Month: April 2022

Electric Literature of 1044872-40-3 ,Some common heterocyclic compound, 1044872-40-3, molecular formula is C7H6Cl2N2O2, 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.

In a 500-mL flask with a reflux condenser was added methyl 2-amino-4.6-dichloropyridine-3-carboxylate (22.5 g, 0.101 mol) and 25 wt % sodium methoxide in methanol (88 mL, 0.407 mol), together with methanol (20 mL). The mixture was heated to reflux for 5 hours, then cooled to room temperature. Acetic acid (15 mL) was added to the mixture and pH was adjusted to approximately 7. Methanol was removed and the residue was poured into water (100 mL). The precipitated solid was filtered and further rinsed with water (3*200 mL) to give methyl 2-amino-4,6-dimethoxypyridine-3-carboxylate (18.5 g, 86.4%)

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. 1044872-40-3, Methyl 2-amino-4,6-dichloronicotinate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; RVX Therapeutics Inc.; McLure, Kevin G.; Young, Peter R.; US2013/281398; (2013); 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. 1033203-41-6, name is 6-Bromopyridine-3,4-diamine, the common compound, a new synthetic route is introduced below. Recommanded Product: 6-Bromopyridine-3,4-diamine

To a stirred solution of 6-bromopyridine-3,4-diamine (1.5 g, 8 mmol) in triethylorthoformate (7.11 g, 48 mmol) was added acetic anhydride (7.35 g, 72 mmol)) and stirred at 90C for 6h. The reaction mixture was cooled and evaporated to dryness, then 10 mL 10N NaOH solution was added and heated the contents at 60 C for 50 min. After reaction mixture was cooled acidified with AcOH to a pH 6, then added crushed ice stirred for 15 minutes precipitated solid was filtered. The precipitated solid was washed with n-pentane to get 6-bromo-3H- imidazo[4,5-c]pyridine (1.5 g, 94%) as pale brown solid. LC-MS (method 32): Rt = 0.26 min; m/z = 198.0 (M+H+).

The synthetic route of 1033203-41-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ORYZON GENOMICS, S.A.; SALAS SOLANA, Jorge; CARCELLER GONZALEZ, Elena; ORTEGA MUNOZ, Alberto; (195 pag.)WO2018/149986; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 940911-03-5 ,Some common heterocyclic compound, 940911-03-5, molecular formula is C8H5NO, 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.

C . 5 – { [4-(5 ,5 -Dimethyl- 1 ,3 ,2-dioxaborinan-2-yl)phenyl] ethynyl} pyridine -2- carbaldehyde; To an argon purged solution of 2-(4-iodophenyl)-5,5-dimethyl-l,3,2- dioxaborinane (Method 3, step A) (15 g, 48 mmol) in acetonitrile was addedPdCl2(PPh3)2 (0.7 g, 9.5 mmol) and CuI (0.09 g, 4.7 mmol) at room temperature. The resulting solution was stirred under argon for 10 min. Triethylamine (20 mL, 142 mmol) followed by 5-[(trimethylsilyl)ethynyl]pyridine-2-carbaldehyde (8.1 g, 62mmol) were added and the reaction mixture was then stirred at 85 0C for 2 h. The reaction mixture was concentrated under reduced pressure and then ice-cold water was added. The precipitated solid was stirred as a suspension and was then filtered and washed with water followed by pet-ether to provide 5-{[4-(5,5-dimethyl-l,3,2-dioxaborinan-2- yl)phenyl]ethynyl}pyridine-2-carbaldehyde (15 g, 99%) as brown solid. LC-MS: [M+H]+ 3201H NMR (400 MHz, CDCl3) delta: ppm 10.08 (s, IH), 8.89 (s, IH), 7.95 (m, 2H), 7.82 (d, 2H), 7.55 (d, 2H), 3.78 (s, 4H), 1.03 (s, 6H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,940911-03-5, its application will become more common.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; BENENATO, Kerry, Ellen; CHOY, Allison, Laura; HALE, Michael, Robin; HILL, Pamela; MARONE, Valerie; MILLER, Matthew; WO2010/100475; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 60154-05-4 ,Some common heterocyclic compound, 60154-05-4, molecular formula is C6H6INO, 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: A mixture of potassium fluoride (0.15g, 2.6mmol) and copper iodide (I) (0.50g, 2.6mmol) was heated under reduced pressure until a greenish color appeared, and after cooling to rt, an iodo compound (1.0mmol) in DMF/HMPA (2.5mL each) and trimethyl(trifluoromethyl)silane (0.38mL, 2.6mmol) were added to this flask successively. The mixture was stirred for the specified time and at the indicated temperature (see Table 2). After quenching with satd aqueous ammonium chloride, usual workup and purification by silica gel chromatography yielded the trifluoromethylated product.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,60154-05-4, its application will become more common.

Reference:
Article; Kawasaki-Takasuka, Tomoko; Yamazaki, Takashi; Tetrahedron; vol. 71; 38; (2015); p. 6824 – 6831;,
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. 72093-04-0, name is 3-Chloro-4-methylpyridine, the common compound, a new synthetic route is introduced below. Recommanded Product: 72093-04-0

To a solution of lithium diisopropylamide (6mL, 2M in THF, l2mmol) in 5mL THF at -70C was added under argon a solution of 3-chloro-4-methylpyridine (1 .28g, leq, 1 Ommol) in 5mL THF. The mixture was stirred for 5mm at -70C and then allowed to reach -3 0C. Thereafter the mixture was cooled down to – 70C and a solution of 1-chloro-3,3-dimethylbutan-2-one (2.7g. 2eq, 2Ommol) in 5mL THF was added. Then the mixture was allowed to reach ambient temperature and stirred for lh. Thereafter the mixture wascooled to 0C and saturated aqueous ammonium chloride solution was added. After extraction with ethyl acetate and evaporation of the solvent the cmde material was purified via column chromatography over silica gel (eluent cyclohexane ethyl acetate gradient). After evaporation of the solvent 2g (8 1%) of 4-[(2- tert-butyloxiran-2-yl)methyl]-3-chloropyridine were obtained as colourless oil.MS (ESI): 226.1 ([M+H]+)

The synthetic route of 72093-04-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER CROPSCIENCE AG; HOFFMANN, Sebastian; SUDAU, Alexander; DAHMEN, Peter; WACHENDORFF-NEUMANN, Ulrike; BERNIER, David; BRUNET, Stephane; LACHAISE, Helene; VIDAL, Jacky; GENIX, Pierre; COQUERON, Pierre-Yves; GEIST, Julie; VORS, Jean-Pierre; KENNEL, Philippe; MILLER, Ricarda; WO2014/167010; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 87674-15-5, 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. 87674-15-5, name is 1-(3-Fluoropyridin-4-yl)ethanol, molecular formula is C7H8FNO, 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-(3-fluoropyridin-4-yl)ethanol (10 g, 70.3 mmol) and commercial activated MnO2 (8 g, 92.1 mmol) in toluene (100 mL) were refluxed until disappearance of starting material. After cooling, the mixture was filtered on a bed of celite, the cake washed with toluene and the organic phases concentrated to give 3-fluoro-4-acetyl pyridine (6.9 g, 70%) that was used directly in the next step.

According to the analysis of related databases, 87674-15-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Pharmacia Italia S.p.A.; US2007/142415; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1256808-59-9 , The common heterocyclic compound, 1256808-59-9, name is 5-Fluoro-3-methylpicolinic acid, molecular formula is C7H6FNO2, 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 tert-butyl ((3aS,4R,8R)-4-(6-amino-3-fluoropyridin-2-yl)-4,7,7- trimethyl-8-oxido-3,3a,4,7-tetrahydro-2H-isothiazolo[l,5-a][l,4]thiazin-6-yl)carbamate (Int- 39AB, 150 mg, 0.35 mmol) in THF (20 mL) was added 5-fluoro-3-methylpicolinic acid (82 mg, 0.53 mmol) followed by T3P (1.1 g, 1.75 mmol, 50% in ethyl acetate), and diisopropylethylamine (267 mg, 2.1 mmol). The reaction was stirred at 70 C for 4 h. After that, the reaction mixture was diluted with aqueous saturated sodium hydrogencarbonate solution (20 mL) and extracted with ethyl acetate (3 x 30 mL). The combined organic layers were dried over sodium sulfate, filtered and concentrated to give a crude product. The crude was purified by column chromatography (silica gel, eluting with petroleum ether / ethyl acetate 1: 1) to yield, after drying in vacuo, the title compound as a yellow solid (130 mg, 66% yield). XH NMR (CDC13, 400 MHz): delta 1.50-1.59 (m, 1 H), 1.66 (s, 9 H), 1.86 (s, 3 H), 1.97 (s, 3 H), 2.06-2.12 (m, 1 H), 2.14 (s, 3 H), 2.84 (s, 3 H), 3.54 (dd, J = 7.7, 10.7 Hz, 1 H), 3.69 (ddd, J = 4.8, 10.7, 10.7 Hz, 1 H), 4.30 (ddd, / = 2.1, 7.1, 12.0 Hz, 1 H), 7.40 (dd, J = 2.1, 8.9 Hz, 1 H), 7.58 (dd, = 9.1, 10.0 Hz, 1 H), 8.31 (d, J = 2.6 Hz, 1 H), 8.49 (dd, / = 3.1, 8.9 Hz, 1 H), 10.78 (s, 1 H), 12.54 (s, 1 H). MS (ES+) m/z 563.2 [M+H].

The synthetic route of 1256808-59-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; BARTELS, Bjoern; CUENI, Philipp; DOLENTE, Cosimo; GUBA, Wolfgang; HAAP, Wolfgang; KUGLSTATTER, Andreas; OBST SANDER, Ulrike; PETERS, Jens-Uwe; ROGERS-EVANS, Mark; VIFIAN, Walter; WOLTERING, Thomas; (231 pag.)WO2016/55496; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1159812-31-3, 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 1159812-31-3, name is 7-Bromo-2-methyl-[1,2,4]triazolo[1,5-a]pyridine. This compound has unique chemical properties. The synthetic route is as follows.

To boronic acid ester compound having triazole side chain (23, 2.63 g) and 7-bromotriazolopyridine derivative (24, 2.15 g, prepared as described in Example 4 using compound 18 of Example 5) in dioxane (50 mL) and water (12 mL), Na2CO3 (2.47 g) and Pd(Ph3P)4 (821 mg) were added and the reaction mixture was heated at 90 C. to 100 C. for 1.5 hours. The solvent was then removed under reduced pressure to reduce the volume by half, and water was added. After the resulting precipitate was filtered and dissolved in ethanol, 1.95 g of colorless compound 25 was precipitated (73%).Compound 25: 1H-NMR (300 MHz, DMSO-d6) 2.48 (br s, 3H), 3.96 (dd, 9.5, 6, 1H), 4.30 (dd, 9.5, 9.5, 1H), 4.86 (d, 5, 2H), 5.19 (ddt, 9.5, 6, 5, 1H), 7.30 (ddd, 7, 1.5, 1.5, 1H), 7.42 (dd, 8.5, 2, 1H), 7.58 (dd, 14, 2, 1H), 7.74 (dd, 8.5, 8.5, 1H), 7.77 (d, 1, 1H), 7.86 (br s, 1H), 8.18 (d, 1, 1H), 8.88 (d, 7, 1H);LRMS m/z 393 (M+, 7), 349 (14), 320 (6), 279 (8), 242 (10), 158 (11), 108 (21), 80 (29), 53 (100).

According to the analysis of related databases, 1159812-31-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Katoh, Issei; Aoki, Toshiaki; Suzuki, Hideyuki; Utsunomiya, Iwao; Kuroda, Norikazu; Iwaki, Tsutomu; US2011/98471; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 78686-77-8, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 78686-77-8 as follows.

Example 38 – Preparation of Intermediate 13 [ 00277 ] The synthesis of Intermediate 13 followed General Procedure 11 following: General Procedure 11 Intermediate 12 Intermediate 13 [ 00278 ] To a cold (0C) solution of 3-(5-amino-lH-pyrazol-3-yl) pyridine- 2(lH)-one (Intermediate 11, 9.0 g, 0.036 mol, 1 eq) in methanol (25 mL) was added sodium methoxide (25% in methanol, 15.5 mL, 0.072 mol, 2 eq). The reaction was stirred for 2 hours at room temperature. After completion of reaction, the reaction mixture was evaporated under reduced pressure, and the residue was poured into ice cold water under stirring. This mixture was extracted with ethyl acetate. The organic layer was dried over sodium sulpfate and concentrated under reduced pressure. The residue was purified by column chromatography using neutral silica gel, eluting with 25-30% ethyl acetate in hexane to give pure desired product (7.5 g, yield-84.74%>) m/z[M+H]+ 246.17 1H NMR (DMSO-d6, 400 MHz) delta 8.73 (d, J = 1.5 Hz, 1H), 8.41 (d, J= 1.5 Hz, 1H), 4.02 (d, J= 1.1 Hz, 3H), 3.86 (d, J= 1.1 Hz, 3H) ppm.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,78686-77-8, its application will become more common.

Reference:
Patent; VERSEON CORPORATION; SHORT, Kevin Michael; KITA, David Ben; ESTIARTE-MARTINEZ, Maria de los Angeles; PHAM, Son Minh; (244 pag.)WO2016/44662; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 914349-75-0, name is 5-(4-Fluorophenyl)picolinonitrile, molecular formula is C12H7FN2, 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. SDS of cas: 914349-75-0

5-(4-fluorophenyl)picolinonitrile (1.5 g) was dissolved in dry THF (20 mL) and cooled in an ethanol / CO2 bath. 1 M LiAlH4 in THF (20 mL) was added and the mixture stirred at below room temperature for 2 h. The reaction was quenched by the dropwise addition of 1 : 10 water : THF (20 mL), diluted with ethyl acetate, stirred with 1 M NaOH and the organic phase decanted, washed with 1 M NaOH, brine and dried. Evaporation gave the title compound as an amorphous yellow solid, used immediately and without further purification.

With the rapid development of chemical substances, we look forward to future research findings about 914349-75-0.

Reference:
Article; Greig, Iain R.; Baillie, Gemma L.; Abdelrahman, Mostafa; Trembleau, Laurent; Ross, Ruth A.; Bioorganic and Medicinal Chemistry Letters; vol. 26; 18; (2016); p. 4403 – 4407;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem