Month: April 2022

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. 1201676-03-0, name is 4,6-Dichloro-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-1-one, molecular formula is C7H4Cl2N2O, 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 4,6-Dichloro-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-1-one

4,6-Dichloro-2,3-dihydro-pyrrolo[3,4-c]pyridin-1-one (5.63 g, 27.7 mmol), te/f-butyl piperazine-1-carboxylate (7.75 g, 41.6 mmol), triethylamine (14.Og, 139 mmol), and dioxane (50 ml.) are stirred at 120 0C in a 350 ml. sealed tube for 16 h. To the cooled down reaction mixture are then added more te/f-butyl piperazine-1-carboxylate (5.2 g, 27.7 mmol) and triethylamine (2.83 g, 28.0 mmol). The vessel is sealed again and stirred at 120 0C for 24 h. The reaction mixture is then cooled to ambient temperature, and a light-pink solid is isolated by filtration (6.18 g, 17.5 mmol, 63%). MS(ESI) m/z 353.15 (M+1 ). 1H NMR (400 MHz, DMSOd6) delta ppm 9.04 (s, 1 H), 6.89 (s, 1 H), 4.57 (s, 2 H), 3.61 – 3.54 (m, 4 H), 3.47 – 3.41 (m, 4 H), 1.42 (s, 9 H).D. 4-(4-Chloro-1 -oxo-2,3-dihydro-1 H-pyrrolo[3,4-c]pyridin-6-yl)-piperazine-1 -carboxylic acid terf-butyl ester. The title compound is typically obtained from the dioxane filtrate after isolation of 4- (6-chloro-1 -oxo-2,3-dihydro-1 /-/-pyrrolo[3,4-c]pyridin-4-yl)-piperazine-1 -carboxylic acid tert- butyl ester. The dioxane is removed by rotary evaporation. Treatment with methanol yields a light yellow solid which is isolated by filtration. MS(ESI) m/z 353.30 (M+1 ). 1H NMR (400 MHz, DMSOd6) delta ppm 8.93 (s, 1 H), 7.01 (s, 1 H), 4.28 (s, 2 H), 3.58 – 3.53 (m, 4 H), 3.45 – 3.40 (m, 4 H), 1.42 (S, 9 H).

With the rapid development of chemical substances, we look forward to future research findings about 1201676-03-0.

Reference:
Patent; NOVARTIS AG; WO2009/150230; (2009); 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. 886365-00-0, name is 2,5-Dichloro-4-methylpyridine. This compound has unique chemical properties. The synthetic route is as follows. Formula: C6H5Cl2N

2,5-Dichloro-4-methylpyridine (7 g, 43.2 mmol), 2-methyl-8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzofuro[2,3-b]pyridine (13.36 g, 43.2 mmol), and potassium carbonate (11.94 g, 86 mmol) were suspended in a mixture of DME (180 ml) and water (10 ml) under nitrogen at room temperature. Tetrakis(triphenylphosphine)palladium(0) (Pd(PPh3)4) (0.499 g, 0.432 mmol) was added as one portion, the reaction mixture was degassed and heated at 100 C. for 14 hours under nitrogen. The reaction mixture was then cooled down to room temperature and the organic phase was separated and filtered. Ethanol (100 ml) was added as one portion and the resulting mixture was stirred, then the white precipitate was filtered off. The remaining solution was evaporated and the residue was subjected to column chromatography on silica gel column, eluted with heptanes/DCM 1/1 (v/v), then heptanes/EtOAc 4/1 (v/v) to yield a white solid, which was combined with the white precipitate. The combined solids were recrystallized from DCM/heptanes, yielding 8-(5-chloro-4-methylpyridin-2-yl)-2-methylbenzofuro[2,3-b]pyridine (11 g, 83% 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, 886365-00-0, 2,5-Dichloro-4-methylpyridine.

Reference:
Patent; Universal Display Corporation; TSAI, Jui-Yi; DYATKIN, Alexey Borisovich; YEAGER, Walter; XIA, Chuanjun; (238 pag.)US2018/102487; (2018); 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. 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. Product Details of 1083057-12-8

Preparation of 2-(3-(tert-butoxycarbonyl)phenyl)-3-methylpyridine-1-oxide tert-Butyl-3-(3-methylpyridin-2-yl)benzoate (1.0 eq) was dissolved in EtOAc (6 vol). Water (0.3 vol) was added, followed by urea-hydrogen peroxide (3 eq). Phthalic anhydride (3 eq) was then added portionwise to the mixture as a solid at a rate to maintain the temperature in the reactor below 45 C. After completion of the phthalic anhydride addition, the mixture was heated to 45 C. After stirring for an additional 4 hours, the heat was turned off. 10% w/w aqueous Na2SO3 (1.5 eq) was added via addition funnel. After completion of Na2SO3 addition, the mixture was stirred for an additional 30 min and the layers separated. The organic layer was stirred and 10% wt/wt aqueous. Na2CO3 (2 eq) was added. After stirring for 30 minutes, the layers were allowed to separate. The organic phase was washed 13% w/v aq NaCl. The organic phase was then filtered and concentrated to afford crude 2-(3-(tert-butoxycarbonyl)phenyl)-3-methylpyridine-1-oxide (95%) that was used directly in the next step.

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, 1083057-12-8, tert-Butyl 3-(3-methylpyridin-2-yl)benzoate.

Reference:
Patent; Vertex Pharmaceuticals Incorporated; Verwijs, Marinus Jacoubus; US2013/186801; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 185017-72-5, 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 185017-72-5, name is 3-Bromo-2-chloro-6-picoline. This compound has unique chemical properties. The synthetic route is as follows.

(5-Bromo-6-methoxy-pyridin-2-yl)-methanol (356a) step a-To a solution of 3-bromo-2-chloro-6-methyl-pyridine (2.0 g, 0.687 mmol) in CHCl3 was added MCPBA (3.3 g, 19.1 mmol) and the resulting solution was heated at 50 C. overnight. The resulted solution was cooled and partitioned between DCM and sat’d. aq. NaHCO3. The organic layer was dried (Na2SO4), filtered and concentrated in vacuo. The crude product was purified by SiO2 chromatography eluding with an EtOAc/hexane gradient (30 to 80% EtOAc) to afford 1.88 g (87%) of 3-bromo-2-chloro-6-methyl-pyridine 1-oxide (357a) as a white solid. step b-A solution of 357a (0.5 g) and 0.5 M NaOMe/MeOH (4.9 mL) was stirred at RT overnight. The reaction mixture was concentrated in vacuo and the residue loaded on a SiO2 column and eluted with 5% MeOH/DCM to afford 3-bromo-2-methoxy-6-methyl-pyridine 1-oxide (357b).

According to the analysis of related databases, 185017-72-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Roche Palo Alto LLC; US2010/21423; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 65873-72-5, 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 65873-72-5, name is 6-Methoxynicotinaldehyde. This compound has unique chemical properties. The synthetic route is as follows.

Intermediate 150: 6-Hydroxypyridine-3-carbaldehydeTo A 100 mL RB was charged with 6-methoxypyridine-3-carbaldehyde (1 g, 7 mmol) was added 3N HCI (20 mL) and then refluxed it at 100 C for 12h. RM was cooled slowly to RT. Solid was obtained up on cooling. It was filtered off on Buchner flask and dried under line vacuum to obtain the title compound as white crystals (0.3g, Yield: 37%)

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 65873-72-5, 6-Methoxynicotinaldehyde.

Reference:
Patent; CONNEXIOS LIFE SCIENCES PVT. LTD.; RANGANATH RAO, Jagannath Madanahalli; ARUMUGAM, Nagarajan; ANSARI, Mohd Mudabbir; GUDLA, Chandrasekhar; PACHIYAPPAN, Shanmugam; RAMALINGAM, Manivannan; GEORGE, Jenson; ARUL, George Fernanda; BOMMEGOWDA, Y, Kenchegowda; ANGUPILLAI, Sathesh Kumar; KOTTAMALAI, Ramamoorthy; JIDUGU, Pradeep; RAO, D, Shivanageshwara; WO2012/11125; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route 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.

30 mol of the compound 3-chloro-4-methylpyridine was dissolved in an aqueous solution containing 1.2 times the molar amount of methylamine, and then 0.2 mol of cuprous chloride was added thereto, and then heated to 140-150 degrees, and the raw material disappeared. The heating was stopped, cooled to room temperature, and the reaction liquid was extracted with dichloromethane, and then the organic phase was concentrated to give product 4, and the reaction yield was 65%.

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; Gansu Haotian Pharmaceutical Co., Ltd.; Xue Jijun; Yang Bo; Li Xuehai; Wang Shijiao; Qi Tafamingrenqingqiubugongkaixingming; (12 pag.)CN108689915; (2018); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 443956-08-9, 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. 443956-08-9, name is 6-Bromo-2-nitropyridin-3-ol. A new synthetic method of this compound is introduced below.

To a stirred solution of 6-bromo-2-nitropyridin-3-ol (6 g, 27.40 mmol) in EtOH (100 mL) was added iron (11.00 g, 197.00 mmol), calcium chloride (3.04 g, 27.4 mmol) and the reaction mixture for was heated at 85 C for 16 h. The reaction mixture was cooled to ambient temperature, filtered through celite and the filtrate was evaporated under reduced pressure. The residue was purified by column chromatography (Redisep-80 g, 10-20% MeOH/DCM) to obtain Intermediate 115A (3.00 g, 57.90%) as a yellow solid.1H NMR (400 MHz, DMSO-d6) delta ppm 6.50 (d, J = 7.78 Hz, 1 H), 6.75 (d, J = 7.78 Hz, 1 H), 9.70 (br. s, 1 H). (2 Exchangeable proton not observed). LCMS (Method-O): retention time 0.64 min, [M+2H] 191.3.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,443956-08-9, 6-Bromo-2-nitropyridin-3-ol, and friends who are interested can also refer to it.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; GUNAGA, Prashantha; BHIDE, Rajeev S.; BORA, Rajesh Onkardas; PANDA, Manoranjan; YADAV, Navnath Dnyanoba; PRIESTLEY, Eldon Scott; RICHTER, Jeremy; (321 pag.)WO2018/93569; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 951625-93-7, 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.951625-93-7, name is Methyl 4-chloro-1H-pyrrolo[2,3-b]pyridine-5-carboxylate, molecular formula is C9H7ClN2O2, molecular weight is 210.62, as common compound, the synthetic route is as follows.

[0168] To a solution of methyl 4-chloro-lH-pyrrolo[2,3-b]pyridine-5-carboxylate (2.3 g, 11 mmol) in dimethylformamide (DMF; 20 mL) was added NaH (0.67 g, 17 mmol, 60% purity) under nitrogen. The mixture was stirred at 0 C for 0.5 hours. To this was added chloromethyl methyl ether (1.1 g, 13 mmol, 1 mL) and the reaction was stirred at 25 C for 2 hours. Upon completion, the reaction mixture was quenched by addition aqueous saturated NH4C1 solution (20 mL) and diluted with water (10 mL). The mixture was extracted with ethyl acetate (3x 40 mL). Organic layers were combined, washed with brine (2x 25 mL), dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography to give methyl 4-chloro-l-(methoxymethyl)-lH-pyrrolo[2,3-b]pyridine-5- carboxylate (2.3 g, 8.6 mmol, 78% yield) as a yellow solid.

Statistics shows that 951625-93-7 is playing an increasingly important role. we look forward to future research findings about Methyl 4-chloro-1H-pyrrolo[2,3-b]pyridine-5-carboxylate.

Reference:
Patent; SYROS PHARMACEUTICALS, INC.; ZHANG, Yi; AUSTGEN, Kathryn; CHUAQUI, Claudio Edmundo; MALOJCIC, Goran; SINKO, William; GUAN, Huiping Amy; SAVOIE, Tracey Lodie; (92 pag.)WO2018/191587; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 824-51-1, 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. 824-51-1, name is 6-Methyl-1H-pyrrolo[2,3-b]pyridine. A new synthetic method of this compound is introduced below.

A solution of 6-methyl-1 H-pyrrolo[2,3-b]pyridine (1.07g, 8.1 mmol) in ethyl acetate (37ml_) at 0C was treated with mCPBA (2.1 g, 12.2mmol) then stirred at 0C for 40 mins. mCPBA (0.21g, 1.2mmol) was added at 0C then left to warm to r.t and stirred overnight. Saturated aqueous sodium bicarbonate was added and the organic layer was separated. The aqueous was extracted with ethyl acetate, the combined organic phase was washed with saturated sodium bicarbonate, brine then dried (Na2S04) and concentrated in vacuo. The aqueous layers were combined and extracted with 2-methyltetrahydrofuran and the combined extracts were dried (Na2S04) and concentrated in vacuo. The two crude products were dissolved in hot methanol, combined, preadsorbed onto diatomaceous earth and purified by FCC eluting with 0-10% MeOH / DCM to afford the title compound as a pale orange solid (0.57g, 48%) LCMS (Method 3): Rt 0.74 min, m/z 149.1 [MH+].

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,824-51-1, its application will become more common.

Reference:
Patent; THE UNIVERSITY OF NOTTINGHAM; BROOK, David; HAYES, Chris; BENNETT, Nicholas; PALFRAMAN, Matthew; CRAMP, Sue; BULL, Richard; BODNARCHUK, Michael; (262 pag.)WO2019/58132; (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. 72141-44-7, name is 4-Chloro-2-methoxypyridine, the common compound, a new synthetic route is introduced below. category: pyridine-derivatives

(e) 10.0 g (69.9 mmol) of the crude product of 4-chloro-2-methoxypyridine obtained in step (d) was dissolved in 100 mL of dimethylformamide, and 37.2 g (279 mmol) of N-chlorosuccinimide was added, followed by stirring at room temperature for 12 hours. 400 mL of water was added to terminate the reaction. Extraction with ethyl ether was carried out, then the organic layer was washed with a saturated sodium chloride aqueous solution, dried over sodium sulfate and subjected to filtration, and the solvent was distilled off under reduced pressure to obtain 9.10 g (crude yield 73%) of a crude product of 4,5-dichloro-2-methoxypyridine.1H-NMR(CDCl3, 400 MHz) : delta (ppm) = 3.90(s, 3H), 6.85(s, 1H), 8.14(s, 1H)

The synthetic route of 72141-44-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ISHIHARA SANGYO KAISHA, LTD.; EP1559320; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem