Pyridine-derivatives

Synthetic Route of 156072-84-3, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 156072-84-3 as follows.

[0307] Cesium carbonate (0.734 g, 2.25 mmol) and 5-chloro-3-methylpyridine-2-carbonitrile (0.206 g, 1.35 mmol) wereadded at room temperature to a suspension of the optically active form of cis-1-(diphenylmethyl)-5-hydroxy-3-(piperidin-4-yl)-4-(trifluoromethyl)-1,4,5,7-tetrahydro-6H-pyrazolo[3,4-b]pyridin-6-one (0.212 g, 0.451 mmol) produced in ReferenceExample 27 in DMSO (2 mL), and the mixture was stirred at 150C for 2 hours. The reaction suspension wascooled to room temperature, then diluted with ethyl acetate, and washed with brine. The obtained organic layer wasdried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residuewas purified by silica gel column chromatography [elute: hexane/ethyl acetate = 92/8 – 50/50 (gradient)] to obtain thetitle compound (0.226 g, yield: 86%, optically active form).[0308] 1H-NMR (400MHz, CDCl3) delta: 8.14 (1H, d, J=3Hz), 7.40-7.36 (6H, m), 7.12-7.06 (5H, m), 6.91 (1H, d, J=3Hz),6.69 (1H, s), 4.53 (1H, d, J=7Hz), 3.94-3.86 (3H, m), 3.69 (1H, d, J=3Hz), 3.08-3.00 (2H, m), 2.89-2.81 (1H, m), 2.45(3H, s), 2.02-1.80 (4H, m).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,156072-84-3, its application will become more common.

Reference:
Patent; Daiichi Sankyo Company, Limited; KOBAYASHI, Hideki; ARAI, Masami; KANEKO, Toshio; TERASAKA, Naoki; (95 pag.)EP3081566; (2016); A1;,
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 72093-03-9, name is 3-Chloro-2-methylpyridine. This compound has unique chemical properties. The synthetic route is as follows. Product Details of 72093-03-9

Preparation of teit-butyl 4-((3-chloropyridin-2-yl)methyl)-4- hydroxypiperidine-l-carboxylate. A solution of 3-chloro-2-methylpyridine (64.2 mg, 0.50 mmol) in THF (1 mL) was sparged with N2 and cooled to -78 C before n-butyllithium (2.5 M THF, 0.16 mL, 0.41 mmol) was added dropwise. After stirred at -78 C for 45 min, the mixture was warmed to RT and stirred for 2 h before cooled again to -78 C. A solution of tert-butyl 4-oxopiperidine-l-carboxylate (74.2 mg, 0.37 mmol) in THF (1.5 mL) was added dropwise. After stirring for 2 hr at -78 C, the mixture was warmed to rt and stirred for 2 d. The reaction was then partitioned between EtOAc and sat. H4CI (aq). After phase-separation, the aqueous was extracted with EtOAc (3x). The organic extracts were combined, dried over Na2S04, filtered and concentrated. The residue was purified by silica chromatography (10-90% EtOAc in hexanes) to afford the title compound as a colorless oil (103.5 mg, 85%). MS (apci) m/z = 227.1 (M+H-Boc).

With the rapid development of chemical substances, we look forward to future research findings about 72093-03-9.

Reference:
Patent; ANDREWS, Steven W.; ARONOW, Sean; BLAKE, James F.; BRANDHUBER, Barbara J.; COLLIER, James; COOK, Adam; HAAS, Julia; JIANG, Yutong; KOLAKOWSKI, Gabrielle R.; MCFADDIN, Elizabeth A.; MCKENNEY, Megan L.; MCNULTY, Oren T.; METCALF, Andrew T.; MORENO, David A.; RAMANN, Ginelle A.; TANG, Tony P.; REN, Li; WALLS, Shane M.; (946 pag.)WO2018/71454; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 912369-42-7, Adding some certain compound to certain chemical reactions, such as: 912369-42-7, name is Methyl 3-((tert-butoxycarbonyl)amino)picolinate,molecular formula is C12H16N2O4, 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 912369-42-7.

ter f-butyl f2-(hvdroxymethyl)py ridin-3-yll carbamate; To methyl 3-[(tert- butoxycarbonyl)amino]pyridine-2-carboxylate and methyl 2-[(tert- butoxycarbonyl)amino]nicotinate (5.00 g, 19.8 mmol) is added THF/MeOH (30 mL/3 mL) and the reaction is cooled to 0 C whereupon sodiumborohydride (1.49 g, 39.6 mmol) is added. The reaction is warmed to rt and stirred for four hours. The reaction mixture is then EPO dissolved in EtOAc and washed with saturated sodium bicarbonate solution. The organic layers are combined, dried over magnesium sulfate, filtered, and concentrated under reduced pressure to afford the title compound and tert-buty [3-(hydroxymethyl)pyridin-2- yljcarbamate which are separated by preparatory HPLC (5-95% MeCN/water/0.1% TFA). The desired isomer is confirmed by ID NOE NMR experiments. 1H NMR delta 8.78 (br s, IH), 8.17 (m, IH), 8.10 (d, IH), 7.27 (dd, IH), 4.64 (s, 2H), 1.46 (s, 9H). LCMS (ES, M+H=225).

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. 912369-42-7, Methyl 3-((tert-butoxycarbonyl)amino)picolinate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2006/106326; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1186194-46-6, 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 1186194-46-6, name is 5-Bromo-6-methoxynicotinic acid. This compound has unique chemical properties. The synthetic route is as follows.

Step 2: 1 -{[5-Bromo-6-methoxy-pyridine-3-carbonyl]-amino}-cycloheptanecarboxylic acid methyl esterThe compound of step 1 (1 .85 g, 7.97 mmol) was dissolved in thionyl chloride (6 ml) and stirred for 30 min at 60 C. The volatiles were evaporated in vacuo, the residue was dissolved in DCM and added to a stirred mixture of 1 -amino- cycloheptanecarboxylic acid methyl ester hydrochloride, EA and saturated sodium hydrogencarbonate solution with ice cooling. The mixture was stirred at room temperature overnight, the phases were separated and the aqueous phase was extracted with EA. The combined organic phases were dried over sodium sulfate and evaporated to dryness to yield the title compound (2.80 g).1H-NMR: delta = 8.62 (d, 1 H); 8.52 (s, 1 H); 8.48 (d, 1 H); 3.99 (s, 3H); 3.57 (s, 3H); 2.15- 2.01 (m, 4H); 1 .65-1 .43 (m, 8H)

According to the analysis of related databases, 1186194-46-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SANOFI-AVENTIS; PERNERSTORFER, Josef; KLEEMANN, Heinz-Werner; SCHAEFER, Matthias; SAFAROVA, Alena; PATEK, Marcel; WO2011/53948; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 84539-34-4, 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.84539-34-4, name is 4-Amino-3,5-dibromopyridine, molecular formula is C5H4Br2N2, molecular weight is 251.91, as common compound, the synthetic route is as follows.

(2) diazotization reaction:A 200 ml three-necked flask was charged with 0.045 mol of concentrated sulfuric acid having a concentration of 17.5 mol / L and 2.52 g (0.01 mol)3,5-dibromo-4-aminopyridine,After 3,5-dibromo-4-aminopyridine is completely dissolved,1.78g (0.014mol) nitrosylsulfuric acid was added dropwise at 52 C, the end of the reaction was tested by using potassium iodide starch test paper. When the reaction solution turned the potassium iodide starch test paper blue and did not fade, the reaction was stopped for 1.2h,To give 3,5-dibromo-4-pyridin-sulfonic acid

Statistics shows that 84539-34-4 is playing an increasingly important role. we look forward to future research findings about 4-Amino-3,5-dibromopyridine.

Reference:
Patent; Shanghai Wohua Chemical Co., Ltd.; Hu Yadong; Yang Benmei; (5 pag.)CN106957259; (2017); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 18699-87-1, 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 18699-87-1, name is 2-Methyl-3-nitropyridine. This compound has unique chemical properties. The synthetic route is as follows.

Add tetrahydrofuran (2.7 L) to a 22-L, 3-neck flask fitted with a stirrer, temperature probe and an addition funnel fitted with a gas inlet adapter for N2, and cool to about 2 C. Add sodium ethoxide (0.409 kg, 6.02 mol, 2.0 equiv.) in one portion. One observes a slight exotherm to 2.7 C. Stir the mixture for 20 min, add diethyl oxalate (1.22 L, 9.03 mol, 3.0 equiv.) at -0.34 C. over 50 min (slightly exothermic) and then stir the mixture for 10 min. Add a solution of 2-methyl-3-nitropyridine (2a-1, 0.415 kg, 3.01 mol, 1.0 equiv.) and THF (0.625 L) at 4-9 C. over 22 min without cooling. Allow the mixture to warm to rt over 1 h. Monitor progress of the reaction by HPLC (Agilent series 1100 using the following conditions: Waters Symmetry C8 (5mu) column (3.9×150 mm), flow rate at 1.0 mL/min; CH3CN/0.1% aq. TFA, 55/45; lambda=210 nm; RT: 2-methyl-3-nitropyridine 2a-1=1.8 min, 3a-1=2.7 min). Typically one observes >99% conversion to product within 2-3 h. During the reaction, a thick red precipitate forms. Cool the reaction mixture to about 1 C. and add saturated NH4Cl solution (2.0 L) at 1 C. to 9 C. Add water (5.9 L) (pH 7.4) and then add IPA (3.5 L). Stir the mixture for 1 h and collect the red colored solid by filtration. Wash the filter cake with IPA/H2O (1:4, 8.0 L), H2O (15 L) and air dry. Dry the filter cake (40 C./0.1 in Hg) to give 3a-1 (0.635 kg, 89%). 1H NMR (CDCl3) delta 1.40 (t, 3H, J=7 Hz), 4.38 (q, 2H, J=7 Hz), 7.36 (m, 2H), 8.42 (dd, 1H J=1.5, 8.4 Hz), 8.66 (dd, 1H, J=1.5, 4.8 Hz), 14.52 (2, 1H, OH).

According to the analysis of related databases, 18699-87-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Aventis Pharmaceuticals Inc.; US2005/131012; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 83393-46-8, 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. 83393-46-8, name is 1-(1H-Pyrrolo[2,3-b]pyridin-3-yl)ethanone, molecular formula is C9H8N2O, 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.

(E)-3-chloro-3-(lH-pyrrolo[2,3-b]pyridin-3-yl)acrylaldehyde:; Phosphorous oxychloride (3.7 mL, 40 mmol) was added dropwise to DMF (6.2 mL, 80 mmol) at 0 C. The reaction mixture was let warm to room temperature and stirred for 15 minutes. 1-(lH-Pyffolo[2,3-b]pyridin-3-yl)-ethanone was added in DMF (20 mL) and the reaction heated to 60 C for 4 hours, cooled to 0 C and 150 mL of saturated NaOAc solution added. The reaction mixture was heated briefly to 50 C and then extracted with EtOAc. The organic layer was washed with brine, dried over sodium sulfate and concentrated to an oil which contains impure product. Upon standing a solid precipitated from the aqueous layer to give 0.9 g of a brown solid, 4.3 mmol, 22% yield.

According to the analysis of related databases, 83393-46-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; WO2005/103050; (2005); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 112110-07-3, 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. 112110-07-3, name is 5-(Trifluoromethyl)pyridin-3-amine, molecular formula is C6H5F3N2, 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.

Under a nitrogen atmosphere, 0.1 g (0.25 mmol, 1.0 eq) of JD1001-002-12 was sequentially added to a 25 mL reactor.3.2 mL (10.0 V) THF, 0.32 g (0.75 mmol, 3.1 eq) NaHCO3, 0.38 g (0.75 mmol, 3.0 eq) 2-amino-5-trifluoromethylpyridine, heated to 60 C, stirred for 3 hours, TLC The reaction of the raw materials is detected (developing agent: PE/EA=1/1,UV254), the reaction was stopped, the reaction was quenched with water and extracted with ethyl acetate. Filtration and concentration of the organic phase gave a solid, which was purified by HPLC (CH3CN/H2O = 60:40) to afford 39 mg of JD1001-2111. Yield31%.

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 112110-07-3, 5-(Trifluoromethyl)pyridin-3-amine.

Reference:
Patent; Kunming Jida Pharmaceutical Co., Ltd.; Xiao Xuzhi; Zhang Poyong; Lu Faguan; Wang Zhipeng; Chen Mengran; Guo Kun; Zhou Rui; Zhang Yun; (28 pag.)CN109593061; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 727356-19-6, 2-Bromo-6-(chloromethyl)pyridine, 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: 2-Bromo-6-(chloromethyl)pyridine, blongs to pyridine-derivatives compound. name: 2-Bromo-6-(chloromethyl)pyridine

A214.1a (133 mmol) was dissolved in DMF (250 niL) and potassium phthalimide (54.2 g, 293 mmol) was added portionwise to maintain the internal temperature below 3O0C. An additional portion of DMF (50 mL) was used to rinse the flask and powder funnel used for the potassium phthalimide addition. The reaction was stirred at room temperature overnight after which the reaction was judged complete by HPLC analysis. Water (600 mL) was added slowly to the reaction and after 30 minutes of stirring the resulting precipitate was collected by filtration, washed with several portions of water (1000 mL total) and allowed to air dry. The resulting solid, which contained the desired product along with excess phthalimide, was resuspended in water (700 mL) and the solution was made basic by addition of 1 N NaOH (3 mL). After slurrying for 20 minutes the solids were collected by filtration, washed with several portions of water and allowed to air dry. The solid still contained some phthalimide so was resuspended in MeOH (50 mL) and water (800 mL) and allowed to stir vigorously for 2 days. The solid was again collected by filtration, then slurried in hot MeOH (200-300 mL), cooled to room temperature and filtered. The solid was air dried to afford the phthalimide adduct, A214.1, along with residual phthalimide as a white solid. This material was used without further purification for the next step.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,727356-19-6, 2-Bromo-6-(chloromethyl)pyridine, and friends who are interested can also refer to it.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2006/122137; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 67310-56-9 , The common heterocyclic compound, 67310-56-9, name is 1-(5-Hydroxypyridin-2-yl)ethanone, 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.

K2CO3 (504 mg, 3.65 mmol) followed benzylbromide (0.22 mL, 1.82 mmol) was added to a solution of 1-(5-hydroxypyridin-2-yl)ethanone (250 mg, 1.82 mmol) in MeCN (8 mL) at rt. The mixture was stirred at rt overnight and filtered. The filtrate was concentrated and the residue purified by chromatography to give the sub-title compound (360 mg, 1.58 mmol, 87 %).

The synthetic route of 67310-56-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ATROGI AB; PELCMAN, Benjamin; BENGTSSON, Tore; (93 pag.)WO2019/53427; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem