Category: pyridine-derivatives

Application of 33252-28-7, 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. 33252-28-7, name is 6-Chloronicotinonitrile, molecular formula is C6H3ClN2, 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.

Step 1: 6-Isopropoxynicotinonitrile (48). To a stirring suspension of Potassium tert-butoxide (6.0 g, 54.12 mmol) in THF (200 mL) at 0 C. was added isopropanol (4.17 mL, 54.13 mmol) and the reaction mixture was stirred for 5 min. Compound 47 (5.0 g, 36.08 mmol) was added at 0 C. and the reaction mixture was stirred for 2 h at room temperature. The reaction mixture was concentrated in vacuo, the resulting residue was dissolved/suspended in water and extracted with EtOAc. The combined organic layers were washed with sat. NaCl, dried and concentrated to afford 48 (5.6 g) which was used as such for the next step.

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 33252-28-7, 6-Chloronicotinonitrile.

Reference:
Patent; Exelixis, Inc.; US2010/249071; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 947249-13-0, Adding some certain compound to certain chemical reactions, such as: 947249-13-0, name is 5-Bromo-3-(difluoromethoxy)pyridin-2-amine,molecular formula is C6H5BrF2N2O, 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 947249-13-0.

A glass reaction vessel (bomb) was charged with a mixture of 5-bromo-3- (difluoromethoxy)pyridin-2-amme(8, 6.212 g, 26,0 mmol), Bis(pinacolato)diboron (6.93 g, 27.3 mmol), Pd2(dba)3(0.952 g, 1.040 mraol), tricyclohexylphosph»ne(l .020 g, 3.64 mmol), and KOAc(5.36 g, 56.4 mmol) in anhydrous dioxane(70 ml). The mixture was carefully sparged with argon, the reaction vessel sealed, and heated to about 1 1OC in an oil bath for 24 hours. LCMS of aliquot indicated complete conversion of 8 to product I4H ([M+H]« 205.0 as acid, /R – 0.27min), Reaction mixture was diluted with EtOAc(70ml) aftere it cooled down to ambient temperature, filtered through neutral alumina(~30ml, 2.5ml thickness), alumina cake was washed throughly with IUtOAc(IOOmI), and filtrate was combined, concentrated and a light brown solid residue was obtained. The brown residue was triturated in heptane( 100ml) at (PC, desired product precipitated out, was collected via filtration and filter cake was rinsed throughly with heptane, final product 14H was obtained as a yellow solid(7.777g, 74% yield, }M+H]:…205.0, /kappa = 0.27min) after dried under high vacuum. ‘ H NMR confirmed structure, and an unidentified impurity at ~1.3ppm was found by 1H NMR. This impurity peak was probable a pinacole t-Bu group, and -1 : 1 tnol ratio to product. 1H NMR (400 MHz, CDCl,) delta ppm 8,27 (d, ./ « 1.5 Hz, 1 H), 7.55 (a, 1 H), 6.51 (t, JF-H= 73.6 Hz, 1H), 1.27 (8, 12 VI).

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. 947249-13-0, 5-Bromo-3-(difluoromethoxy)pyridin-2-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NOVARTIS AG; HUANG, Zilin; SENDZIK, Martin; WO2010/100127; (2010); 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.29681-42-3, name is Methyl 4-bromopicolinate, molecular formula is C7H6BrNO2, molecular weight is 216.032, as common compound, the synthetic route is as follows.Application In Synthesis of Methyl 4-bromopicolinate

Step 1: 2-hydroxymethyl-4-bromopyridine Methyl 4-bromo-pyridine formate (990mg, 4.58mmol) and ethanol (250mL) were added to a 250mL reaction flask. Under stirring, sodium borohydride (380mg, 10mg) was slowly added to the reaction system in batches. The reaction mixture was stirred for 18 hours under the protection of nitrogen at room temperature. After completion of the reaction, 5mL acetone was added to the reaction system, followed by stirring for 15 minutes. The reaction solution was filtered, concentrated and added with ethyl acetate and water, and the layers were separated. The organic phase was dried and concentrated to obtain the title compound (yellow liquid, 760mg, 88%), the crude product was used directly for the subsequent reaction. (MS: [M+1] 187.9)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,29681-42-3, Methyl 4-bromopicolinate, and friends who are interested can also refer to it.

Reference:
Patent; Beijing Pearl Biotechnology Limited Liability Company; DONG, Jiaqiang; ZHONG, Boyu; YUAN, Hongbin; SHI, Quan; CHU, Shaosong; ZHANG, Deyi; ZHANG, Ruihao; (219 pag.)EP3150592; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 135900-33-3, 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.135900-33-3, name is 6-(Trifluoromethoxy)pyridin-3-amine, molecular formula is C6H5F3N2O, molecular weight is 178.11, as common compound, the synthetic route is as follows.

A mixture of Example 235C (0.095 g, 0.350 mmol), PyBOP ((1H- benzo[(i] [l ,2,3]triazol-l-yl)oxy)tri(pyrrolidin-l-yl)phosphonium hexafluorophosphate(V)) (0.219 g, 0.420 mmol), 6-(trifluoromethoxy)pyridin-3-amine (0.075 g, 0.420 mmol), and triethylamine (0.073 mL, 0.525 mmol) in N,N-dimethylformamide (DMF) (3 mL) was stirred for 3 hours. The reaction mixture was quenched with brine and saturated NaHC(, and extracted with ethyl acetate (2x). The combined organic layers were washed with brine, dried over (1679) MgSO/t, filtered, and concentrated. The residue was purified on a 12 g column using the Biotage Isolera One flash system eluted with heptanes/ethyl acetate (7:3 to 6:4) to provide the title compound (65.1 mg, 43%). MS (ESI+) nt/z 432.3 (M+H)+.

Statistics shows that 135900-33-3 is playing an increasingly important role. we look forward to future research findings about 6-(Trifluoromethoxy)pyridin-3-amine.

Reference:
Patent; CALICO LIFE SCIENCES LLC; ABBVIE INC.; MARTIN, Kathleen, Ann; SIDRAUSKI, Carmela; PLIUSHCHEV, Marina, A.; FROST, Jennifer, M.; TONG, Yunsong; XU, Xiangdong; SHI, Lei; ZHANG, Qingwei, I.; XIONG, Zhaoming; SWEIS, Ramzi, Farah; DART, Michael, J.; MURAUSKI, Kathleen; (288 pag.)WO2019/90074; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 6268-43-5, 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.6268-43-5, name is 1,3-Di(pyridin-2-yl)urea, molecular formula is C11H10N4O, molecular weight is 214.22, as common compound, the synthetic route is as follows.

For R3 = NH-py and R1 = py in Example Scheme ES, the following example can be listed:? Using 10.0 mol% Zn(OAc)2.17H20, 1.0 equiv ACDG-NH-CO-NH-ACDG 5a, 52.0 equivisopropanol (ha), 140 C 24 h, a GO-yield of 59% of 2-aminopyridine (6a) was determinedwith TMB as an internal standard (calculated based on the formation of 2.0 equiv 2- aminopyridine (6a) = 100 % GO-yield).

The chemical industry reduces the impact on the environment during synthesis 6268-43-5, I believe this compound will play a more active role in future production and life.

Reference:
Patent; UNIVERSITEIT ANTWERPEN; MAES, Bert; WYBON, Clarence; CHEN, Chen; BHEETER, Charles Beromeo; SERGUEEV, Serguei; (88 pag.)WO2017/46133; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 693286-31-6, Adding some certain compound to certain chemical reactions, such as: 693286-31-6, name is 4,6-Dichloro-2-methylnicotinic acid,molecular formula is C7H5Cl2NO2, 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 693286-31-6.

To a solution of 4, 6-dichloro-2-methyl-nicotinic acid (8. 5 g, 41.3 mmol) in anhydrous tetrahydrofuran (85 mL), 1,3-dicyclohexyl-carbodiimide (9.27 g, 44.9 mmol), 4- (DIMETHYLAMINO)-PYRIDINE (140 mg, 1.14 mmol), and cyclopentanol (5.1 mL, 4. 83 g, 56.2 mmol) are added in succession. The mixture is stirred for 15 minutes at room temperature and brought to reflux at which it is maintained for 1 hour. The reaction is cooled to ambient temperature and all volatiles are removed in vacuo. The residue is dissolved in a mixture of ethyl acetate and hexane (1: 12,200 mL) and the resultant suspension is filtered over a small pad of silica gel (45 g), which is subsequently rinsed with additional 200 mL of the same mixture of hexane and ethyl acetate. The obtained solution is concentrated in vacuo and the residue chromatographed on silica gel (hexane: ethyl acetate 15: 1) to afford 4, 6-dichloro-2- methyl-nicotinic acid cyclopentane ester as colorless oil.

According to the analysis of related databases, 693286-31-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NEUROGEN CORPORATION; WO2004/43925; (2004); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1256789-09-9, Adding some certain compound to certain chemical reactions, such as: 1256789-09-9, name is Methyl 6-chloro-2,4-dimethylnicotinate,molecular formula is C9H10ClNO2, 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 1256789-09-9.

a) Synthesis of 2-(methoxymethyl)-4-methyl-6-morpholin-4-yl-pyridine-3-carboxylic acid methylesterTo a solution of 710 mg, (3.6 mmol) 6-chloro-2,4-dimethyl-pyridine-3-carboxylic acid methylester in CCI4 (16 ml) were added 688 mg (3.90 mmol) N-bromosuccinimide, 59 mg (0.36 mmol) AIBN and 210 muIota (3.72 mmol) acetic acid . The reaction mixture was irradiated with a 200W Wolfram lamp at 60 C for 24 h. The mixture was then filtered through celite, washed with CCI4 and concentrated in vacuo. After CC (hexane/EtOAc 97:3) of the residue a mixture of 6-chloro-2,4-dimethyl-pyridine-3-carboxylic acid methylester, 4-(bromomethyl)-6- chloro-2-methyl-pyridine-3-carboxylic acid methylester and 2-(bromomethyl)-6-chloro-4- methyl-pyridine-3-carboxylic acid methylester was obtained. This mixture was dissolved in dioxane (10 ml) and added at 0 C to a solution prepared by dissolving 594 mg (25.8 mmol) sodium in MeOH (11 ml) at 0 C. This reaction mixture was stirred at RT for 3 h. Then the reaction solution was poured into water and extracted with EtOAc. The organic layer was washed with water and brine, dried over Na2S04 and concentrated in vacuo. After CC (hexane/EtOAc 97:3) of the residue again a mixture of 6-chloro-4-(methoxymethyl)-2-methyl- pyridine-3-carboxylic acid methylester and 6-chloro-2-(methoxymethyl)-4-methyl-pyridine-3- carboxylic acid methylester was obtained. This material was dissolved in NMP (7.8 ml) and 860 muIota (9.85 mmol) morpholine and 1.36 g (9.85 mmol) K2C03 were added followed by heating at 100 C for 5 h. Then the mixture was poured into water and extracted with EtOAc. The organic layer was washed with water and brine, dried over Na2S04 and concentrated in vacuo. Purification of the residue by CC (hexane/EtOAc 9:1) provided 90 mg (0.32 mmol, 9%) 2-(methoxymethyl)-4-methyl-6-morpholin-4-yl-pyridine-3-carboxylic acid methylester.

According to the analysis of related databases, 1256789-09-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GRUeNENTHAL GMBH; KUeHNERT, Sven; BAHRENBERG, Gregor; KLESS, Achim; SCHROeDER, Wolfgang; LUCAS, Simon; WO2012/52167; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 33252-28-7, Adding some certain compound to certain chemical reactions, such as: 33252-28-7, name is 6-Chloronicotinonitrile,molecular formula is C6H3ClN2, 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 33252-28-7.

Example 29Step A6-Bromonicotinonitrile. 6-Chloronicotinonitrile (13.8 g, 100 mmol) was heated at 145 C in phosphorus tribromide (150 ml.) for 32 h. After cooling, the mixture was concentrated in vacuo. To the residue was added phosphorus tribromide (150 ml_), and the mixture was heated at 145 C for another 32 h. After cooling, the mixture was concentrated in vacuo, and an ice-water mixture (500 ml.) was added. Sodium bicarbonate was added to neutralize the mixture, and the product was extracted with ethyl acetate (3 chi 250 ml_). The combined organic extracts were washed with brine and dried over magnesium sulfate. The solvent was removed in vacuo, and the residue was chromatographed (hexanes-ethyl acetate) to give 14.9 g (81 %) of 6-bromonicotinonitrile as a white solid: 1 H NMR (400 MHz, CDCI3) S 7.66 (d, J = 1 1.0 Hz, 1 H), 7.80 (dd, J = 3.1 , 1 1.0 Hz, 1 H), 8.67 (d, J = 3.1 Hz, 1 H); MS (M+H)+ m/z=183.0, 185.0.

According to the analysis of related databases, 33252-28-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PFIZER LIMITED; BURGESS, Gary; WO2012/114223; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 79491-46-6, 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. 79491-46-6, name is 2,6-Dibromo-3-methoxy-5-nitropyridine, molecular formula is C6H4Br2N2O3, 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.

5.43 3-Methoxy-5-nitropyridine-2,6-diamine (33) A solution of 32 (0.5 g, 1.6 mmol) in aqueous ammonia (15 M, 12 mL, 180 mmol) was heated at 90 C for 1 h in a microwave oven. The reaction mixture was cooled, the yellow solid was collected by filtration, washed with a small amount of water, and dried under vacuum to afford 33 (230 mg, 78%) as a yellow solid: 1H NMR (400 MHz, DMSO-d6, 393 K) delta = 7.48 (s, 1H), 7.35 (br, 2H), 6.81 (br, 2H), 3.80 (s, 3H); MS ES+ve m/z 185 (M+H)+.

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 79491-46-6, 2,6-Dibromo-3-methoxy-5-nitropyridine.

Reference:
Article; Miah, Afjal H.; Abas, Hossay; Begg, Malcolm; Marsh, Benjamin J.; O’Flynn, Daniel E.; Ford, Alison J.; Percy, Jonathan M.; Procopiou, Panayiotis A.; Richards, Steve A.; Rumley, Sally-Anne; Bioorganic and Medicinal Chemistry; vol. 22; 15; (2014); p. 4298 – 4311;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 135900-33-3, 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. 135900-33-3, name is 6-(Trifluoromethoxy)pyridin-3-amine, molecular formula is C6H5F3N2O, 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.

A solution of Br2 (0.25 mL, 4.87 mmol) in HO Ac (3 mL) was added dropwise to a stirring solution of 6-(trifluoromethoxy)pyridin-3-amine (400 mg, 2.25 mmol) in EtOH (15 mL) and HO Ac (1.5 mL) at 0C under a nitrogen atmosphere. After addition was complete, the reaction was warmed to room temperature and was allowed to stir for an additional 15 hours. The reaction mixture was concentrated. DCM (30 mL) and saturated aqueous NaHC03 (20 mL) were added to the crude residue. The aqueous layer was extracted with DCM (50 mL x 3). The combined organic layers were dried over Na2S04, filtered and concentrated. The crude residue was purified by column chromatography (0-10% EtOAc in petroleum ether) to give 2,4- dibromo-6-(trifluoromethoxy)pyridin-3-amine (670 mg, yield: 89%) as light yellow solid. 1H NMR (400 MHz, CDCl3): d = 7.18 (s, 1H), 4.59 (s, 2H).

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 135900-33-3, 6-(Trifluoromethoxy)pyridin-3-amine.

Reference:
Patent; GENENTECH, INC.; STAFFORD, Jeffrey, A.; VEAL, James, M.; TRZOSS, Lynnie, Lin; MCBRIDE, Christopher; PASTOR, Richard, M.; STABEN, Steven, Thomas; STIVALA, Craig; VOLGRAF, Matthew; (200 pag.)WO2020/18970; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem