Tag: M.W:100-200

Application of 1462-86-8 ,Some common heterocyclic compound, 1462-86-8, molecular formula is C6H6N2O2, 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: Method B: To a solution of 3-aminopyridine-2-carboxylic acid (2.74 g, 20 mmol) in anhydrous DMF (100 mL) was added EDC (4.2 g, 22 mmol), HOBt (2.97 g, 22 mmol) and triethylamine (8.2 mL, 60 mmol). alpha-Amino acid methyl ester (22 mmol) was added, and the reaction mixture was stirred overnight. Water (100 mL) was added, and the mixture was extracted with methylene chloride (4 ¡Á 100 mL), dried over MgSO4 and concentrated. The compound was purified by silica gel chromatography to give the oil-like open product 6; this was then dissolved in THF (125 mL) under argon. Sodium hydride (0.93 g, 60% dispersion in oil, 26.8 mmol) was added, and the reaction mixture was stirred overnight. Water (5 mL) was carefully added, and the resulting white precipitate was collected. The precipitate was dissolved in ethyl acetate (200 mL), washed with water (50 mL) and brine (50 mL), dried over MgSO4 and concentrated to give product 8.

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. 1462-86-8, 3-Aminopicolinic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Article; El Bouakher, Abderrahman; Laborie, Helne; Aadil, Mina; El Hakmaoui, Ahmed; Lazar, Said; Akssira, Mohamed; Viaud-Massuard, Marie-Claude; Tetrahedron Letters; vol. 52; 39; (2011); p. 5077 – 5080;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 85838-94-4 ,Some common heterocyclic compound, 85838-94-4, molecular formula is C10H17NO2, 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.

tert-butyl 5,6-dihydropyridine-1(2H)-carboxylate (2) (1 mol)was added to a solution of potassium osmate (0.1 mol) and NMO(2 mol) in THF and H2O (4:1; 10 v). The reaction mixturewas stirredat RT for 16 h and a solution of saturated sodium metabisulfite (10v) was added to quench the excess oxidant. The reaction mixturewas diluted with water (40 v) and extracted with EtOAc (2 x 20 v).The combined organic layers were washed with saturated brinesolution, dried over Na2SO4 and evaporated under vacuo. Purificationwas done by flash column chromatography using EtOAc inhexane, afforded the desired product as a clear liquid in 88% yield.1H NMR (400 MHz, CDCl3): d 3.84 (br s, 1H), 3.75 (br s, 1H),3.56e3.50 (m, 2H), 3.41 (dd, J 13.2, 3.6 Hz, 1H), 3.28e3.22 (m, 1H),1.84e1.76 (m, 1H), 1.70e1.63 (m, 1H), 1.44 (s, 9H); 13C NMR(100 MHz, CDCl3): d 155.35, 79.96, 68.43, 67.91, 45.66, 40.17, 29.51,28.32; LC-MS (ESI) m/z Calcd. for C10H19NO4: 217.13, Found: 216.06[M H]-

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,85838-94-4, its application will become more common.

Reference:
Article; Kasturi, Siva Prasad; Surarapu, Sujatha; Uppalanchi, Srinivas; Dwivedi, Shubham; Yogeeswari, Perumal; Sigalapalli, Dilep Kumar; Bathini, Nagendra Babu; Ethiraj, Krishna S.; Anireddy, Jaya Shree; European Journal of Medicinal Chemistry; vol. 150; (2018); p. 39 – 52;,
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Pyridine | C5H5N – PubChem

Synthetic Route of 29681-43-4, Adding some certain compound to certain chemical reactions, such as: 29681-43-4, name is Methyl 4-methoxypyridine-2-carboxylate,molecular formula is C8H9NO3, 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 29681-43-4.

A solution of lithium aluminium hydride (1M in diethyl ether, 16 ml) was added dropwise to a stirred mixture of methyl 4-methoxypyridine-2-carboxylate (2.7 g) and diethyl ether (50 ml). The resultant mixture was heated to reflux for 1 hour. The mixture was treated with potassium sodium tartrate tetrahydrate and extracted with ethyl acetate. The organic phase was dried (MgSO4) and evaporated. The residue was purified by column chromatography using increasingly polar mixtures of methylene chloride and methanol as eluent to give 4-methoxypyrid-2-ylmethanol (0.8 g); NMR Spectrum: 3.62 (s, 3H), 4.51 (d, 2H), 5,34 (broad t, 1H), 6.8 (m, 1H), 6.99 (d, 1H), 8.27 (d, 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. 29681-43-4, Methyl 4-methoxypyridine-2-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Zeneca Limited; US5821246; (1998); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 74115-13-2, 5-Bromo-3-pyridinol, 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, name: 5-Bromo-3-pyridinol, blongs to pyridine-derivatives compound. name: 5-Bromo-3-pyridinol

j0651j To a solution of 5-bromopyridin-3-ol (XLIX) (174 mg, 1.0 mmol) in DMF (3 mL) was added potassium carbonate (415 mg, 3.0 mmol). The slurry was heated at 90C for 1 h and then cooled to 25C. The (bromomethyl)benzene (LIII) (171 mg, 1.0 mmol) was added and the mixture was stirred at 25C overnight. The reaction was worked-up using a saturated sodium bicarbonate and EtOAc extraction. The product was purified by ISCO column (40-100% EtOAchexanes). The 3-(benzyloxy)-5-bromopyridine (LIV) (105 mg, 0.398 mmol, 39.8 % yield) was obtained as yellow oil. ESIMS found for C,2H,oBrNO mlz 266.1 (M+H).

The synthetic route of 74115-13-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SAMUMED, LLC.; KC, Sunil Kumar; WALLACE, David Mark; CAO, Jianguo; CHIRUTA, Chandramouli; MARAKOVITS, Joseph Timothy; BOLLU, Venkataiah; HOOD, John; (300 pag.)WO2017/23972; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 71935-32-5, 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. 71935-32-5, name is 4-(Hydroxymethyl)picolinonitrile. A new synthetic method of this compound is introduced below.

Step 2, Method 6: 4-Formylpyridine-2-carbonitrile [0166] 4-(Hydroxymethyl)pyridine-2-carbonitrile (120 mg, 0.895 mmol) was dissolved in dichloromethane (3 mL) with stirring at room temperature. 1, 1, 1- Triacetoxy-l, l-dihydro-l,2-benziodoxol-3(lH)-one (417 mg, 0.984 mmol) was added and the reaction mixture stirred at room temperature for 4 hours. Dichloromethane (5 mL) and saturated aqueous sodium bicarbonate (8 mL) were added and thelayers separated. The organic layer was washed with water (8 mL) and brine (8 mL), dried over magnesium sulphate, filtered and concentrated to give the title compound 123 mg (60% purity, 60% yield) as a pale yellow solid which was used in the next step without further purification.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,71935-32-5, 4-(Hydroxymethyl)picolinonitrile, and friends who are interested can also refer to it.

Reference:
Patent; CHDI FOUNDATION, INC.; DOMINGUEZ, Celia; WITYAK, John; BARD, Jonathan; BROWN, Christopher, John; PRIME, Michael, Edward; WEDDELL, Derek, Alexander; WALTER, Daryl, Simon; GILES, Paul, Richard; WIGGINTON, Ian, James; TAYLOR, Malcolm, George; GALAN, Sebastien, Rene, Gabriel; JOHNSON, Peter, David; KRUeLLE, Thomas, Martin; MORAO, Inaki; CLARK-FREW, Daniel; SCHAERTL, Sabine; HERRMANN, Frank; GRIMM, Steffen, Kaspar; KAHMANN, Jan, Dirk; SCHEICH, Christoph; (120 pag.)WO2016/33460; (2016); 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.871836-51-0, name is 4-Chloro-1H-pyrazolo[4,3-c]pyridine, molecular formula is C6H4ClN3, molecular weight is 153.5691, as common compound, the synthetic route is as follows.Formula: C6H4ClN3

To a solution of 4-chloro-1H-pyrazolo[4,3-c]pyridine (3.7 g) in THF (40 mL) was added NaH (1.93 g, 60% purity) at 0C. After stirring for 1 hour, benzyl bromide (3.15 mL) was added, and the mixture was stirred at 15C for 15 hours. The reaction mixture was quenched with water and extracted ethyl acetate. The organic layers were washed with brine, dried over Na2SO4, concentrated, and purified by silica gel chromatography (petroleum ether : ethyl acetate = 50 : 1 to 20 : 1) to give the target compound (3.1 g) as a solid. (2045) [00999] MS: (M+H+): 244.0

At the same time, in my other blogs, there are other synthetic methods of this type of compound,871836-51-0, 4-Chloro-1H-pyrazolo[4,3-c]pyridine, and friends who are interested can also refer to it.

Reference:
Patent; HLA, Timothy; JILISHITZ, Irina; MEINKE, Peter; STAMFORD, Andrew; FOLEY, Michael; SATO, Ayumu; WADA, Yasufimi; FUKASE, Yoshiyuki; KINA, Asato; TAKAHAGI, Hiroki; IGAWA, Hideyuki; POLVINO, William J.; (0 pag.)WO2019/173790; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 58481-04-2, 2-Chloroisonicotinohydrazide, 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, Safety of 2-Chloroisonicotinohydrazide, blongs to pyridine-derivatives compound. Safety of 2-Chloroisonicotinohydrazide

EXAMPLE 3; This Example illustrates the preparation of compound ni. 3,2-chloroisonicotinic acid [1′- [trans-3- (4-chlorophenyl) allyl] spiro [indan-1-ylidene-3, 4′-piperidine]] hydrazide; To a solution of l’- [trayzs-3- (4-chlorophenyl) allyl] spiro [indan-1-one-3, 4′-piperidine] (example 1, step B) (20 mg) in ethanol (3 ml) was added 2-chloro-isonicotinic acid hydrazide (15 mg) and one drop of sulphuric acid. The reaction mixture was refluxed for 12 hours and concentrated in vacuo. The residue was dissolved in dichloromethane, washed with saturated aqueous sodium bicarbonate, dried (sodium sulphate) and concentrated in vacuo. The solid residue was purified by preparative HPLC to give 22 mg of 2- chloroisonicotinic acid [1′- [trans-3- (4-chlorophenyl) allyl] spiro [indan-1-ylidene-3, 4′- piperidine] ] hydrazide; M. p. 240C. IH NMR (400 MHz, CDCl3) 1.5 (m, 2H), 2.15 (m, 4H), 2.70 (s, 2H), 3.03 (m, 2H), 3.21 (m, 2H), 6.26 (dt, J = 15.8 Hz, 5.8 Hz, 1H), 6.45 (d, J = 15.8Hz, 1H), 7.1-7. 9 (m, 10H) ; 8.50 (d, J = 4.7 Hz, 1H), 9.42 (br s, 1H) ; MS (ES+) 505/507 (M+H+).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,58481-04-2, 2-Chloroisonicotinohydrazide, and friends who are interested can also refer to it.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; WO2005/58836; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 86873-60-1, 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. 86873-60-1, name is 5-Chloro-2-picolinic acid. A new synthetic method of this compound is introduced below.

5-Chloro-2-pyridine carboxylic acid (48.5 mg, 0.31 mmol) was added to a stirred sol. of 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (155 mg, 0.34 mmol) in MeOH (10 mL). After 5 mm, intermediate compound 1-16 (100 mg, 0.28 mmol) in MeOH (5 mL) was added at 0 C. The mixture was stirred at rt for 16 h. Themixture was treated with sat. aq. Na2CO3 sol. and extracted with DCM. The organic phase was separated, dried (MgSO4), filtered and the solvents evaporated in vacuo. The crude product was purified by flash column chromatography (silica; DCM-MeOH (10:1(25% NH3), v/v) in DCM 0/100 to 40/60). The desired fractions were collected and the solvents evaporated in vacuo. The solid was triturated with DIPE and filtered to yield compound 8 as a solid (69 mg, 50%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,86873-60-1, 5-Chloro-2-picolinic acid, and friends who are interested can also refer to it.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; OEHLRICH, Daniel; GIJSEN, Henricus, Jacobus, Maria; WO2014/198851; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 614750-81-1, 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.614750-81-1, name is [1,2,4]Triazolo[1,5-a]pyridine-6-carbaldehyde, molecular formula is C7H5N3O, molecular weight is 147.13, as common compound, the synthetic route is as follows.

Step 4: 1 – [1 ,2,4] Triazolo [1 ,5-a] pyridin-6-yl-3-(8-trimethylsiIanyloxy-l ,4-dioxa- spiro[4.5]dec-8-yl)-prop-2-yn-l-ol; [00166] To a solution of N,N-diisopropylamine (4.6 mL, 0.033 mol; Aldrich) in anhydrous THF (10OmL, Acros) was added dropwise 1.6 M n-butyllithium in hexane (19.0 mL; Aldrich) at -78 ¡ãC and the mixture stirred for Ih. To the above solution was added dropwise a solution of (8-ethynyl-l,4-dioxa-spiro[4.5]dec-8-yloxy)-trimethylsilane (6.5 g, 0.026 mol) in anhydrous THF (5OmL, Acros) at -78 ¡ãC and the mixture stirred for Ih. To the above solution was added dropwise a solution of [l,2,4]triazolo[l,5-a]pyridine-6-carbaldehyde (4.1 g, 0.028 mol) in anhydrous THF (15OmL, Acros) at -78 ¡ãC and the mixture stirred for Ih. The mixture was allowed to warm to room temperature then quenched with water and extracted with ethyl acetate (3x). The combined organic phases were washed with saturated ammonium chloride dried over MgSO4, concentrated and the residue purified on CombiFlash silica gel column with 0-100percent ethyl acetate in methylene chloride to give the desired product (2.4g, 22percent) and the desilyated product (4.2g, 50percent). ES+/330.42

The chemical industry reduces the impact on the environment during synthesis 614750-81-1, I believe this compound will play a more active role in future production and life.

Reference:
Patent; BIOGEN IDEC MA INC.; WO2008/94574; (2008); A2;,
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. 143468-13-7, name is 6-Bromo-1H-pyrrolo[2,3-b]pyridine, molecular formula is C7H5BrN2, 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. Safety of 6-Bromo-1H-pyrrolo[2,3-b]pyridine

General procedure: To a degassed 3.5:1 mixture of dimethoxyethane and water (2mL), compound 5 (0.5mmol), the appropriate boronic acid (1mmol), PdCl2(dppf)CH2Cl2 (0.025mmol) and sodium bicarbonate (1.5mmol) were added under nitrogen. The mixture was heated for 1-4h. The layers were separated and the organic phase was evaporated. Purification by flash chromatography gave the desired compounds. Following this procedure compounds 1m-n, 6b-e, 6g-h, 6j, 6l-m, 11, 15 were prepared.

With the rapid development of chemical substances, we look forward to future research findings about 143468-13-7.

Reference:
Article; Cincinelli, Raffaella; Musso, Loana; Merlini, Lucio; Giannini, Giuseppe; Vesci, Loredana; Milazzo, Ferdinando M.; Carenini, Nives; Perego, Paola; Penco, Sergio; Artali, Roberto; Zunino, Franco; Pisano, Claudio; Dallavalle, Sabrina; Bioorganic and Medicinal Chemistry; vol. 22; 3; (2014); p. 1089 – 1103;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem