Category: pyridine-derivatives

Application of 107504-08-5, 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 107504-08-5, name is 5-Fluoro-2-picolinic acid. This compound has unique chemical properties. The synthetic route is as follows.

5-fluoro-pyridine-2-carboxylic acid methyl ester2.7 mL Thionylchloride was dropped to 5 g 5-fluor-pyridine-2-carboxylic acid in 50 mL methanol. The reaction was stirred for 2 h at 65C in a sealded micro wave vial. The solvents were removed and the residue was desolved in a mixture of DCM and methanol and filtered over silica gel. The filtrate was evaporated to give 5.9 g of the desired product.Rt: 0.77 (method K). (M+H)+: 156

According to the analysis of related databases, 107504-08-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; GRAUERT, Matthias; BISCHOFF, Daniel; DAHMANN, Georg; KUELZER, Raimund; RUDOLF, Klaus; WO2013/79460; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 58530-53-3, 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.58530-53-3, name is 2,4-Dibromopyridine, molecular formula is C5H3Br2N, molecular weight is 236.892, as common compound, the synthetic route is as follows.

A mixture of the bororate C2 (500 mg, 0.643 mmol), 2,4-dibromopyridine (152 mg, 0.643 mmol), tetrakis(triphenylphosphine) palladium (0) (52 mg, 0.045 mmol), 2 M Na2CO3(aq) (0.8 cm3), EtOH (0.8 cm3) and toluene (2 cm3) was degassed and then heated at reflux with a bath temperature of 110 C under argon for 45 h. The mixture was allowed to cool. The two phases were separated. The aqueous layer was extracted with ether (3×4 cm3). The organic layer and the ether extracts were combined, washed with brine (1×7 cm3) and dried over anhydrous sodium sulfate and the solvents were completely removed. Purification by column chromatography over silica gel using DCM-light petroleum (0:1 to 1:0) as eluent gave 140 mg (27%) ofC-3 as a light brown solid; deltaH(200 MHz; CDCl3) 0.82-1.07 (12 H, m, Me), 1.23-1.68 (16 H, m, CH2); 1.69-1.88 (2 H, m, CH), 3.93 (4 H, m, ArOCH2), 7.04 (4 H, m, ArH), 7.43-7.83 (11 H, m, CarH & ArH), 7.97 (1 H, m, PyH), 8.11(1 H, m, PyH), 8.36 ((2 H, m, CarH), and 8.54 (1 H, m, PyH); m/z [APCI+] 805, 806, 807, 808, 809 (M+).

Statistics shows that 58530-53-3 is playing an increasingly important role. we look forward to future research findings about 2,4-Dibromopyridine.

Reference:
Patent; ISIS INNOVATION LIMITED; THE UNIVERSITY COURT OF THE UNIVERSTIY OF ST ANDREWS; WO2004/20448; (2004); A1;,
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Pyridine | C5H5N – PubChem

Related Products of 93683-65-9 ,Some common heterocyclic compound, 93683-65-9, molecular formula is C6H2ClN3O2, 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.

9.1 g of 2-cyano-3-nitro 6-chloro-pyridine was added, and 200 ml of THF, 100 ml of a saturated ammonium chloride solution, and 16.8 g of iron powder were added and reacted at 50 C for 1 h. After completion of the reaction, it was cooled to room temperature, filtered, and the filter cake was washed with ethyl acetate to give an organic solution.The obtained organic solution was washed once with saturated sodium hydrogen carbonate solution and saturated brine, dried over anhydrous sodium sulfate and concentrated to give a product.After drying, weighed 6.8 g.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,93683-65-9, its application will become more common.

Reference:
Patent; Henan Ruida Pharmaceutical Technology Co., Ltd.; Xu Xuejun; Lin Sheng; (8 pag.)CN108623582; (2018); A;,
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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. 6313-54-8, name is 2-Chloroisonicotinic acid, molecular formula is C6H4ClNO2, 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. Recommanded Product: 2-Chloroisonicotinic acid

Step 2 Preparation of Methyl 2-Chloroisonicotinate: To a solution of thionyl chloride (15.0 g, 0.127 mol) in 20 mL of toluene was added 2-chloroisonicotinic acid (10.0 g, 0.063 mol) and the reaction was heated at reflux until gas evolution ceased. Then a solution of methanol (7.7 mL, 0.19 mol) in 10 mL of toluene was added at room temperature over 15 min. The reaction mixture was then refluxed for 1 h and then cooled to room temperature. The clear solution was poured into 100 mL of water, basified with 40% NaOH and extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate filtered. The filtrate was concentrated in vacuo to give 8.2 g (83%) of product as a brown oil which solidified upon standing, mp: 36-37 C.

With the rapid development of chemical substances, we look forward to future research findings about 6313-54-8.

Reference:
Patent; Pharmacia Corporation; US6509361; (2003); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 53234-55-2, 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. 53234-55-2, name is 5-Cyanopicolinic acid, molecular formula is C7H4N2O2, 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 5-cyanopicolinic acid (1 g, 6.75 mmol) in dry THF (10 mL) at -15C was added Et3N (0.68 g, 6.75 mmol), ethyl chloro formate (0.73 g, 6.75 mmol),and the mixture was stirred for 16 hours at -15C. Ether (15 mL), TMSCHN2 (1.54 g, 13.5 mmol) was added, and the mixture was stirred overnight while returning to room temperature. After completion, the reaction mixture was diluted with EtOAc (75 mL), washed with water (50 mL), brine (40 mL), dried over anhydrous Na2SO4, filtered andevaporated. The diazaketone was dissolved in dioxane:H20 (1:1) (10 mL), added AgCOOPh (cat), and the mixture was stirred at 100C for 16 hours. After completion, the reaction mixture was diluted with EtOAc (50 mL), acidified using iN HC1 and extracted using EtOAc (2 x 50 mL). The combined organic extracts were washed with water (50 mL), brine (50 mL), dried over anhydrous Na2SO4, filtered and evaporated. The crude compound was purified by triturating with ether (10 mL) and pentane (50mL) to afford 2-(5-cyanopyridin-2-yl) acetic acid (350 mg, 32 %) as yellow solid.

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 53234-55-2, 5-Cyanopicolinic acid.

Reference:
Patent; NUEVOLUTION A/S; SCHROeDER GLAD, Sanne; GROeN NOeRAGER, Niels; SARVARY, Ian; HAAHR GOULIAEV, Alex; TEUBER, Lene; STASI, Luigi, Piero; (244 pag.)WO2016/20288; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 154048-89-2 , The common heterocyclic compound, 154048-89-2, name is N-Boc-3-Amino-4-iodopyridine, molecular formula is C10H13IN2O2, 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.

Alternate Preparation: Tert-butyl 2-((benzyloxy)methyl)-lH-pyrrolo[2,3- c]pyridine-l-carboxylate was also prepared in an alternate preparation directly from tert-butyl tert-butyl (4-iodopyridin-3-yl)carbamate: In a sealed tube was added ((prop-2-yn-l-yloxy)methyl)benzene (104 mu, 0.750 mmol) and tert-butyl (4- iodopyridin-3-yl)carbamate (200 mg, 0.625 mmol) in DMF (625 mu). To this was added PdCl2(PPh3)2 (21.93 mg, 0.031 mmol), copper(I) iodide (11.90 mg, 0.062 mmol) and TEA (1742 mu, 12.50 mmol). This reaction was then degassed for 15 minutes and then allowed to stir at 80 C sealed. After 4 hours the reaction was complete. The reaction mixture was poured into ethyl acetate and saturated ammonium chloride. The organic was collected and washed several times with ammonium chloride. The organic was then purified on the biotage eluting in 10% ethyl acetate for 10 column volumes and then 10%-40% Ethyl acetate in hexanes over 10 column volumes. The product, tert-butyl 2-((benzyloxy)methyl)-lH- pyrrolo[2,3-c]pyridine-l-carboxylate (179 mg, 85% yield) was collected as a dark yellow oil. 1H NMR (400MHz, CHLOROFORM-d) delta = 9.58 – 9.20 (m, 1H), 8.70 – 8.42 (m, 1H), 7.54 – 7.34 (m, 6H), 6.78 (s, 1H), 4.98 (d, J=1.3 Hz, 2H), 4.73 (s, 2H), 1.69 (s, 9H).

The synthetic route of 154048-89-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; MCDONALD, Ivar, M.; OLSON, Richard, E.; MATE, Robert, A.; WO2015/191401; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 7295-76-3, 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. 7295-76-3, name is 3-Methoxypyridine, molecular formula is C6H7NO, 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.

General procedure: To a stirred, cooled (0 C) solution of 2,2,6,6-tetramethylpiperidine (0.25 mL, 1.5 mmol) in THF (2-3 mL) were successively added BuLi (about 1.6 M hexanes solution, 1.5 mmol) and, 5 min later, ZnCl2TMEDA[51] (0.13 g, 0.50 mmol). The mixture was stirred for 15 min at 0 C before introduction of the substrate (1.0 mmol) at 0-10 C. After 2 h at room temperature, a solution of I2 (0.38 g, 1.5 mmol) in THF (4 mL) was added. The mixture was stirred overnight before addition of an aqueous saturated solutionof Na2S2O3 (4 mL) and extraction with AcOEt (320 mL). The combined organic layers were dried over MgSO4, filtered and concentrated under reduced pressure. Purification by chromatographyon silica gel (the eluent is given in the product description) led to the compounds described below.

According to the analysis of related databases, 7295-76-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Hedidi, Madani; Bentabed-Ababsa, Ghenia; Derdour, Aicha; Halauko, Yury S.; Ivashkevich, Oleg A.; Matulis, Vadim E.; Chevallier, Floris; Roisnel, Thierry; Dorcet, Vincent; Mongin, Florence; Tetrahedron; vol. 72; 17; (2016); p. 2196 – 2205;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 571188-59-5, Adding some certain compound to certain chemical reactions, such as: 571188-59-5, name is tert-Butyl 4-(6-aminopyridin-3-yl)piperazine-1-carboxylate,molecular formula is C14H22N4O2, 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 571188-59-5.

To a solution of compound (11) (200.00 mg, 660.65 mumol, 1.00 eq) in dioxane (10.00 mL), compound (4) (220.67 mg, 792.79 mumol, 1.20 eq), Pd2(dba)3 (60.50 mg, 66.07 mumol, 0.10 eq) and Xantphos (76.45 mg, 132.13 mumol, 0.20 eq) and cesium carbonate (430.51 mg, 1.32 mmol, 2.00 eq) were added. The solution was heated to 110 C. under the protection of nitrogen gas and stirred for 16 hours. LCMS showed that the reaction was complete. The solution was cooled to 25 C., filtered and concentrated to obtain a crude product. The crude product was purified by preparative TLC (ethyl acetate:petroleum ether=1: 2) to obtain compound (12) (320.00 mg, 587.57 mumol, yield: 88.94%). LCMS (ESI) m/z: 545.3 (M+1).

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. 571188-59-5, tert-Butyl 4-(6-aminopyridin-3-yl)piperazine-1-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; CHIA TAI TIANQING PHARMACEUTICAL GROUP CO., LTD.; Ding, Charles Z.; Chen, Shuhui; Hu, Lihong; Xu, Zhaobing; Liu, Yingchun; Ren, Bingjie; Li, Weidong; Li, Zongbin; Zhao, Rui; Zhang, Xiquan; (21 pag.)US2019/194168; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 54923-31-8, Adding some certain compound to certain chemical reactions, such as: 54923-31-8, name is 5-Bromo-6-methylpyridin-2-ol,molecular formula is C6H6BrNO, 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 54923-31-8.

The 0.60g in the reference embodiment of preparing 7 mentioned in 7A, the 0.38g 3-bromo-6-hydroxy-2-methylpyridine, 0.55g the potassium carbonate and 8 ml of a mixture of acetonitrile in the accompanying 80 C heating and stirring of 4 hours. The water added to the reaction mixture and the mixture is extracted with chloroform. The organic layer with saturated aqueous salt solution washing, drying by anhydrous magnesium sulfate, and concentrated under reduced pressure, to obtain 0.80g of 1-[2-(5-bromo-6-methylpyridine-2-yloxymethyl)-3-methoxyphenyl]-4-methyl-1,4-dihydrotetrazole-5-one(called below 46A).

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. 54923-31-8, 5-Bromo-6-methylpyridin-2-ol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Sumitomo Chemical Co., Ltd.; Takayuki, Shiota; Masaki, Arimori; (241 pag.)CN105492432; (2016); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 230301-11-8 , The common heterocyclic compound, 230301-11-8, name is tert-Butyl 6,7-dihydro-1H-pyrazolo[4,3-c]pyridine-5(4H)-carboxylate, molecular formula is C11H17N3O2, 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.

A solution of 6-chloro-N-[4-ethyl-5-(4-fluorophenyl)-1H-pyrazol-3-yl]pyrimidin-4-amine (150 mg, 472 muetaiotaomicron) and tert-butyl 1,4,6,7-tetrahydro-5H-pyrazolo[4,3-c]pyridine-5-carboxylate (158 mg, 708 muiotaetaomicron, CAS 230301-11-8) in DMF (2.5 mL) was treated with caesium carbonate (461 mg, 1.42 mmol). The reaction mixture was stirred at 120C overnight and an additional night at 140C. The mixture was diluted with water, three times extracted with ethyl acetate. The combined organic phases were washed with water and brine, dried over sodium sulfate and the solvent was removed under reduced pressure. The crude product was purified by preparative reverse phase HPLC (method: column: Reprosil CI 8; 10 muiotaeta; 125×30 mm / flow: 50 ml/min / eluent: A = water (0,01% formic acid), B = acetonitrile / gradient: 0.00-5.00 min = 10% B, 6.50 min = 20% B, 17.0-19.75 min = 100% B, 19.75-23.00 min = 90% B). Subsequently the obtained regioisomeric mixture was separated using (HPLC) method to yield 13.2 mg (6% yield) of the desired product. LC-MS (method 9): Rt = 1.18 min; MS (ESIpos): m/z = 505 [M+H]+1H-NMR (400 MHz, DMSO-d6) delta [ppm] : -0.008 (3.40), 0.008 (2.05), 0.988 (1.10), 1.007 (2.36), 1.025 (1.06), 1.073 (0.74), 1.091 (1.48), 1.108 (0.71), 1.424 (16.00), 2.328 (0.41), 2.519 (2.00), 2.524 (1.93), 3.214 (0.83), 3.375 (0.71), 3.392 (0.70), 3.593 (0.62), 3.607 (1.06), 3.621 (0.50), 4.382 (1.39), 7.339 (0.53), 7.361 (1.03), 7.383 (0.62), 7.586 (0.61), 7.600 (0.70), 7.622 (0.53), 7.661 (1.24), 8.459 (0.81), 9.416 (0.72), 12.813 (0.67).

The synthetic route of 230301-11-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER AKTIENGESELLSCHAFT; BAYER PHARMA AKTIENGESELLSCHAFT; GIESE, Anja; KLAR, Juergen; EHRMANN, Alexander; WILLWACHER, Jens; ENGEL, David; DIESKAU, Andre Philippe; KAHNERT, Antje; GROMOV, Alexey; SCHMECK, Carsten; LINDNER, Niels; MUeLLER, Thomas; ANDREEVSKI, Anna Lena; DREHER, Jan; COLLINS, Karl; (861 pag.)WO2018/69222; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem