Month: April 2022

Adding a certain compound to certain chemical reactions, such as: 1079179-12-6, 2-Chloro-3-fluoro-5-nitropyridine, 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, COA of Formula: C5H2ClFN2O2, blongs to pyridine-derivatives compound. COA of Formula: C5H2ClFN2O2

General procedure: To a solution of Compound 4 (2 g, 8.58 mmol, 1 eq) in CH3CN (30 mL) was added CS2CO3 (5.59 g, 17.15 mmol, 2 eq) in one portion at 20 C. After stirring at 20 C for 30 min, 2,3- dichloro-5-nitro-pyridine (1.82 g, 9.43 mmol, 1.1 eq) was added. The mixture was stirred at 20 C for 36 h. The reaction mixture was filtered and the filter cake was washed with 100 mL of EtOAc. The filter cake diluted with water (100 mL) and extracted with DCM (3 x 150 mL). The combined DCM extracts were washed with aq saturated NaCl (10 mL), filtered, and concentrated under reduced pressure to give crude Compound 6 as a yellow solid (1.8 g, 53.85% yield). 1H NMR (400 MHz, DMSO-d6) d 9.03 (d, 1H), 8.99 – 8.95 (m, 2H), 8.26 (s, 1H), 7.64 (s, 1H), 7.42 (d, 1H), 3.99 (s, 3H), 3.82 (s, 3H); MS (El) for C17H12CIN3O6, found 389.9 (MH+).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1079179-12-6, 2-Chloro-3-fluoro-5-nitropyridine, and friends who are interested can also refer to it.

Reference:
Patent; EXELIXIS, INC.; BANNEN, Lynne Canne; BUI, Minna; JIANG, Faming; WANG, Yong; XU, Wei; (235 pag.)WO2019/148043; (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. 1149-24-2, name is Diethyl 2,6-dimethylpyridine-3,5-dicarboxylate, the common compound, a new synthetic route is introduced below. Safety of Diethyl 2,6-dimethylpyridine-3,5-dicarboxylate

General procedure: To a mixture of ethyl acetoacetate or methyl acetoacetate (1 eqv), formaldehyde (1.1 eqv) and NH4OAc (1.5 eqv) in acetic acid (3 mL) was added FeWO4 (20 mol%) at room temperature and the mixture was heated at 80 C for 2 h (monitoring by TLC) to give poly-substituted pyridine (3), to this solution isatin (1 eqv) was added and heating continued at same temperature for 3 h (monitoring by TLC). After that the reaction mixture was cooled to room temperature neutralized with sodium bicarbonate and extracted with EtOAc (2 × 10 mL). The organic layers were washed with brine, dried using sodium sulphate .Evaporation of the solvent gave the crude product which was purified by silica gel column chromatography. Elution of the column with petroleum ether-EtOAc gave the desired product.

The synthetic route of 1149-24-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Paplal, Banoth; Nagaraju, Sakkani; Sathish, Kota; Kashinath, Dhurke; Catalysis Communications; vol. 103; (2018); p. 110 – 115;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1221171-70-5 ,Some common heterocyclic compound, 1221171-70-5, molecular formula is C6H3ClF3NO, 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 LDA (2 M, 2.5 mL) in THF ( 27.0 mL) was added dropwise a solution of 2-chloro-6-(trifluoromethoxy)pyridine (900 mg, 4.6 mmol) in THF (9.0 mL) at -78C under N2. The mixture was stirred at -78C for 2 h. A solution of I2 (1.3 g, 5.0 mmol, 1.0 mL) in THF (9.0 mL) was added at -78C. Then the mixture was slowly warmed to 25C and stirred for 12 h. The reaction was quenched with saturated H4C1 (15.0 mL) and extracted with ethyl acetate (15.0 mL chi 3). The combined organic phase was washed with brine (15 mL chi 3), dried over anhydrous Na2S04, filtered and concentrated to give a residue. The residue was purified by prep-TLC (Si02) to give 6-chloro-3-iodo-2-(trifluoromethoxy)pyridine (1.2 g, 3.0 mmol, 65.2% yield). 1H MR (400MHz, CHLOROFORM-i ) delta 8.10 (d, J= 8.1 Hz, 1H), 7.03 (d, J= 8.1 Hz, 1H).

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. 1221171-70-5, 2-Chloro-6-(trifluoromethoxy)pyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; QUENTIS THERAPEUTICS, INC.; VACCA, Joseph P.; LI, Dansu; BETTIGOLE, Sarah; (184 pag.)WO2018/222918; (2018); 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. 936841-69-9, name is 4-(Trifluoromethyl)picolinonitrile, the common compound, a new synthetic route is introduced below. Quality Control of 4-(Trifluoromethyl)picolinonitrile

To a solution of 4-(trifluoromethyl)pyridine-2-carbonitrile (0.516 g, 3.00 mmol) in methanol (4.5 ml) was added sodium methoxide (30 wt% in MeOH) (0.027 g, 0.150 mmol, 0.028 ml). The mixture was stirred at room temperature for 3 h. The solution was transferred into a reaction vial, methylamine (33 wt% inEtOH) (1.512 g, 16.07 mmol, 2.0 ml) was added, the vial was closed and the mixture was heated at60C overnight. Hydrochloric acid (4M in dioxane) (3.00 mmol, 0.750 ml) was added and heating was continued at 90C for 2 h. The reaction mixture was concentrated. In a reaction vial, the residue was redissolved in methylamine (33 wt% in EtOH) (7.56 g, 80 mmol, 10.00 ml), hydrochloric acid (4M in dioxane) (3.00 mmol, 0.750 ml) was added, the vial was capped and the mixture was heated at 90Covernight. The reaction mixture was concentrated and the residue partitioned between diethyl ether and sat. Na2CO3 (aq). After washing and separation of the phases, the aqueous layer was extracted with ether two more times. The combined organic layers were dried over sodium sulfate and concentrated. The residue was purified over silica by flash column chromatography (0-100% B in A; A: CH2CI2 B: CH2CI2/MeOH/Et3N, 9/1/0.1). The fractions containing product were combined andconcentrated. The residue was dissolved in methanol and hydrochloric acid in dioxane (4M, 2 ml) was added. The mixture was concentrated, coevaporated with methanol and twice with diethyl ether to afford the title compound (484 mg) as a solid. LCMS (method 1): 218 (M+H), retention time 1.47 mm. 1H-NMR (DMSO-d6, ppm) 2.86 (3H), 3.06 (3H), 8.15 (1H), 8.29 (1H), 9.09 (1H), 9.87 (1H), 10.23 (1H).

The synthetic route of 936841-69-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; MUEHLEBACH, Michel; TITULAER, Ruud; EMERY, Daniel; EDMUNDS, Andrew; STOLLER, Andre; JUNG, Pierre Joseph Marcel; BUCHHOLZ, Anke; RENOLD, Peter; (98 pag.)WO2015/144826; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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 72587-18-9, name is 2-Chloro-5-(trifluoromethyl)pyridin-3-amine. This compound has unique chemical properties. The synthetic route is as follows. Computed Properties of C6H4ClF3N2

[0276] [B] N- (2-Chloro-5- (trifluoromethyl) pyridin-3-yl) acetamide [0277] [0278] A mixture solution of 2-chloro-5- (trifluoromethyl) pyridin-3-amine (75 g, 381.6 mmol) and Ac2O (82.5 mg, 808.1 mmol) in pyridine (200 mL) was stirred at 80 for 16 h. After cooling to room temperature, it was diluted with EtOAc (500 mL), washed with water and brine. The organic layer was dried over anhy. Na2SO4, filtered, and concentrated in vacuo to give a crude product, which was first purified by silica gel flash chromatography (petroleum etherEtOAc 51) and then crystallization in petroleum ether (100 mL) to afford the title compound (65 g, mixture of mono-and bis-Ac protected product, 73yield) as white solids. MS239.0 [M+H] +.N- (2-Methyl-5- (trifluoromethyl)pyridin-3-yl) acetamide[0280][0281]To a mixture of N- (2-chloro-5- (trifluoromethyl) pyridin-3-yl) acetamide and N-acetyl-N- (2-methyl-5- (trifluoromethyl) pyridin-3-yl) acetamide (35 g 146.7 mmol) K2CO3(62.2 g 450 mmol) methyl boroxine (50in ether 70 g 278.8 mmol) and X-phos (14.4 g 43mmol) in MeCN (250 mL) and water (150 mL) was added Pd (OAc)2(3.4 g 15.1 mmol) And the resulting reaction mixture was stirred at 100 for 16 h. After cooling to room temperature The reaction was diluted with EtOAc (300 mL) washed with water (300 mL) and brine (300 mL) . The organic layer was dried over anhy. Na2SO4 filtered and concentrated in vacuo to give a crude product which was then purified by silica gel flash chromatography (petroleum etherEtOAc51) to afford the title compound (20 g 57yield) as a gray solid. MS 219.0 [M+H]+.1H NMR (400MHz CHCl3-d1) delta 8.62 (s 1H) 8.54 (s 1H) 7.11 (br 1H) 2.60 (s 3H) 2.28 (s 3H) .

With the rapid development of chemical substances, we look forward to future research findings about 72587-18-9.

Reference:
Patent; SAVIRA PHARMACEUTICALS GMBH; EUROPEAN MOLECULAR BIOLOGY LABORATORY; TAN, Xuefei; WANG, Lisha; CUMMING, John Graham; LIU, Yongfu; WU, Jun; LI, Dongbo; SHEN, Hong; SHI, Tianlai; (179 pag.)WO2017/133657; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 800401-70-1, Ethyl 5-bromo-1H-pyrrolo-[2,3-c]-pyridine-2-carboxylate, 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, Formula: C10H9BrN2O2, blongs to pyridine-derivatives compound. Formula: C10H9BrN2O2

To a solution OF 5-BROMO-LH-PYRROLO [2,3-c] pyridine-2-carboxylic acid ethyl ester (Preparation 26,0. 160g, 0. 590MMOL) in DMF (anhydrous, 5ML) was added zinc (II) cyanide (0.041g, 0.35mmol) then tetrakis-triphenylphosphine palladium (0). The reaction mixture was degassed by bubbling argon through it for l Omin. The reaction mixture was heated to reflux temperature for 4. 5h then allowed to cool to rt. Water (30mL) was added and the mixture extracted with ethyl acetate (2X50ML). The combined organics were washed with brine (30mL), dried (MGS04), filtered and concentrated in vacuo. The residue was dissolved in ethyl acetate then adsorbed onto silica gel. Purification via flash column chromatography (SI02, ethyl acetate: isohexane, 1: 3, v/v) gave the title compound as a white solid. aH (CDCl3): 1.45 (3H, t), 4.49 (2H, quartet), 7.31 (1H, s), 8.09 (1H, s), 8.97 (1H, s), 9.60 (1H, br s); M/Z (ES+) = 216 [M+ H] + ; RT = 3. 03MIN.

The synthetic route of 800401-70-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; OSI PHARMACEUTICALS, INC.; WO2004/104001; (2004); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 116855-08-4, 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 116855-08-4, name is 1H-Pyrazolo[3,4-b]pyridine-3-carboxylic acid. This compound has unique chemical properties. The synthetic route is as follows.

Step 5 To a solution of 1H-pyrazole[3,4-b]pyridine-3-carboxylic acid (XIII) (0.39 g, 2.4 mmol) in dry MeOH (10 mL) was added concentrated H2SO4 (4 drops) and refluxed for 6 h under nitrogen. The solution was cooled and the solvent was evaporated under vacuum. The residue was partitioned between DCM and saturated aqueous NaHCO3 solution. The organic layer was separated, dried over MgSO4, filtered and concentrated under reduced pressure. The crude product was purified on a flash silica gel column (100% DCM?3:97 MeOH:DCM) to produce methyl 1H-pyrazolo[3,4-b]pyridine-3-carboxylate (XIV) as a white solid (382 mg, 2.16 mmol, 90% yield). 1H NMR (CDCl3) delta ppm 4.08 (s, 3H), 7.38 (m, 1H), 8.63 (dd, J=8.10 Hz, J=1.51 Hz, 1H), 8.72 (dd, J=4.62 Hz, J=1.41 Hz, 1H); ESIMS found for C8H7N3O2 m/z 178.2 (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 116855-08-4, 1H-Pyrazolo[3,4-b]pyridine-3-carboxylic acid.

Reference:
Patent; Samumed, LLC; KC, Sunil Kumar; Wallace, David Mark; Cao, Jianguo; Chiruta, Chandramouli; Hood, John; (264 pag.)US2016/68550; (2016); 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. 628691-93-0, name is 2-Chloro-3-fluoroisonicotinic acid, the common compound, a new synthetic route is introduced below. Computed Properties of C6H3ClFNO2

Example 125: 3-(4-Bromo-2-fluoro-phenylamino)-2-chloro-isonicotinic acid; 2-Chloro-3-fluoro-isonicotinic acid (200mg, 1.14mmol) and 4-bromo-2-fluoroaniline (217mg, 1.14mmol) were added to 5ml of dry THF and the mixture was cooled to -78 0C. LiHMDS (1 M in THF, 4.0ml) was added and the mixture was allowed to warm to room temperature over night. Solid ammonium hydrochloride (1g) was added and after 1h the mixture was filtered and the volatiles were removed in vacuo. The crude material was purified by flash-chromatography using a gradient of 0-12% methanol (containig 0.5% EPO formic acid) in DCM as eluent to give 213mg (0.617mmol; 54% yield) of pure desired carboxylic acid product. LC-MS (method IiI): rt = 4.42min; m/z [M+H]+ 386/388.

The synthetic route of 628691-93-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; APPLIED RESEARCH SYSTEMS ARS HOLDING N.V.; WO2006/45514; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 135900-33-3, 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.135900-33-3, name is 6-(Trifluoromethoxy)pyridin-3-amine, molecular formula is C6H5F3N2O, molecular weight is 178.11, as common compound, the synthetic route is as follows.

[0289] Quinoline-7-carboxylic acid (70 mg, 0.404 mmol, 1.0 eq) and 6- (trifluoromethoxy)-pyridin-3-amine (79 mg, 0.44 mmol, 1.1 eq) were dissolved in 1 mL of DMF and the resulting mixture was cooled down to 0 C. HATU (168 mg, 0.44 mmol, 1.1 eq) and DIPEA (0.144 mL, 0.808 mmol, 2.0 eq) were added at 0 C, and then the reaction mixture was allowed to warm up to room temperature and stirred at room temperature for 4 hrs. The progress of the reaction was monitored by LCMS and TLC. Upon completion, the reaction mixture was poured into ice-cold water. The formed solid was filtered, washed and dried in vacuo to give 20 mg of the desired compound 126 as a pale-yellow solid in 15% yield. 1H NMR (400 MHz, CDC13): delta 9.03-9.02 (dd, J = 2.8 Hz, 1.6 Hz, 1H), 8.57 (s, 1H), 8.48 (s, 1H), 8.46-8.45 (d, J = 2.8 Hz, 1H), 8.26 (s, 1H), 8.24 (brs, 1H), 8.09-8.12 (dd, J = 8.8 Hz, 1.6 Hz, 1H), 8.0-7.97 (d, J = 8.8 Hz, 1H), 7.56-7.52 (dd, J = 8.4 Hz, 4.4 Hz, 1H), 7.12-7.10 (d, J = 8.8 Hz, 1H). 99.15% purity by LCMS; m/z =334.19 [M+H]+.

Statistics shows that 135900-33-3 is playing an increasingly important role. we look forward to future research findings about 6-(Trifluoromethoxy)pyridin-3-amine.

Reference:
Patent; ACTAVALON, INC.; DNEPROVSKAIA, Elena, V.; HOLZWARTH, Michael, S.; RYCHNOVSKY, Scott, D.; (184 pag.)WO2018/85348; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 6515-09-9, 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 6515-09-9, name is 2,3,6-Trichloropyridine. This compound has unique chemical properties. The synthetic route is as follows.

557.8g 2,3,6-trichloropyridine, which is obtainedby the chlorination, 123.5g triethylamine, 8.4g palladium-carbon and 1673g toluene are added to a reactorfor one time, then heated to 60?80C, and hydrogen gasis introduced to proceed hydrogenating. When pH valueof the reaction solution reaches 4?8, stopping introduci After the aforementioned reaction solution wascooled to room temperature, 420g water is added for dissolvingtriethylamine hydrochloride. Then the reactionsolution is filtered, and the cake which is palladium carbonwashed by 30g water and 30g toluene can be recycled.The filtrate is allowed to stand stratification, andthen the toluene layer is extracted by 200g hydrochloricacid at least three times after the water was separated.The extracted solution can be recycled for the next batchwith replenishing 2,3,6-trichloropyridine and toluene. Thehydrochloride layers are combined and diluted by 1630gwater after extraction, and then solid is crystallized. Thesolid is washed by 100g water (the waste water can berecycled for extraction) after filtration, then wet 2,3-dichloropyridine is given. Dry product of 2,3-dichloropyridineis given by drying the wet product. Finally, 387.7gproduct is totally gained when the waste water is recycled,and the yield is 85.7%, the purity is greater than orequal to 99.5%.

According to the analysis of related databases, 6515-09-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Lianhe Chemical Technology Co., Ltd.; Jiangsu Lianhe Chemical Technology Co., Ltd; WANG, Ping; FAN, Xiaobin; ZHANG, Juntao; YE, Fangsheng; EP2687510; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem