Pyridine-derivatives

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. 132606-40-7, name is 5-Bromo-2-chloro-6-methylpyridine, the common compound, a new synthetic route is introduced below. name: 5-Bromo-2-chloro-6-methylpyridine

To a stirred solution of 3-bromo-6-c oro-2-me1hylpyridine (105 g, 509 mmol) in CCI4 (2 L) was added N-bromosuccinimide (95 g, 534 mmol) followed by AIBN (8.35 g, 50.9 mmol). The reaction was brought to reflux for 24 hours and then cooled to r.t, filtered, and concentrated. Purification of the residue by flash chromatography on silica gel with 60% methylene chloride heptanes afforded 144.7 g of semi-pure product. Further purification by SFC on a Chiralpak AD-H column with 20% IPA/CO2 [the conditions of the preparative separation were as follows: column Chiralpak AD-H (2.1×25 cm, 5 um particle size) (Chiral Technologies, West Chester, PA, USA); mobile phase 20% 2-propanol/C02; elution mode isocratic pump-mixed; flow rate 50 mL rnin; pressure 100 bar.] gave 3-bromo-2-(bromomethyl)-6-cMoropyridine.LCMS – 285.7 (M+l)+ *H NMR (CDC13> 500 MHz) delta 7.81 (d, J= 8.4 Hz, 1H), 7.15 (d, J= 8.3 Hz, 1H), 4.63 (s, 2H).

The synthetic route of 132606-40-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; THOMPSON, Christopher, F.; SWEIS, Ramzi, F.; WO2011/28395; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 884495-39-0, 5-Bromo-2-methoxypyridin-3-amine, 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, HPLC of Formula: C6H7BrN2O, blongs to pyridine-derivatives compound. HPLC of Formula: C6H7BrN2O

A mixture of 2,4-difluorobenzenesulfonyl chloride (12.76 g, 60 mmol), pyridine (6 mL, 75 mmol), 5-bromo-2-methoxypyridin-3-amine 15a (10.15 g, 50 mmol), and DMAP (1.22 g, 10 mmol) in DCM (200 mL) was stirred at rt overnight. Water was added and the resulting mixture was extracted with DCM (200 mL×3). The combined organic layers were washed with water (200 mL×2) and brine (30 mL×2), dried over Na2SO4, filtered and concentrated. The residue was purified by column chromatography (silica gel, PE/EtOAc = 5:1) to afford 16a as a yellow solid (16.48 g, 87% yield). 1H NMR (400 MHz, DMSO-d6) delta 10.46 (s, 1H), 8.13 (d, J = 2.3 Hz, 1H), 7.84 – 7.70 (m, 2H), 7.64 – 7.51 (m, 1H), 7.23 (td, J = 8.5, 2.0 Hz, 1H), 3.61 (s, 3H). MS (ESI+) m/z 379.1 [M + H]+

At the same time, in my other blogs, there are other synthetic methods of this type of compound,884495-39-0, 5-Bromo-2-methoxypyridin-3-amine, and friends who are interested can also refer to it.

Reference:
Article; Lin, Songwen; Wang, Chunyang; Ji, Ming; Wu, Deyu; Lv, Yuanhao; Sheng, Li; Han, Fangbin; Dong, Yi; Zhang, Kehui; Yang, Yakun; Li, Yan; Chen, Xiaoguang; Xu, Heng; Bioorganic and Medicinal Chemistry; vol. 26; 3; (2018); p. 637 – 646;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 53939-30-3, 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.53939-30-3, name is 5-Bromo-2-chloropyridine, molecular formula is C5H3BrClN, molecular weight is 192.44, as common compound, the synthetic route is as follows.

EXAMPLE 2 N-(2,5-difluorobenzyl)-3-[4-(4-methylpiperazin-l-yl)phenyl][l ,2,4]triazolo[4,3-a]pyridin amine5 -Bromo-2-hydrazinylpyridine (2-2) Hydrazine (1,633 mL, 52.0 mmol) was mixed with a stirred, room temperature of 5-bromo-2- chloropyridine (2000 mg, 10.39 mmol) in dioxane (13 mL). The reaction mixture was stirred for 110 C for overnight. The reaction mixture was quenched with aqueous sodium hydrogen carbonate (saturated, 50 mL). The reaction mixture was extracted with EtOAc (3 x 30mL). The combined organic fractions were washed with brine (saturated, 40 mL), dried and filtered. The solvent was evaporated under reduced pressure to provide the title compound; MS (ES) m/z M calc’d; 188, found: 188.

The chemical industry reduces the impact on the environment during synthesis 53939-30-3, I believe this compound will play a more active role in future production and life.

Reference:
Patent; MERCK SHARP & DOHME CORP.; GREEN, Ahren; LI, Yiwei; STACHEL, Shawn; WO2012/125667; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1005291-43-9, 2-Bromo-5-fluoroisonicotinaldehyde, 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, category: pyridine-derivatives, blongs to pyridine-derivatives compound. category: pyridine-derivatives

2-Bromo-5-fluoroisonicotinaldehyde (2 g, 9.80 mmol) and hydroxylamine hydrochloride (1.022 g, 14.71 mmol) were dissolved in methanol (20 mL) and water (20 mL). The reaction mixture was heated at 60 C for 5 h. The reaction mixture was concentrated under reduced pressure. The residue was diluted with saturated aqueous sodium bicarbonate solution and was extracted with ethyl acetate. The ethyl acetate layer was dried over magnesium sulfate and concentrated under reduced pressure to obtain 2-bromo-5-fluoroisonicotinaldehyde oxime (1.8 g, 8.22 mmol, 84% yield) as an off-white solid which was carried forward without further purification. LCMS (ESI) m/e 219.0 [(M+H) +, calcd for C6H5BrFN20 219.0]; LC/MS retention time (method Al): tR = 1.63 min.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1005291-43-9, 2-Bromo-5-fluoroisonicotinaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; BRONSON, Joanne J.; CHEN, Ling; DITTA, Jonathan L.; DZIERBA, Carolyn Diane; JALAGAM, Prasada Rao; LUO, Guanglin; MACOR, John E.; MAISHAL, Tarun Kumar; NARA, Susheel Jethanand; RAJAMANI, Ramkumar; SISTLA, Ramesh Kumar; THANGAVEL, Soodamani; (485 pag.)WO2017/59085; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 72587-15-6, 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. 72587-15-6, name is 2-Chloro-3-nitro-5-(trifluoromethyl)pyridine, molecular formula is C6H2ClF3N2O2, 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.

Production Example 43(1) A mixture of 2-chloro-3-nitro-5- trifluoromethylpyridine (2.60 g), 2 , 2 , 2-trifluoroethylamine (0.79 g) , N, N-diisopropylethylamine (1.04 g) and N-methyl- 2-pyrrolidone (5 ml) was stirred at room temperature for 10 hours. To the reaction mixture was poured aqueous 10% citric acid solution, and then the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over sodium sulfate, and concentrated under reduced pressure to give ( 3-nitro-5-trifluoromethylpyridin- 2-yl) – (2, 2, 2-trifluoroethyl) amine (1.83 g) . ( 3-nit o-5-trifluoromethylpyridin-2-yl ) – ( 2 , 2 , 2- trifluoroeth l ) amine 1H-N R (CDCI3) delta: 8.72 (lH,d), 8.68 (lH,d), 8.59 (lH,brs), 4.54- .41 (2H,m) .

According to the analysis of related databases, 72587-15-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SUMITOMO CHEMICAL COMPANY, LIMITED; TAKAHASHI, Masaki; TANABE, Takamasa; ITO, Mai; NOKURA, Yoshihiko; IWATA, Atsushi; WO2013/18928; (2013); 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. 717843-48-6, name is 3-Bromo-6-methylpicolinonitrile. This compound has unique chemical properties. The synthetic route is as follows. HPLC of Formula: C7H5BrN2

Example 176 (7bR,11aS)-N-(2-Cyano-6-methyl-3-pyridinyl)-1,2,7b,8,9,10,11,11a-octahydro-4H-[1,4]oxazepino[6,5,4-hi]pyrido[4,3-b]indole-6-amine, bis hydrochloride salt A solution of tert-butyl (7bR,11aS)-6-amino-1,2,7b,10,11,11a-hexahydro-4H-[1,4]oxazepino[6,5,4-hi]pyrido[4,3-b]indole-9(8H)-carboxylate from Example 56, Part B (300 mg, 0.89 mmol), 2-cyano-3-bromo-6-methylpyridine (200 mg, 1.02 mmol) and cesium carbonate (565 mg, 1.73 mmol) in anhydrous toluene (10 mL) was stirred under an argon atmosphere in a sealable test tube. The mixture was degassed with argon. [1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium (II), complex with dichloromethane (35 mg, 0.043 mmol) was added and the reaction was sealed and heated at 160 C. in a microwave oven for 3600 sec. The reaction mixture was cooled, filtered through a pad of silica gel and concentrated in vacuo. Purification of the residue by flash column chromatography (silica gel, 10-50% EtOAc/hexanes) provided tert-butyl (7bR,11aS)-6-(2-cyano-6-methyl-3-pyridinyl)-amino-1,2,7b,10,11,11a-hexahydro-4H-[1,4]oxazepino[6,5,4-hi]pyrido[4,3-b]indole-9(8H)-carboxylate.

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, 717843-48-6, 3-Bromo-6-methylpicolinonitrile.

Reference:
Patent; Robichaud, Albert J.; Fevig, John M.; Mitchell, Ian S.; Lee, Taekyu; Chen, Wenting; Cacciola, Joseph; US2004/186094; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 5470-70-2, 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 5470-70-2, name is Methyl 6-methylnicotinate. This compound has unique chemical properties. The synthetic route is as follows.

Production Example 1-1: Methyl 6-bromomethylnicotinate To a solution of methyl 6-methylnicotinate (50g, 331mmol) in carbon tetrachloride (625mL), was added N-bromosuccinimide (59g, 331mmol). Further 1.0g of benzoyl peroxide was added, the mixture was reacted at a temperature from 40 to 50C for 24 hours with irradiation of light from a projector. After the reaction mixture was cooled, the precipitated crystals were separated by filtration. The filtrate was washed with an aqueous solution containing sodium hydrogencarbonate, and concentrated. The residue obtained by the concentration was purified by silica gel column chromatography, thereby to yield 37g of the target compound. 1H-NMR (CDCl3, 300MHz): delta 3.96(3H, s, OCH3), 4.58(2H, s, CH2Br), 7.54(1H, d, Py), 8.30(1H, dd, Py), 9.17(1H, d, Py)

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 5470-70-2, Methyl 6-methylnicotinate.

Reference:
Patent; KABUSHIKI KAISHA NARD KENKYUSHO; EP1455189; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1681-37-4 ,Some common heterocyclic compound, 1681-37-4, molecular formula is C5H5N3O2, 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 4-amino-3-nitropyridine (2.0 mmol) in DMF (10 mL), NaH (2.2 mmol) was addedslowly, the mixture was stirred at room temperature for 30 min. Then ethyl iodine (2.0 mmol) wasadded slowly into the mixture until the reaction is finished monitored by TLC. Then the solvent wasevaporated and the residue was purified by silica gel chromatography by DCM/MeOH system toafford 4-ethylamino-3-nitropydine.To a solution of 4-ethylamino-3-nitropydine (1.0 mmol) in EtOH (10 mL), 10% Pd/C was added.Then the mixture was reduced by catalytic hydrogenation. Until the completion of the reaction,the Pd/C was filtered and the solvent was evaporated. The product was used in the next step withoutfurther purification.The solution of substituted 4-ethylamino-3-aminopydine (0.5 mmol), benzaldehyde (0.5 mmol)with sodium pyrosulfite (0.5 mmol) was stirred in DMF (8 mL) under 120 C overnight. On completionof the reaction, the solvent was evaporated and the residue was purified by silica gel chromatographyby DCM/MeOH system to afford the final product. If necessary, the crude product could berecrystallized in DCM to afford pure compound [31].

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. 1681-37-4, 4-Amino-3-nitropyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Pan, Liangkun; Hang, Nan; Zhang, Chao; Chen, Yu; Li, Shuchun; Sun, Yang; Li, Zhongjun; Meng, Xiangbao; Molecules; vol. 22; 2; (2017);,
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. 65-22-5, name is 3-Hydroxy-5-(hydroxymethyl)-2-methylisonicotinaldehyde hydrochloride, molecular formula is C8H10ClNO3, 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: 3-Hydroxy-5-(hydroxymethyl)-2-methylisonicotinaldehyde hydrochloride

H2L2 was prepared by stirring 2-aminophenol (0.218 g, 2.00 mmol) dissolved in 6 mL of methanol/KOH pH ca. 9.0 and pyridoxal hydrochloride (0.407 g, 2.00 mmol) in 8 mL methanol, at room temperature for 3 h. After cooling the mixture was kept at 4 C overnight and the orange solid was filtered, washed with water, cold methanol and diethyl ether and dried under vacuum. Yield: 85%, 0.390 g. MM (C14H14N2O3) = 258.3 g/mol. Elemental Analysis: Calc. forC14H14N2O3: C, 65.11; H, 5.46; N, 10.85; Found: C, 64.9; H, 5.7; N,10.7. ESI-MS: m/z [Found (Calcd)]: 259.15 (259.3) (100%) [L+H]+;257.11 (257.29) (100%) [L-H]-. UV-Vis in dmso, lambdamax/nm (epsilon/M-1cm-1): 295 (8282), 360 (11601), 463 (421); 1H NMR (dmso-d6, delta/ppm): 2.55 (s, 3H, H17); 4.89 (s, 2H, H18); 6.97 (t, 1H, H2); 7.07 (d, 1H,H6); 7.28 (t, 1H, H1); 7.69 (d, 1H, H3); 7.98 (s, 1H, H12); 9.30 (s, 1H,H9); 5.63 (s, 1H, R-OH) and 10.45 (s, 1H, Ar-OH). 13C NMR (dmso-d6,delta/ppm): 16.15 (C17); 57.83 (C18); 116.82 (C6); 119.64 (C2); 119.73(C3); 121.82 (C11); 129.43 (C12); 130.45 (C1); 131.30 (C4); 136.82(C10); 147.13 (C14); 151.98 (C15); 156.28 (C9) and 157.82 (C5).LogP = 2.21 [24].

With the rapid development of chemical substances, we look forward to future research findings about 65-22-5.

Reference:
Article; Cavaco, Isabel; Correia, Isabel; Costa Pessoa, Joao; Marques, Fernanda; Nunes, Patrique; Inorganica Chimica Acta; vol. 507; (2020);,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 189278-27-1, 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 189278-27-1, name is 2-Bromo-6-(trifluoromethyl)pyridine. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 2-bromo-6-(trifluoromethyl)pyridine (200 mg, 0.885 mmol) in a solvent mixture of toluene (1.5 ml)/water (1.5 ml)/ethanol (0.7 ml) was added 3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)pyridine (200 mg, 0.738 mmol), cesium carbonate (601 mg, 1.844 mmol) and 1,1′-bis(diphenylphosphino)ferrocenepalladium(II) dichloride (30.3 mg, 0.037 mmol). The reaction mixture was heated in a benchtop microwave at 120 C. for 30 min. The reaction mixture was diluted with water and extracted with EtOAc. The organics were dried with MgSO4, filtered and then concentrated in vacuo. The residue was purified by column chromatography, eluting with 0-50% acetone in hexanes to afford 2-(1-(pyridin-3-yl)-1H-pyrazol-4-yl)-6-(trifluoromethyl)pyridine as a white solid (82 mg, 38.3%): mp 130-131 C.; 1H NMR (400 MHz, acetone-d6) delta 9.24 (d, J=2.4 Hz, 1H), 9.13 (d, J=0.5 Hz, 1H), 8.60 (dd, J=4.7, 1.4 Hz, 1H), 8.44 (s, 1H), 8.35 (ddd, J=8.3, 2.7, 1.5 Hz, 1H), 8.12 (qd, J=8.3, 4.7 Hz, 2H), 7.72 (dd, J=7.1, 1.5 Hz, 1H), 7.59 (ddd, J=8.3, 4.7, 0.7 Hz, 1H); EIMS m/z 290.

According to the analysis of related databases, 189278-27-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; DOW AGROSCIENCES LLC; Lowe, Christian T.; Trullinger, Tony K.; Hunter, Ricky; US2012/220453; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem