Day: April 11, 2022

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. 138588-22-4, name is 3-(Pyridin-2-yl)-1,2,4-thiadiazol-5-amine, the common compound, a new synthetic route is introduced below. SDS of cas: 138588-22-4

3-Pyridin-2-yl-[l,2,4]thiadiazol-5-ylatnine (50 mg, 0.28 mmol) was placed in a vial and dissolved in dioxane (1.5 mL) and then added 3 N NaOH (1.5 mL), Then 4- methyithiophene-2-carboxiyl chloride (45 mg, 0.28 mmol) was added and the reaction heated to 50 C for 16 h. The reaction was then diluted with water and acidified with AcOH to force precipitation. The precipitates were collected by filtration. The collected solid was redissolved and concentrated onto celite (5 g). Then purified by normal phase chromatography (solvent A CH2C12, solvent B CH2Cl2/MeOH/ H40H 90: 10: 1, gradient from 0 – 60% B). Collected the desired product (72 mg, 0.24 mmol, 86%). NMR (400 MHz, DMSO-rf6) delta pm 2.25 (s, 3 H) 7.49 (ddd, J=7.55, 4.75, 1.12 Hz, 1 H) 7.65 (s, 1 H) 7.95 (id, J-7.74, 1.81 Hz, 1 H) 8.13 (d, ,/ 1.02 Hz, 1 H) 8.20 (d, J-7.91 Hz, 1 H) 8.62 – 8.74 (m, 1 H) 13.75 (br. s., i H); LCMS (M/Z): M i i 303.

The synthetic route of 138588-22-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SCYNEXIS INC.; LIU, Hao; SLIGAR, Jessica, Marie; SPEAKE, Jason, Daniel; MOORE, Joseph, A., III; BECK, Brent, Christopher; WO2015/73797; (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 17570-98-8, name is 2-(Bromoacetyl)pyridine hydrobromide. This compound has unique chemical properties. The synthetic route is as follows. SDS of cas: 17570-98-8

NaH (60%) (120 mg, 3 mmol) was added into a solution of dichloro-2- (2,2,2-trifluoro-ethyl)-1 H-benzoimidazole (269 mg, 1 mmol) in DMF (5 ml) at O0C. The resulting mixture was stirred at 0C for half hour. 2-bromo-1 -(2- pyridiny)-l-ethanone hydrobromide (421.4 mg, 1.5 mmol) was then added to the reaction mixture at 0C. The reaction temperature was raised to 25C and then the reaction mixture was stirred for 18 hours. NH4CI (aq.) was added and extracted with EtOAc. The organic layer was washed with brine, then dried over anhydrous MgSO^ The solvent was distilled out under reduced pressure. Column chromatography (silica gel, EtOAc / hexanes 0% to 70%) yielded the title compound as a yellow solid.MS m/z (M+H) 388, (M-H) 386.

With the rapid development of chemical substances, we look forward to future research findings about 17570-98-8.

Reference:
Patent; JANSSEN PHARMACEUTICA N.V.; WO2006/39215; (2006); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 75806-86-9, 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. 75806-86-9, name is 2-Bromo-5-chloro-3-nitropyridine, molecular formula is C5H2BrClN2O2, 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.

Example 2: 2-Bromo-5-chloro-pyridin-3-ylamine; [00382] 2-Bromo-5-chloro-3-nitro-pyridine (11.87 g, 50 mmol) was dissolved in 100 mL ether. Tin(ll) chloride dihydrate (56.4g, 0.5 mol) was dissolved in 100 mL of concentrated hydrochloric acid and added drop wise over 15 minutes to the stirring ethereal solution of the nitro compound. The exothermic reaction brought the ether to boiling and it was allowed to evaporate off. After the addition was complete the reaction mixture was placed on a 50 C oil bath and stirred for 30 minutes to boil of the remaining ether. The flask was then cooled on in an ice bath. The precipitate formed was collected and by filtration and dissolved in 100 mL of water. The pH was adjusted to 9-10 by the addition of concentrated ammonium hydroxide solution and the product was extracted with ethyl acetate (2 x 100 mL). The organic layer was washed with diluted ammonium hydroxide, water and brine and dried over Na2SU4 and the solvent was evaporated to afford 7.4 g of tan crystalline solid. MS m/z : 208.9 (M+H).

According to the analysis of related databases, 75806-86-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CHEMOCENTRYX, INC.; WO2006/76644; (2006); A2;,
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. 2546-56-7, name is 4-Chloro-3-fluoropyridine, the common compound, a new synthetic route is introduced below. HPLC of Formula: C5H3ClFN

To a solution of 4-chloro-3-fluoropyridine (10 mmol) in anhy THF and MeOH (15ml: 15ml) was added sodium methoxide (25% in MeOH, 10.5 mmol) dropwise. The mixture was refluxed overnight until the reaction completed (monitored by TLC). The mixture was poured into 100ml water and extracted with DCM (100ml x 3). The organic extract was dried over Na2SO4 and concentrated. The residue was purified by chromatography (eluent: ethyl acetate), to give a colorless liquid (55%).

The synthetic route of 2546-56-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BTG INTERNATIONAL LIMITED; WO2009/103950; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 709652-82-4, 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. 709652-82-4, name is 2-Amino-5-bromonicotinonitrile, molecular formula is C6H4BrN3, 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.

Int-136 (0.058 mmols, 0.040 g) and 2-amino-5-bromonicotinonitrile (0.098 mmols, 0.020 g) were added to a 5mL microwave vessel equipped with a magnetic stir bar. Dioxane (2 mL) and saturated NaHC03(aq) (1 mL) were then added and the reaction vessel was flushed with nitrogen gas. PdC12(dppf) (0.023 mmols, 0.017 g) was added, the reaction vessel was sealed and placed in a microwave reactor and heated to 110 oC for 10 minutes. The reaction solution was then poured into water, extracted with ethyl acetate, and washed once with saturated aqueous sodium chloride. The organic layer was collected and subsequently dried with anhydrous Na2SO4 and filtered. This filtrate was collected, concentrated, and dried in-vacuo. This crude material was then purified by preparative LC/MS: (Water/Acetonitrile; 55-80%). The resultant fractions were collected and the solvent was removed in-vacuo affording tert-butyl (2R)-1-(4-(6-amino-5- cyanopyridin-3 -yl)phenyl)-4-(3 -(7-fluoro- 1 -(3 -methoxypropyl)-3 -methyl- 1 H-indol-2- yl)piperidin-1-yl)-4-oxobutan-2-ylcarbamate (Int-137) as a clear oil (0.040 mmols, 0.027 g, 69% yield). ESI-MS: m/z 683.4 (M+H)+.

According to the analysis of related databases, 709652-82-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; BROWN, Jason, W.; KEUNG, Walter; LI, Zhe; TYHONAS, John; WO2010/111634; (2010); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 53554-20-4, 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. 53554-20-4, name is 6-Amino-2-chloronicotinonitrile. A new synthetic method of this compound is introduced below.

38 (500mg, 3.25mmol), phenylboronic acid (595mg, 4.88mmol), K3PO4 (1.73g, 8.14mmol) and Pd(PPh3)4 (0.16mmol) were added to a microwave vial together with toluene/ EtOH (10:1, 11mL). The vial was flushed with N2, sealed and heated under microwave irradiation for 1h at 100C. The reaction mixture was cooled to rt, 1M NaOH (30mL) was added, and the mixture was extracted with EtOAc (2×30mL). The combined organic phase was dried over Mg2SO4 and evaporated under vacuum. Purification by DCVC (heptane/EtOAc 100:0 to 60:40) afforded the product as yellow solid (416mg, 65%). mp 204.1-204.9C. 1H NMR (CDCl3) delta 7.89-7.83 (m, 2H), 7.75 (d, J=8.8Hz, 1H), 7.54-7.47 (m, 3H), 6.50 (d, J=8.8Hz, 1H). 13C NMR (DMSO-d6) delta 161.0, 141.6, 138.0, 129.5, 128.4, 128.2, 119.7, 106.6, 92.2.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,53554-20-4, 6-Amino-2-chloronicotinonitrile, and friends who are interested can also refer to it.

Reference:
Article; Petersen, Jette G.; S°rensen, Troels; Damgaard, Maria; Nielsen, Birgitte; Jensen, Anders A.; Balle, Thomas; Bergmann, Rikke; Fr°lund, Bente; European Journal of Medicinal Chemistry; vol. 84; (2014); p. 404 – 416;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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