Day: June 10, 2021

Reference of 1256823-65-0 ,Some common heterocyclic compound, 1256823-65-0, molecular formula is C6H2BrClN2, 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 mixture of 5-bromo-6-chloropicolinonitrile (5 g, 22.99 mmol) and tributyl (1-ethoxyvinyl) stannane (8.30 g, 22.99 mmol) in toluene (10 mL) was added tetrakis (triphenyl-phosphine) palladium (0) (0.531 g, 0.460 mmol) and the mixture was stirred at 110 under N2for 16h. The mixture was cooled to rt and conc. HCl (1.888 mL, 22.99 mmol) was added to the mixture. The grey mixture was stirred at 25 for 1h. The mixture was diluted with water (10 mL) and extracted with ethyl acetate (15 mL x 3) . The combined organic layers were washed with brine (10 mL x 2) , dried over sodium sulfate, filtered and the filtrate was concentrated in vacuum. The residue was purified by column chromatography (SiO2, petroleum ether: ethyl acetate from 10: 1 to 3: 1) to give the title compound.1HNMR (CDCl3, 400 MHz) delta: 7.99 (d, J 8.0 Hz, 1H) , 7.73 (d, J 7.6 Hz, 1H) , 2.72 (s, 3H) .

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. 1256823-65-0, 5-Bromo-6-chloropicolinonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MSD R&D (CHINA) CO., LTD.; BAO, Jianming; HENDERSON, Timothy J.; LO, Michael Man-chu; MAZZOLA, JR., Robert D.; RUDD, Michael T.; TELLERS, David M.; TONG, Ling; LI, Chunsing; NA, Meng; (144 pag.)WO2019/238; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 83004-10-8 ,Some common heterocyclic compound, 83004-10-8, molecular formula is C6H5Br2N, 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.

Synthesis of N-((6-Bromopyridin-2-yI)methyl)-N-(1-isopropylpiperidin-4-yI)-4-(4-(trifluoromethyl)phenyl)pyrimidin-2-amineTo an ice-cooled solution of (1 -isopropyl-piperid in-4-yl)-[4-(4-trifluoromethyl-phenyl)-pyrimidin-2-yl]-amine (1.00 g, 2.74 mmol, 1.0 eq.) in DMF (15 mL), sodium hydride 60%dispersion in mineral oil (154 mg, 3.84 mmol, 1.4 eq.) was added. The resulting orange mixture was stirred at r.t. for 2 hours. Then a solution of 2-bromo-6-(bromomethyl)pyridine (757 mg, 3.02 mmol, 1.1 eq.) in DMF (5 mL) was added dropwise and the mixture was stirred at 60 C for 18 hours. The mixture was cooled to 0 C and sodium hydride 60%dispersion in mineral oil (77 mg, 1.92 mmol, 0.7 eq.) was added. The resulting orange mixture was stirred at r.t. for 2 hours. Then a solution of 2-bromo-6-(bromomethyl)pyridine (378 mg, 1.51 mmol, 0.55 eq.) in DMF (2 mL) was added dropwise and the mixture was stirred at 60 C 4 hours. The reaction mixture was quenched with sat. aq. Na2CO3 solution. The mixture was extracted with DCM. The comb. org. phases were washed with water, sat.aq. NaCI soln., dried over MgSO4, and concentrated in vacuo. The residue was purified by flashmaster (column: 50 g, flow: 40 mL/min, 35 fractions of 45 mL, Hept/AcOEt-NEt3 (10% NEt3) 95:5 to Hept/AcOEt-NEt3 (10% NEt3) 1:1) to afford the title compound as an orange oil.LC-MS 4: tR = 0.82 mm; [M+H] = 534.2

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. 83004-10-8, 2-Bromo-6-(bromomethyl)pyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ACTELION PHARMACEUTICALS LTD; AISSAOUI, Hamed; BOSS, Christoph; CIANA, Claire-Lise; KIMMERLIN, Thierry; SIEGRIST, Romain; WO2015/28989; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 866546-07-8 ,Some common heterocyclic compound, 866546-07-8, molecular formula is C7H5ClN2, 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.

Step 4 ~~ Preparation of[3-benzyloxy-2-cyclopropylmethoxy-phenyl]-(5-chloro-lH-pyrrolo[2,3- b]pyridin-3-yl)-methanol (131):[0206] A mixture of 5-chloro-lH-Pyrrolo[2,3-6]pyridine (4, 0.68 g, 4.46 mmol), 3-benzyloxy-2- cyclopropylmethoxy-benzaldehyde (130, 1.2 g, 4.25 mmol), and potassium hydroxide (0.68 g, 1 1 mmol) in methanol (50 mL) was stirred at room temperature for 4 days. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was collected, washed with brine, and dried over sodium sulfate. After removal of solvent, the residue was purified by silica gel column chromatography eluting with ethyl acetate in hexane to provide compound as a white solid (131, 0.99g, 54%). MS(ESI) [M+H’]’ = 435.21.

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. 866546-07-8, 5-Chloro-1H-pyrrolo[2,3-b]pyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PLEXXIKON, INC.; WO2008/80001; (2008); A2;,
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 14294-11-2, name is 1-(Pyridin-2-yl)thiourea. This compound has unique chemical properties. The synthetic route is as follows. Product Details of 14294-11-2

According to Scheme 3 Step 4: A solution of 2-bromo-1-(1-(4-methoxybenzyl)-1H-pyrazol-4-yl)propan-1-one (23.8 mmol, 7.70 g) and of 1-(pyridin-2-yl)thiourea (26.2 mmol, 4.02 g) in EtOH (200 mL) was stirred under reflux overnight. The reaction was quenched with water (200 mL) and the aqueous phase was extracted with DCM. The organic phase was dried over MgSO4, was filtered and was concentrated to yield a brown solid. The resulting crude product was purified by flash chromatography over silica gel using DCM/AcOEt (98:2) as eluent to yield after evaporation 4-(1-(4-methoxybenzyl)-1H-pyrazol-4-yl)-5-methyl-N-(pyridin-2-yl)thiazol-2-amine (20.7 mmol, 7.80 g, 87%) as a beige solid.LC (Zorbax SB-C18, 3.5 mum, 4.6×50 mm Column): RT=2.29 min; MS m/z ES+=378.

With the rapid development of chemical substances, we look forward to future research findings about 14294-11-2.

Reference:
Patent; Bolea, Christelle; Calanire, Sylvain; US2010/144756; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 754230-78-9 ,Some common heterocyclic compound, 754230-78-9, molecular formula is C12H11BrN2O, 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.

Example 85A Ethyl 8-(benzyloxy)-6-bromo-2-methylimidazo[1,2-a]pyridine-3-carboxylate Under argon, 200 g (0.72 mol) of 3-(benzyloxy)-5-bromopyridine-2-amine Example 84A, 590 g (3.58 mol) of ethyl 2-chloroacetoacetate and 436 g 3 A molecular sieve were suspended in 6 l of ethanol and boiled at reflux for 72 h. The reaction mixture was filtered off through kieselguhr and concentrated. The residue was purified by silica gel chromatography (petroleum ether:ethyl acetate 9:1, then 6:4) and the product fractions were concentrated. This gave 221 g (79% of theory) of the target compound. LC-MS (Method 17): Rt=1.31 min MS (ESpos): m/z=389 (M+H)+ 1H NMR (400 MHz, DMSO-d6): delta=1.36 (t, 3H), 2.58 (s, 3H), 4.32-4.41 (m, 2H), 5.33 (s, 2H), 7.28-7.32 (m, 1H), 7.36-7.47 (m, 3H), 7.49-7.54 (m, 2H), 8.98 (d, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,754230-78-9, its application will become more common.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; VAKALOPOULOS, Alexandros; HARTUNG, Ingo; FOLLMANN, Markus; JAUTELAT, Rolf; STRAUB, Alexander; HAssFELD, Jorma; LINDNER, Niels; SCHNEIDER, Dirk; WUNDER, Frank; STASCH, Johannes-Peter; REDLICH, Gorden; LI, Volkhart Min-Jian; BECKER-PELSTER, Eva Maria; KNORR, Andreas; US2014/128386; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 34160-40-2, name is 6-Bromo-2-pyridinecarboxaldehyde. This compound has unique chemical properties. The synthetic route is as follows. name: 6-Bromo-2-pyridinecarboxaldehyde

Step 1: Synthesis of 2-bromo-6-(difluoromethyl)pyridine (0396) 3.81 g (23.6 mmol) of (diethylamino)sulfur trifluoride were added with ice cooling to a mixed solution of 2.00 g (10.8 mmol) of 6-bromopicolinaldehyde and 40 ml methylene chloride. After completion of the addition, said reaction mixture liquid was stirred for 2 hours with ice cooling. After completion of the stirring, the reaction was stopped by addition of 30 ml of saturated aqueous sodium hydrogen carbonate solution, and said reaction liquid was extracted with methylene chloride (2×30 ml). The organic layer obtained was washed with water, then dried with anhydrous sodium sulfate, and the solvent distilled off under reduced pressure. The residue obtained was purified by silica gel chromatography (n-hexane:ethyl acetate=10:0 to 8:2), and 1.87 g of the desired compound were obtained as a white solid. (0397) 1H-NMR (CDCl3, Me4Si, 300 MHz): delta 7.73-7.58 (m, 3H), 6.58 (t, 1H, J=56 Hz).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, 34160-40-2, 6-Bromo-2-pyridinecarboxaldehyde.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; NAKAYA, Yoshihiko; MASUZAWA, Yoshihide; FURUHASHI, Takamasa; MIYAKADO, Yuuki; HOTTA, Hiroyasu; INABA, Masamitsu; (76 pag.)US2016/221998; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 83004-14-2, 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. 83004-14-2, name is 2-Bromo-4-(bromomethyl)pyridine. A new synthetic method of this compound is introduced below.

Example 59 A mixture of 4-(4-chloro-2-fluoroanilino)-7-hydroxy-6-methoxyquinazoline (950 mg, 3 mmol), (prepared as described for the starting material in Example 24), 2-bromo-4-bromomethylpyridine (765 mg, 3 mmol) and potassium carbonate (2.38 g 17 mmol) in DMF (10 ml) was heated at 80 C. for 2 hours. The mixture was allowed to cool, poured into water and extracted with ethyl acetate. The combined extracts were dried (MgSO4) and the solvent removed by evaporation and azeotroped with toluene. The residue was triturated with ethyl acetate/hexane and the solid product collected by filtration, washed with ethyl acetate/hexane and dried to give 7-((2-bromo-4-pyridyl)methoxy)-4-(4-chloro-2-fluoroanilino)-6-methoxyquinazoline (647 mg, 44%). m.p. 210-212 C. 1 H NMR Spectrum: (DMSOd6) 3.98(s, 3H); 5.40(s, 2H); 7.25(s, 1H); 7.30(d, 1H); 7.50(s, 1H); 7.50(d, 1H); 7.55(m, 2H); 7.74(s, 1H); 7.86(s, 1H); 8.35(br s, 1H); 8.42(d, 1H); 9.56(s, 1H) MS – ESI: 489 [MH]+ Elemental analysis: Found C 52.0 H 3.2 N 11.2 C21 H15 N4 O2 BrClF Requires C 51.5 H 3.1 N 11.4%

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,83004-14-2, its application will become more common.

Reference:
Patent; Zeneca Limited; Zeneca Pharma S.A.,; US5962458; (1999); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 57266-69-0, 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. 57266-69-0, name is 3-Chloropicolinic acid. A new synthetic method of this compound is introduced below.

To a solution of 3-chloropicolinic acid (20.006 g, 126.98 mmol) in toluene (200 mL) was added thionyl chloride (23.2 mL, 37.8 g, 317 mmol, 2.5 equiv.) and a catalytic amount of DMF (10 drops) and the mixture was heated at reflux for 1 h. After cessation of the gas evolution, the mixture was cooled and all volatiles were removed in vacuum to obtain to obtain the title compound (24.38 g, quant.) as a crude product, 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,57266-69-0, 3-Chloropicolinic acid, and friends who are interested can also refer to it.

Reference:
Patent; BASF SE; DESHMUKH, Prashant; KOeRBER, Karsten; KAISER, Florian; KORDES, Markus; DICKHAUT, Joachim; NARINE, Arun; BANDUR, Nina Gertrud; VEITCH, Gemma; CULBERTSON, Deborah L.; NEESE, Paul; GUNJIMA, Koshi; WO2013/24006; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 35905-85-2, 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. 35905-85-2, name is 2-Bromonicotinic acid. A new synthetic method of this compound is introduced below.

Step 2: Methyl 2-bromonicotinate (G2); A solution of of CH2N2 (4 eq.) in Et2O (1 M) was added dropwise to a solution of 2- bromonicotinic acid in THF (0.5 M) at RT. The reaction mixture was stirred at room temperature overnight, then quenched by dropwise addition of AcOH (4 eq.). The organic phase was washed with water and brine and dried (MgSO4). Evaporation of the solvent yielded (75%) the title compound which was used in the next step without further purification. 1H NMR (300MHz, CDCl3, 300K) delta 8.47 (IH, dd, J= 4.8 Hz, 2.1 Hz), 8.07 (IH, dd, J= 7.8 Hz, 2.1 Hz), 7.35 (IH, dd, J= 7.5 Hz, 4.5 Hz), 3.93 (3H, s).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,35905-85-2, 2-Bromonicotinic acid, and friends who are interested can also refer to it.

Reference:
Patent; ISTITUTO DI RICERCHE DI BIOLOGIA MOLECOLARE P. ANGELETTI S.P.A.; WO2009/112832; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 72716-87-1 , The common heterocyclic compound, 72716-87-1, name is 2-Methoxyisonicotinaldehyde, molecular formula is C7H7NO2, 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.

Nitrosonitric acid (1 mL) was added dropwise to a solution of 2-methoxypyridine-4-formaldehyde (137 mg, 1.0 mmol) in trifluoroacetic anhydride (2 mL) at room temperature. The reaction mixture was stirred at 25 C for 3 days, and then was poured into ice-water mixture, followed by the addition of saturated sodium carbonate solution to adjust the pH value to exceed 10. The resulting mixture was extracted with ethyl acetate, and the organic layer was washed with brine, dried and concentrated. The resulting residue was dissolved in toluene (5 mL), and toluene-p-sulfonic acid (5 mg) and glycol (105 mg, 1.7 mmol) were added. The reaction mixture was heated to reflux and reacted overnight. After cooled, the mixture was washed with saturated sodium carbonate solution and brine, dried, and concentrated under vacuum. The resulting residue was dissolved in methanol (10 mL), added Pd/C catalyst (20 mg), and introduced into hydrogen gas. The reaction system was stirred for 2 h under 1 atm hydrogen, then filtered to remove the catalyst, and concentrated under vacuum to remove the solvent. The residue was purified by column chromatography to obtain the title compound (15 mg, 8 %). 1H NMR (DMSO-d6): delta 9.31 (1H, s), 8.56 (1H, s), 7.42 (1H, s), 7.34 (1H, s), 6.55 (1H, s), 5.43 (2H, s), 5.30 (2H, s), 4.02 (3H, s), 2.04-1.91 (2H, m), 0.90-0.85 (3H, m).

The synthetic route of 72716-87-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Li, Yuliang; WANG, Huting; ZHU, Yan; WANG, Zhe; ZHANG, Hui; ZHAO, Ruiyu; HUANG, Yuanyuan; WANG, He; PENG, Yong; LUO, Hong; XIAO, Dengming; CAO, Shousong; HAN, Yongxin; EP2862571; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem