Pyridine-derivatives

Adding a certain compound to certain chemical reactions, such as: 863704-60-3, 6-(4-Fluorophenyl)picolinic acid, 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, Quality Control of 6-(4-Fluorophenyl)picolinic acid, blongs to pyridine-derivatives compound. Quality Control of 6-(4-Fluorophenyl)picolinic acid

A mixture of picolinic acid derivative (1.0 g, 4.6 mmol), Na2HPO4 (1.2 g) and m-CPBA (1.1 g, 70% from Aldrich) in CH2ClCH2Cl (30 mL) was stirred at rt for 2 h. Additional Na2HPO4 (0.8 g) and m-CPBA (1.0 g) was added to the reaction mixture and it was stirred for 3 h at rt. Another Na2HPO4 (0.5 g) and m-CPBA (0.5 g) was added to the reaction mixture and it was stirred at rt overnight. CHCl3 (160 mL) and 2 N aq. HCl solution (50 mL) were added to the reation mixture and the organic layer was separated, dried over MgSO4 and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel eluting with EtOAc/MeOH/HOAc//700:240:60 to obtain the desired product which was contaminated with m-CPBA. This impure material was purified by preparative HPLC to obtain the desired product (175 mg, 16%) as a white solid. 1H NMR (DMF-d7) 8.45 (dd, 1H, J=8.3, 2.2 Hz), 8.15 (d, 1H, J=2.2 Hz), 8.13-8.00 (m, 4H), 7.45 (t, 2H, J=8.7 Hz).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,863704-60-3, 6-(4-Fluorophenyl)picolinic acid, and friends who are interested can also refer to it.

Reference:
Patent; Borzilleri, Robert M.; Cornelius, Lyndon A.M.; Schmidt, Robert J.; Schroeder, Gretchen M.; Kim, Kyoung S.; US2005/245530; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 884494-82-0, 5-Fluoro-2-methoxynicotinic acid, 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, 884494-82-0, blongs to pyridine-derivatives compound. Formula: C7H6FNO3

[0429] A solution of 2-(4-(4-fluorobenzd)piperazin-l-yl)-6-methylpyridin-3-arnine (72 mg, 0.240 rnmol), 5-fluoro-2-methoxynicotinic acid (123 mg, 0.719 mmol), HATU (273 mg, 0.719 mmol) and DIPEA (167 muEpsilon, 0,959 mmol) in DMF (1199 muEpsilon) was stirred on a hot plate at 80C overnight. The reaction mixture was filtered through a Millipore filter, diluted with DMF and MeOH and purified by HPLC (Sliimadzu) eluting with a gradient of ACN in water (basic mode) to give the title compound as a pale brown solid (64.6 mg, 59.4%). NMR (400 MHz, CDCb) delta ppm 2,46 (s, 3 H), 2.64 (br s, 4 H), 3.14 (br s, 4 H), 3,60 (br s, 2 H), 4.16 (s, 3 H), 6.91 (d, J=8,08 Hz, 1 H), 7.03 (t, /=8.59 Hz, 2 H), 7.32 (br s, 2 H), 8.17 (d, J=3.28 Hz, 1 H), 8.36 (dd, (1382) -8.08 Hz, 1 H), 10.31 (br s, 1 H); ESI-MS m/z j M H | ‘ 454.3. (1383) (1384) [0430] The preparation of Example 100 yielded the title compound as a des-methyl side product which was recovered as an orange solid (12.4 mg, 11.8%). NMR (400 MHz, CDCb) delta ppm 2.40 – 2.47 (m, 3 H), 2.82 (br s, 4 H), 3,27 (br s, 6 H), 6,89 id. ./ 8.08 Hz, 1 H), 7,03 (t, ./ 7.96 Hz, 2 H), 7.42 (br s, 2 H), 7,55 (br s, 1 H), 8,53 – 8.64 (m, 2 H), 11.69 – 11,88 (m, 1 H); ESI-MS m/z [M+H]” 440.3.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,884494-82-0, its application will become more common.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; GREEN, Jason; HOPKINS, Maria; JONES, Benjamin; KIRYANOV, Andre A.; KUEHLER, Jon; MONENSCHEIN, Holger; MURPHY, Sean; NIXEY, Thomas; SUN, Huikai; (300 pag.)WO2018/183145; (2018); 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.10167-97-2, name is 2-Amino-5-methoxypyridine, molecular formula is C6H8N2O, molecular weight is 124.1405, as common compound, the synthetic route is as follows.Formula: C6H8N2O

(a) 2-Amino-5-methoxypyridine (14.8 g, prepared by the method of J.G. Lombardino, J. Med. Chem., 1981, 24, 39) was dissolved in 60% hydrobromic acid (150 ml) and to the cooled (-10) stirred solution bromine (47.47 g) was added dropwise. To the resulting yellow suspension was added, dropwise, sodium nitrite (20.53 g) in water (40 ml), keeping the temperature below -5. The mixture was stirred to room temperature, and after 0.5 hour cooled to 0, and a solution of sodium hydroxide (120 g) in water (100 ml) was slowly added. The mixture was thoroughly extracted with ether, the combined ether extracts dried with anhydrous sodium sulphate, and evaporated. The residue was chromatographed on silica gel (150 g). Elution with dichloromethane gave a yellow oil (14.1 g, 63%) which was combined with a smaller batch (3.4 g) and distilled under reduced pressure to give 2-bromo-5-methoxypyridine (16.4 g). b.p. 76-78/0.6 torr.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,10167-97-2, 2-Amino-5-methoxypyridine, and friends who are interested can also refer to it.

Reference:
Patent; Smith Kline & French Laboratories Ltd.; US4766121; (1988); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 102074-19-1, 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.102074-19-1, name is (5-Methylpyridin-3-yl)methanol, molecular formula is C7H9NO, molecular weight is 123.15, as common compound, the synthetic route is as follows.

Step 2.; Alcohol (10 mmol) were refluxed in 10ml HBr (40% aq) for more than 5 hours, and monitored through TLC or LC-MS. After completed, mixture were heated in order to evaporator solvents (water and excess HBr) until the mixture became sticky. Cool the mixture, add acetone to the mixture, precipitated solid and filtered followed by drying. Yield was high to80%.

The chemical industry reduces the impact on the environment during synthesis 102074-19-1, I believe this compound will play a more active role in future production and life.

Reference:
Patent; ACEA BIOSCIENCES INC.; MAO, Long; ZHAO, Li; LIU, Jia; WANG, Xiaobo; XU, Xiao; WO2012/97196; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1156542-28-7 , The common heterocyclic compound, 1156542-28-7, name is 5-Chloro-4-(trifluoromethyl)picolinonitrile, molecular formula is C7H2ClF3N2, 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 7 ml of ethanol were added 0.61 g of sodium bicarbonate and 0.5 g of hydroxylamine hydrochloride, and the mixture was heated to reflux for 1 hour. After allowing to cool, 0.74 g of 5-chloro-4-trifluoromethylpyridine-2-carbonitrile was added at O0C, and the mixture was stirred for 5 hours, and concentrated. To the residue was added water, the resultant solution was extracted with ethyl acetate three times, and the organic layers were combined, washed with an aqueous saturated sodium chloride solution, dried with anhydrous magnesium sulfate, and concentrated. The residue was subjected to silica gel column chromatography to obtain 0.6 g of 5-chloro-4- trifluoromethylpyridine-2-carboxamide=oxime. 5-Chloro-4-trifluoromethylpyridine-2-carboxamide=oxime1H-NMR (DMSO-d6): 6.02 (s, 2H), 8.14 (s, IH), 8.93 (s, IH), 10.31 (s, IH)

The synthetic route of 1156542-28-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SUMITOMO CHEMICAL COMPANY, LIMITED; WO2009/66786; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 72587-18-9, 2-Chloro-5-(trifluoromethyl)pyridin-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, 72587-18-9, blongs to pyridine-derivatives compound. Product Details of 72587-18-9

A 1 00-mL round bottom flask equipped with a magnetic stirrer was charged with 2-chloro-5- (trifluoromethyl)pyridine-3 -amine (1.0 g, 5.1 mmol), CH2C12 (15 mL), TEA (1.42 ml, 10.2 mmol). The reaction mixture was cooled under ice-bath and chloroacetyl chloride (0.81 ml, 10.2 mmol) was slowly added. The reaction mixture was stirred at room temperature for 2 hours. The sovent was removed under vacuum. The residue was purified by column chromatography using 20% EtOAc/hexane to afford the desired product as off-white solid (1.22 g, 88% yield). ). ?H NMR (300 MHz, CDC13) & 9.05 (s, 2H), 8.44 (s, 1H), 4.27 (s, 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,72587-18-9, its application will become more common.

Reference:
Patent; RUTGERS, THE STATE UNIVERSITY OF NEW JERSEY; TAXIS PHARMACEUTICALS, INC.; LAVOIE, Edmond J.; PARHI, Ajit; PILCH, Daniel S.; ZHANG, Yongzheng; KAUL, Malvika; WO2014/74932; (2014); A1;,
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. 1357947-08-0, name is 5-Bromo-3-iodo-1H-pyrazolo[3,4-c]pyridine, molecular formula is C6H3BrIN3, 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. Formula: C6H3BrIN3

To a solution of 5-bromo-3-iodo-1H-pyrazolo[3,4-c]pyridine (1 equiv) in CH3CN (10 vol) was added tert-butyl 2-bromoacetate (1.1 equiv) and potassium carbonate (1.1 equiv). The mixturewas refluxed overnight under an atmosphere of argon. After cooling the reaction mixture to room temperature, the mixture was filtered through Celite and washed with CH3CN. The filtrate was concentrated under reduced pressure and the remaining residue was purified by column chromatography on silica gel (eluted with DCMIMeOH) to afford compound 104-S2.

With the rapid development of chemical substances, we look forward to future research findings about 1357947-08-0.

Reference:
Patent; ACHILLION PHARMACEUTICALS, INC.; WILES, Jason, Allan; PHADKE, Avinash, S.; DESHPANDE, Milind; AGARWAL, Atul; CHEN, Dawei; GADHACHANDA, Venkat, Rao; HASHIMOTO, Akihiro; PAIS, Godwin; WANG, Qiuping; WANG, Xiangzhu; BARRISH, Joel, Charles; GREENLEE, William; EASTMAN, Kyle, J.; (0 pag.)WO2018/160889; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1211517-76-8 ,Some common heterocyclic compound, 1211517-76-8, molecular formula is C6H5BrFN, 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 3 A mixture of the intermediate from step 2 (150 mg, 0.54 mmol) and K2CO3 (150 mg, 1.09 mmol,) in toluene (5 mL) was degassed with Ar for 30 min. 3-bromo-5-fluoro-4-methyl-pyridine (97 muL, 0.815 mmol), CuI (5 mg, 0.027 mmol) and N,N’-dimethylethylenediamine (10 muL, 0.092 mmol) were added to the RM and heated at 100 C. in a sealed tube for 16 h. The RM was concentrated under reduced pressure, diluted with water and extracted with EtOAc. The organic layer was dried and concentrated under reduced pressure to give the crude product which was purified by CC (SiO2; 1% MeOH in CH2Cl2) to yield the title compound (115 mg, 55%). LC-MS (Method 2): m/z [M+H]+=386.2 (MW calc. 385.39); Rt=0.66 min. 1H-NMR (DMSO-d6, 400 MHz), delta (ppm)=9.94 (s, 1H), 8.48 (s, 1H), 8.36 (s, 1H), 7.98 (s, 1H), 6.60 (s, 1H), 3.91 (s, 3H), 3.85 (s, 3H), 3.69 (s, 3H), 2.19 (d, 3H, J=0.88 Hz), 2.06 (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. 1211517-76-8, 3-Bromo-5-fluoro-4-methylpyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GRUeNENTHAL GMBH; VOSS, FELIX; NORDHOFF, SONJA; WACHTEN, SEBASTIAN; WELBERS, ANDRE; RITTER, STEFANIE; US2015/166505; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1256834-13-5 , The common heterocyclic compound, 1256834-13-5, name is 4-Bromo-6-chloronicotinic acid, molecular formula is C6H3BrClNO2, 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 6-bromo-4-chloronicotinic acid (3 g, 12.69 mmol) in DMF (42 mL) was added HATU (6.27 g, 16.49 mmol), (R)-4-amino-3-fluoro-2-methylbutan-2-ol hydrochloride (2.4 g, 15.23 mmol), and N,N-Diisopropylethylamine (5.62 ml, 32.26 mmol). The resulting solution was stirred at room temperature overnight and subsequently diluted with ethyl acetate. The organic solution was washed with saturated aqueous lithium chloride (3 times), then dried over Na^SCri. and then concentrated. The residue was purified by silica gel chromatography (eluent: EtO Ac/hexanes) to provide (R)-6-bromo-4-chloro-N-(2-fluoro-3-hydroxy-3- methylbutyl)nicotinamide.ES/MS: 341.1 (M+H+).

The synthetic route of 1256834-13-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GILEAD SCIENCES, INC.; AMMANN, Stephen; BACON, Elizabeth M.; BRIZGYS, Gediminas; CHIN, Elbert; CHOU, Chienhung; COTTELL, Jeromy J.; NDUKWE, Marilyn; TAYLOR, James G.; WRIGHT, Nathan E.; YANG, Zheng-Yu; ZIPFEL, Sheila M.; (138 pag.)WO2020/36979; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 4966-90-9 ,Some common heterocyclic compound, 4966-90-9, molecular formula is C6H6N2O4, 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.

(1)2,4-dichloro-6-methyl-3-nitropyridine 6-methyl-3-nitropyridin-2,4-diol (1.7 g, 10 mmol) was dissolved in 10 mL POCl3, heated to 95C, and stirred for 1.5 h. The excess POCl3 was removed through centrifugation. 100 mL ice water was carefully added. The reaction solution was extracted with ethyl acetate (80 mL*3). The organic phase was combined, washed with saturated brine, dried with anhydrous Na2SO4 and spinned to dryness to afford 1.773 g yellow powder with a yield of 85.7 %.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,4966-90-9, its application will become more common.

Reference:
Patent; Xuanzhu Pharmaco., Ltd.; EP2524917; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem