Day: April 19, 2022

Electric Literature of 24195-07-1, 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. 24195-07-1, name is 2-(Methoxycarbonyl)nicotinic acid. A new synthetic method of this compound is introduced below.

2-(Methoxycarbonyl)pyridine-3-carboxylic acid (3 g, 16.57 mmol) was dissolved in 50 mL of t-ButOH and 4 mL of TEA were added. The solution was stirred for 5 min at room temperature, then diphenylphosphorylazide (3.6 mL, 16.57 mmol) was added and the reaction was refluxed for 3 hours. The mixture was concentrated and the residue purified flash chromatography (silica) eluting with ethyl acetate in cyclohexane from 20 to 50%. The fractions containing the product were collected and concentrated in vacuo to give methyl 3-{[(tert- butoxy)carbonyl]amino}pyridine-2-carboxylate (1.6 g, 38.5% yield).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,24195-07-1, 2-(Methoxycarbonyl)nicotinic acid, and friends who are interested can also refer to it.

Reference:
Patent; PHARMACYCLICS LLC.; ATALLAH, Gordana, Babic; CHEN, Wei; JIA, Zhaozhong, J.; POZZAN, Alfonso; RAVEGLIA, Lucal, Francesco; ZANALETTI, Riccardo; (815 pag.)WO2016/196776; (2016); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 473927-69-4, 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.473927-69-4, name is 1-(4-Iodophenyl)-3-morpholino-5,6-dihydropyridin-2(1H)-one, molecular formula is C15H17IN2O2, molecular weight is 384.21, as common compound, the synthetic route is as follows.

Tetramethylethylenediamine (TMEDA, 27.2 mL) was dissolved in THF300 mL) in an inert atmosphere, then cooled to -78C before the drop-wise addition ofn-BuLi (67.6 mL, 2.5 M). 2-bromo-1,3-thiazole (15.2 mL) was added drop-wise and agitation was continued 30 minutes at -78C. Compound 1E (25 g, 139.50 mmol, 1.00 equiv) dissolved in THF (100 mL) was added drop-wise. Agitation was continued for 30 minutes at -78C then 2 hours at -10C. The reaction was neutralised with 500 mLof KHSO4 (sat.), then extracted 3 times with 1 litre of EtOAc. The organic phases were combined, washed twice with 400 mL water and twice with 700 mL of NaC1 (sat.), then dried over sodium sulfate, filtered and concentrated. The residue was purified on a silica column with a mixture of EtOAc and PE (1:100 to 1:10) to yield 25 g (88 %) of compound iF in the form of a yellow oil.

The chemical industry reduces the impact on the environment during synthesis 473927-69-4, I believe this compound will play a more active role in future production and life.

Reference:
Patent; PIERRE FABRE MEDICAMENT; PEREZ, Michel; RILATT, Ian; LAMOTHE, Marie; WO2014/174060; (2014); 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. 42959-38-6, name is 2-Chloro-5-nitronicotinic acid, the common compound, a new synthetic route is introduced below. Computed Properties of C6H3ClN2O4

To 2-chloro-5-nitronicotinic acid (1.0 mmol) in methanol was added a solution of sodium methoxide in methanol (2.4 mmol, freshly prepared from sodium metal in methanol). The solution was refluxed for 2 h and the mixture was allowed to cool and concentrated in vacuo. To the resulting residue was added 10% citric acid solution (20 ml) and the solution extracted with ethyl acetate (20 ml). The organic layer was dried (MgS04) and concentrated in vacuo. The residue was crystallised from water to give a yellow-white solid (73%). (0184) ESIMS: M-l 197. (0185) 1H NMR (300 MHz, DMSO) d 9.30 (1H, d, H-4), 8.83 (1H, d, H-6), 4.05 (3H, s, OCH3).

The synthetic route of 42959-38-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BIONOMICS LIMITED; O’CONNOR, Sue; RATHJEN, Deborah; (55 pag.)WO2019/109150; (2019); 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.4282-47-7, name is 2-(4-Nitrophenyl)pyridine, molecular formula is C11H8N2O2, molecular weight is 200.1934, as common compound, the synthetic route is as follows.Recommanded Product: 2-(4-Nitrophenyl)pyridine

2-(4-Nitrophenyl)pyridine (1.10 g) and 10% Pd/C (300 mg) were dissolved suspended in 80 mL of an 8:1 solution of 30 mL of THF and 10 mL of ethanol under an atmosphere of dry N2. To this solution was added 1.0 mL of anhydrous hydrazine. The reaction mixture was stirred at room temperature overnight and then filtered. The filtrate was concentrated under vacuum. The residue was partitioned between dichloromethane and water and the organic layer was washed with brine, dried over MgSO4, filtered and concentrated under vacuum. The residue was purified via silica gel chromatography to give 653.3 mg of 4-(pyridin- 2-yl)benzenamine.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,4282-47-7, 2-(4-Nitrophenyl)pyridine, and friends who are interested can also refer to it.

Reference:
Patent; ARRAY BIOPHARMA, INC.; WO2007/130743; (2007); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 131747-62-1, 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. 131747-62-1, name is 3-(Trifluoromethyl)pyridine-2-carboxaldehyde, molecular formula is C7H4F3NO, 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 214 (110 mg, 0.322 mmol)) in toluene 15 ml was added 66 (84.9 mg, 0.483 mmol). PTSA (122.4 mg, 0.644 mmol) was added to the reaction mass, which was stirred at 120 C. for 6 h. The reaction mass was diluted with ethyl acetate and washed with water (3×25 mL). The organic layer was dried over sodium sulphate and concentrated to get the crude 215, which was purified through flash chromatography by using 100-200 mesh silica gel. The compound was eluted at 10% ethyl acetate in hexane to afford yellow coloured solid 215.

According to the analysis of related databases, 131747-62-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Vankayalapati, Hariprasad; Yerramreddy, Venkatakrishnareddy; US2015/72980; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 92992-85-3, 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. 92992-85-3, name is 2-Bromo-3,5-dimethylpyridine. A new synthetic method of this compound is introduced below.

To (2S,4S)-4-amino-2-methoxymethylpyrrolidine-1-carboxylic acid tert-butyl ester (300 mg) were added 2-bromo-3,5-dimethylpyridine (291 mg),tris(dibenzylideneacetone)dipalladium(O)(30 mg),2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (41 mg),sodium tert-butoxide (188 mg) and toluene (6 mL) and the mixture was stirred at 80c for 6 hr. The reaction mixture was purified by column chromatography (hexane:ethyl acetate)to give (2S,4S)-4-(3,5-dimethylpyridin-2-ylarnino)-2-methoxymethylpyrrolidine-1-carboxylic acid tert-butyl ester (489 mg).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,92992-85-3, its application will become more common.

Reference:
Patent; Mitsubishi Tanabe Pharma Corporation; ISHIBUCHI, Seigo; SARUTA, Kunio; HAMADA, Maiko; MATOBA, Nobuatsu; MATSUDAIRA, Tetsuji; SEKI, Maki; TARAO, Akiko; HONJO, Takashi; OGATA, Shingo; KAWATA, Atsushi; MOROKUMA, Kenji; FUJIE, Naoto; AOYAMA, Yukio; (251 pag.)EP3321256; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1111637-74-1, 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. 1111637-74-1, name is 1-(5-Bromo-2-fluoropyridin-3-yl)ethanone, molecular formula is C7H5BrFNO, 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 mixture of 1 -(5-bromo-2-fluoropyridin-3- yl)ethanone (prepared according to procedures described in WO2009016460; 11.0 g, 50.5 mmol), (R)-2-methylpropane-2-sulfinamide (AK Scientific, 12.2 g, 101.0 mmol) and titanium(IV) ethoxide (Aldrich, 26.1 mL, 126.0 mmol) in THF (100 mL) was heated to reflux for 2 h. The mixture was cooled to room temperature, and brine (200 mL) was added. The suspension was vigorously stirred for 10 min. The suspension was filtered through a pad of silica gel and the organic phase was separated. The aqueous phase was extracted with EtOAc. The combined organic layers were washed with brine, dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by silica gel chromatography (gradient 0-20% EtOAc/hexanes) to afford (R,Z)-N-(1 -(5-bromo-2- fluoropyridin-3-yl)ethylidene)-2-methylpropane-2-sulfinamide (214A) as a bright yellow oil (16 g, 49.8 mmol, 99% yield). MS m/z= 320.8 [M+H]+.

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 1111637-74-1, 1-(5-Bromo-2-fluoropyridin-3-yl)ethanone.

Reference:
Patent; AMGEN INC.; ALLEN, Jennifer R.; AMEGADZIE, Albert; BOURBEAU, Matthew P.; BROWN, James A.; CHEN, Jian J.; CHENG, Yuan; FROHN, Michael J.; GUZMAN-PEREZ, Angel; HARRINGTON, Paul E.; LIU, Longbin; LIU, Qingyian; LOW, Jonathan D.; MA, Vu Van; MANNING, James; MINATTI, Ana Elena; NGUYEN, Thomas T.; NISHMURA, Nobuko; NORMAN, Mark H.; PETTUS, Liping H.; PICKRELL, Alexander J.; QIAN, Wenyuan; RUMFELT, Shannon; RZASA, Robert M.; SIEGMUND, Aaron C.; STEC, Markian M.; WHITE, Ryan; XUE, Qiufen; (759 pag.)WO2016/22724; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 72093-13-1, 6-Chloro-2,3-dimethylpyridine, 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, 72093-13-1, blongs to pyridine-derivatives compound. Recommanded Product: 6-Chloro-2,3-dimethylpyridine

A mixture of 6-chloro-2,3-dimethylpyridine (400 mg), N-(czs-4-aminocyclohexyl)-3-chloro- 4-fluorobenzamide obtained in step A of example 1 (841 mg), and BuOH (0.8 mL) was heated in a microwave synthesizer at 180 0C for 20 min and 230 0C for 50 min. The mixture was diluted with CHCl3 and added to aqueous saturated NaHCO3. The aqueous layer was extracted with CHCl3 three times. The combined organic layer was dried over MgSO4, filtrated, concentrated under reduced pressure, and purified by medium-pressure liquid chromatography (NH-silica gel, 20% to 99% EtOAc EPO in hexane and silica gel, 3% to 5% MeOH in CHCl3) to give 3-chloro-N-{c/s-4-[(5,6- dimethylpyridin-2-yl)amino]cyclohexyl}-4-fluorobenzamide. To a solution of the above material in EtOAG (3 mL) was added 4 M hydrogen chloride in EtOAc (0.18 mL). The mixture was stirred at ambient temperature for 4 h and concentrated under reduced pressure. The residue was suspended in Et2O and the suspension was stirred at ambient temperature. The precipitate was collected by filtration, washed with Et2O, and dried at 80 0C under reduced pressure to give 3-chloro-N-{c-4- [(5,6-dimethylpyridin-2-yl)amino]cyclohexyl}-4-fluorobenzamide hydrochloride (112 mg) as a colorless powder.1H NMR (300 MHz, CDCl3, delta): 1.70-2.01 (m, 8H), 2.19 (s, 3H), 2.53 (s, 3H), 3.74-3.84 (m, IH), 4.04-4.20 (m, IH), 6.56 (d, J= 9.0 Hz, IH), 6.63 (d, J= 8.9 Hz, IH), 7.18 (t, J= 8.6 Hz, IH), 7.59 (d, J= 8.9 Hz, IH), 7.67-7.74 (m, IH), 7.94 (dd, J= 7.1, 2.3 Hz, IH), 8.71 (d, J= 8.6 Hz, IH), 14.74 (brs, IH); ESI MS m/z 376 [M (free)++l, 100%].

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,72093-13-1, its application will become more common.

Reference:
Patent; TAISHO PHARMACEUTICAL CO., LTD.; ARENA PHARMACEUTICALS, INC.; WO2006/35967; (2006); 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.1201676-03-0, name is 4,6-Dichloro-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-1-one, molecular formula is C7H4Cl2N2O, molecular weight is 203.03, as common compound, the synthetic route is as follows.Application In Synthesis of 4,6-Dichloro-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-1-one

A mixture of 4,6-dichloro-lH,2H,3H-pyrrolo[3,4-c]pyridin-l-one (200 mg, 1.0 mmol, 1 eq), bromo(cyclopropyl)zinc (5.9 mL of 0.5M solution in THF, 2.7 mmol, 3 eq), palladium (II) acetate (22 mg, 0.1 mmol, 0.1 eq), 2′-(dicyclohexylphosphanyl)-N2,N2,N6,N6-tetramethyl-[l,r- biphenyl] -2,6-diamine (86 mg, 0.2 mmol, 0.2 eq) and THF (2 mL) was heated at 65 – 75 C for 18 h. After cooling to rt, the reaction was subject to aqueous work-up and chromatography on silica gel to afford 91 mg of the title compound as an off-white solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1201676-03-0, 4,6-Dichloro-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-1-one, and friends who are interested can also refer to it.

Reference:
Patent; NURIX THERAPEUTICS, INC.; BARSANTI, Paul A.; BENCE, Neil F.; GOSLING, Jennifa; SAHA, Anjanabha; TAHERBHOY, Asad M.; ZAPF, Christoph W.; BOYLE, Kathleen; CARDOZO, Mario; MIHALIC, Jeffrey; LAWRENZ, Morgan; GALLOP, Mark; BRUFFEY, Jilliane; CUMMINS, Thomas; ROBBINS, Daniel; TANAKA, Hiroko; WANG, Chenbo; COHEN, Frederick; PALMER, Wylie; SANDS, Arthur T.; SHUNATONA, Hunter; (968 pag.)WO2019/148005; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 4021-08-3, 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. 4021-08-3, name is 4-Methylpicolinic acid. A new synthetic method of this compound is introduced below.

Step 3. The preparation of 4-methyl-pyridine-2-carboxylic acid methyl ester: 4-Methyl-pyridine-2-carboxylic acid (4.39 g, 25.3 mmol) was suspended in THF. A solution of diazomethane (60 mL, 0.43 M) in THF was added dropwise and the reaction was stirred for three hours. Several drops of AcOH were added to quench the reaction, then saturated bicarbonate solution was added. The reaction was diluted with EtOAc and the layers were separated. The aqueous layer was washed twice with EtOAc and the organic layers were combined, dried over Na2SO4, and concentrated. The residue was chromatographed on silica gel eluding with 4% MeOH/CH2Cl2 to give 1.17 g (31%) of the desired product as an oil. MS: 152 (M+1 for C8H9N1O2); 1H-NMR (CDCl3)delta2.40 (s, 3 H), 3.97 (s, 3 H), 7.26 (d, 1 H, J=4.2 Hz), 7.94 (s, 1 H), 8.56 (d, 1 H, J=4.9 Hz).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,4021-08-3, 4-Methylpicolinic acid, and friends who are interested can also refer to it.

Reference:
Patent; Warner-Lambert; US6251919; (2001); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem