: 246.0 [M]+, 248.0 [M+2]+.

The synthetic route of 1003711-43-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Janssen Pharmaceutica NV; Liang, Yin; Demarest, Keith T.; (109 pag.)US2017/290800; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 22282-96-8, 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. 22282-96-8, name is 2-Bromo-6-methyl-5-nitropyridine, molecular formula is C6H5BrN2O2, 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 suspension of 6-bromo-2-methyl-3-nitropyridine (XIV) (250 g, 1.15 mol, 1.00 eq) and NH4C1 (300 g, 5.61 mol, 4.88 eq) in EtOH (3.50 L) and water (150 mL) was heated with stirring to 65C. To this mixture was added Fe (130 g, 2.33 mol, 2.02 eq) and HC1 (15.3 g, 419 mmol, 0.36 eq). The suspension was then heated to 80C for another 3 h. The reaction was cooled to 25C and filtered through a plug of Celite. The filtrate was concentrated under reduced pressure to yield a residue that was taken up in EtOAc (1 L x 3) and washed with brine. The organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure to give 6-bromo-2-methylpyridin-3-amine (XV) as brown solid (373 g, 1.99 mol, 86.7% yield) which was used for the next step without any purification. l NMR (DMSO- tf, 400 MHz) delta ppm 6.01 (dd, J = 2.3, 7.9 Hz, 2H), 7.03 (d, J = 8.2 Hz, 1H); ESIMS found for C6H7BrN2 mlz 186.8 (M+H).

According to the analysis of related databases, 22282-96-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SAMUMED, LLC.; KC, Sunil Kumar; WALLACE, David Mark; CAO, Jianguo; CHIRUTA, Chandramouli; HOOD, John; (247 pag.)WO2017/24004; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1083057-12-8, 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 1083057-12-8, name is tert-Butyl 3-(3-methylpyridin-2-yl)benzoate. This compound has unique chemical properties. The synthetic route is as follows.

tert-Butyl-3-(3-methylpyridin-2-yl)benzoate (1.0 eq) is dissolved in EtOAc (6 vol). Water (0. 3 vol) is added followed by urea-hydrogen peroxide (3 eq). The phthalic anhydride (3 eq) is added portion-wise as a solid to maintain the temperature in the reactor below 45 0C. After completion of phthalic anhydride addition, the mixture is heated to 45 0C. After stirring for an additional 4 hours, the heat is turned off. 10% w/w aqueous Na2SO3 (1.5 eq) is added via addition funnel. After completion of Na2SO3 addition, the mixture is stirred for an additional 30 minutes and the layers separated. The organic layer is stirred and 10% w/w aq. Na2Ctheta3 (2 eq) is added. After stirring for 30 minutes, the layers are allowed to separate. The organic phase is washed 13% w/v aq NaCl. The organic phase is then filtered and concentrated to afford crude 2-(3-(tert-butoxycarbonyl)phenyl)-3-methylpyridine-l -oxide (95%) that is used directly in the next step.

According to the analysis of related databases, 1083057-12-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; WO2009/73757; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem