Category: pyridine-derivatives

Synthetic Route of 1121-76-2, 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. 1121-76-2, name is 4-Chloropyridine 1-oxide, molecular formula is C5H4ClNO, 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.

4-Chloropyridine-N-oxide (3.0 g, 23 mmol), 4-trifluoromethylphenylboronic acid (6.57 g, 34.6 mmol), K2CO3 (4.8 g, 35 mmol) and PdCl2(dppf) (470 mg, 0.57 mmol) were stirred in DMSO (40 mL) under vacuum for 30 min. The flask was flushed with nitrogen, and the mixture was heated to 80 C. for 10 min. Upon cooling, the mixture was diluted with methylene chloride and washed with 5% lithium chloride solution (5×), dried, concentrated, and the residue was purified by flash column chromatography (40 g ISCO column eluting with methylene chloride and a methanol/ammonia mixture (10:1); gradient 100% methylene chloride to 80% methylene chloride over 30 min at 40 mL/min) to provide the title compound (1.90 g, 34%) as a tan solid: ESI MS m/z 240 [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 1121-76-2, 4-Chloropyridine 1-oxide.

Reference:
Patent; ALBANY MOLECULAR RESEARCH, INC.; US2011/3793; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 126053-15-4, Adding some certain compound to certain chemical reactions, such as: 126053-15-4, name is 4-Chloro-6,7-dihydro-5H-cyclopenta[b]pyridin-7-ol,molecular formula is C8H8ClNO, 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 126053-15-4.

A solution of intermediate 38 (0.92 mmol), 4-chloro-6,7-dihydro- 5/-/-cyclopenta[b]pyridin- 7-ol (1 mmol), hydrogen chloride in dioxane 4M (46mul) in CH3CN (10ml) was heated at 65C for 5 hours. K2CO3 10% aqueous solution and EtOAc were added. The reaction mixture was extracted, the organic layer was separated, dried over MgSO4, filtered and evaporated. The residue (0.4g) was purified by high-performance liquid chromatography (Stability Silica 5mum 150×30. Omm). Mobile phase (NH4OH 0.2%; gradient CH2CI2/CH3OH from 98/2 to 88/12), yielding 49mg compound 63 and 114mg of compound 64.

According to the analysis of related databases, 126053-15-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; WO2009/37308; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 7598-35-8, 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. 7598-35-8, name is 2-Bromopyridin-4-amine. A new synthetic method of this compound is introduced below.

To a solution of 2-bromopyridin-4-amine (75 g, 433 mmol) in pyridine (750 mL) stirred under nitrogenat 0C was added 2,5-dichloropyridine-3-sulfonyl chloride (128 g, 520 mmol) portionwise. The reactionmixture was stirred at room temperature for 16 h. After this time, pyridine was evaporated under reduced pressure to obtain a crude residue which was poured into ice water. The resulting solid was collected by filtration and dried. The solid was dissolved in EtOAc (2 L) and the organic layer was washed with 10% EDTA solution (2 L). The organic phase was dried over Na2SO4, filtered andconcentrated under reduced pressure to afford the title compound (120 g) as a brown solid. LCMS (Method G) Rt = 2.16 mi [M+H] = 381.9/383.9/385.9.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,7598-35-8, 2-Bromopyridin-4-amine, and friends who are interested can also refer to it.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; ANDERSON, Niall Andrew; BARTON, Nicholas Paul; CAMPOS, Sebastien Andre; CANNONS, Edward Paul; COOPER, Anthony William James; DOWN, Kenneth David; DOYLE, Kevin James; HAMBLIN, Julie Nicole; INGLIS, Graham George Adam; LE GALL, Armelle; PATEL, Vipulkumar Kantibhai; PEACE, Simon; SHARPE, Andrew; WHITE, Gemma Victoria; (157 pag.)WO2017/137535; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 113118-81-3, 5-Bromonicotinaldehyde, 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, 113118-81-3, blongs to pyridine-derivatives compound. Recommanded Product: 113118-81-3

To a solution of 5-bromonicotinaldehyde (XXV) (5.0 g, 26.9 mmol) in DCE (108 mL) was added dimethylamine-HCl (4.39 g, 53.8 mmol) and TEA (7.5 g, 53.8 mmol). The reaction was stirred at room temperature for 1 h. NaBH(OAc)3 was added and the reaction was stirred overnight at room temperature. The reaction was diluted with DCM and sat. aq. NaHCC . The organic layer was separated, washed with water, brine, dried and concentrated under vacuum to produce l-(5-bromopyridin-3-yl)-N,N-dimethylmethanamine (XXVI) as a brown liquid (92.6% yield). NMR (CDCI3) delta ppm 2.15 (s, 6H), 3.43 (s, 2H), 7.94 (s, 1H), 8.47 (d, J=2Hz, 1H), 8.59 (d, J=3Hz, 1H); ESIMS found for C8HnBrN2 mlz 215 (MBr79+H) and 217 (MBl81+H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,113118-81-3, its application will become more common.

Reference:
Patent; SAMUMED, LLC; DESHMUKH, Vishal; MURPHY, Eric Anthony; HOOD, John; (232 pag.)WO2018/75858; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 16830-24-3 ,Some common heterocyclic compound, 16830-24-3, molecular formula is C8H9NO2, 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.

A. Preparation of 4-Hydroxymethyl-2-methylpyridine STR240 To a suspension of 95% lithium aluminum hydride (2.4 g, 0.06 mol) in 150 mL of anhydrous ether was added a solution of methyl 2-methylisonicotinate1 (14.0 g, 0.093 mol) in 50 mL of anhydrous ether, at -5 C. under N2. The resulting mixture was stirred at room temperature for 30 min and was then refluxed for 2 h. An additional 1.2 g (0.03 mole) of lithium aluminum hydride was added portionwise and refluxing was continued for 1 h. The reaction mixture was then cooled at 0 C. and treated successively with 3.75 mL H2 O, 3.75 mL 15% aqueous NaOH and finally 11.25 mL of H2 O. This suspension was then filtered and the filter cake was washed with ether and then ethyl acetate. The filtrate was evaporated to give a dark yellow oil which was taken up in acetonitrile and then filtered through a pad of silica gel (elution with acetonitrile and then acetone). This gave the product (7.7 g, 67%) as a yellow oil: 1 Hnmr (CDCl3) delta8.30, 7.10 (ABq, J=5 Hz, 2H), 7.17 (s, 1H), 5.42 (s, –OH), 4.70 (s, CH2), 2.50 (s, CH3).

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. 16830-24-3, Methyl 2-methylisonicotinate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Bristol-Myers Company; US4644061; (1987); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 159503-91-0, 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 159503-91-0, name is tert-Butyl 4-bromo-5,6-dihydropyridine-1(2H)-carboxylate. This compound has unique chemical properties. The synthetic route is as follows.

2nd step: the metal lithium (1.0g, 0 . 15mol) and double (diisopropylamine) boron bromide (21.8g, 75mmol) by adding 2-methyl tetrahydrofuran (90 ml) in, temperature control -20 C to -10 C, dripping is dissolved in 2-methyl tetrahydrofuran (35 ml) of in N-Boc-1, 2, 5, 6-tetrahydro-pyridine-4-bromo (18.9g, 72mmol), stirring after 5 hours, the end of the detection reaction, adding npg (8.6g, 83mmol), heating to reflux reaction. Cooling, adding 10% hydrochloric acid aqueous solution to adjust PH= 5-6, organic layer by adding 10% palladium carbon (1.2g), after the replacement of nitrogen, filled with 1 atmospheric pressure hydrogen, after the reaction, drying of the organic layer, by adding 45 ml normal heptane cooling -10 C pulping, filtering to obtain 14.3g kind of white solid N-Boc-piperidin-4-boronic acid new pentamethylene glycol ester, GC: 98.5%, HNMR: > 98%, yield: 67%.

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 159503-91-0, tert-Butyl 4-bromo-5,6-dihydropyridine-1(2H)-carboxylate.

Reference:
Patent; Puri Cangzhou Orient Technology Co., Ltd.; Leng, Yanguo; Feng, Xuemin; Gui, Wenwu; (6 pag.)CN105566368; (2016); A;,
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. 106877-33-2, name is 5-Amino-2-(trifluoromethyl)pyridine, 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. Computed Properties of C6H5F3N2

Example 92:(R)-l-(4-(Trifluoromethyl)phenyl)-N-(6-(trinuoromethyl)pyridin-3-yl)-3,4- dihydroisoquinoline-2(lH)-carboxamide; To a solution of (R)-4-nitrophenyl l-(4-(trifluoromethyl)phenyl)-3,4-dihydroiso- quinoline-2(lH)-carboxylate (70 mg, 158 mumol, example 88) in MeCN (0.5 mL) was added 3-amino-6-(trifluoromethyl)pyridine (77 mg, 475 mumol). The resulting mixture was then subjected to a microwave irradiation at 150 C for 15 min and at 180 C for 15 min. Then, sodium hydride, 60% dispersion in mineral oil (18 mg, 475 mumol) was added and the mixture was stirred at RT for overnight. Then, H2O (0.5 mL) was added and the solvents were removed. The residue was then dissolved in a solution of MeOH and DMSO (1 :1. 1.0 mL). The solution mixture was purified by preparative HPLC (0%-100% MeCN 0.1% TFA/H2O 0.1% TFA) to give the desired product, which was then dissolved in MeOH (1.0 mL). The solution was then washed through PL-HCO3 MP resin (polymerlabs, 200 mg/6 mL tube) and the resin was washed with MeOH (2 x 0.5 mL). The combined washings were then concentrated and dried under vacuum to give the title compound as a yellow solid. MS (ESI, positive ion) m/z: 466 (M+H).

With the rapid development of chemical substances, we look forward to future research findings about 106877-33-2.

Reference:
Patent; AMGEN INC.; WO2009/73203; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 504-24-5, 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 504-24-5, name is 4-Aminopyridine. This compound has unique chemical properties. The synthetic route is as follows.

EXAMPLE 6 Compounds of the following general formula II-6 may be synthesised, for example, by the following methods. 3-Bromo-4-aminopyridine (1). 4-Aminopyridine (3.0 g, 31.9 mmol) was dissolved in 100 mL of DCM and 60 mL CH3CN. Bromine (5.1 g, 31.9 mmol) was added to this solution dropwise and the solution was stirred for 2 h. Sodium carbonate (6.2 g, 73.8 mmol) was added to the mixture and the reaction was stirred overnight. TLC (EtOAc) analysis of the reaction mixture showed two major spots, the higher running was 4-amino-3,5-dibromopyridine and the lower running one was the desired product (Rf=0.4, EtOAc). The reaction mixture was filtered and the filtrate was concentrated and chromatographed on a minimum amount of silica gel to yield 1.4 g (26%) of the desired product. 1H NMR (CDCl3): delta 8.39 (s, 1H), 8.10 (d, 1H), 6.60 (d, 1H), 4.74 (bs, 2H).

According to the analysis of related databases, 504-24-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Ferraris, Dana V.; Li, Jia-He; Kalish, Vincent J.; Zhang, Jie; US2003/22883; (2003); 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.183208-22-2, name is 5-Bromo-1-methyl-1H-pyrrolo[2,3-b]pyridine, molecular formula is C8H7BrN2, molecular weight is 211.06, as common compound, the synthetic route is as follows.SDS of cas: 183208-22-2

To a solution of tert-butyl (S)-2-(methoxymethyl)pyrrolidine-1-carboxylate (663 mg, 3.08mmol) in DCM (10 mL) was added trifluoroacetic acid (1.76 g, 15.40 mmol) within 5 min at0C. The mixture was warmed up to room temperature within 2 h and carefully poured into a10% NaOH solution (60 mL). After extraction with DCM (2 × 50 mL) the combined organicphases were dried over MgSO4, and evaporated. The residue was dissolved in DCM (5 mL)and N,N-diisopropylethylamine (521 mg, 4.03 mmol) was added at room temperature. Thissolution containing the deprotected pyrrolidine was then stirred until it was needed.A two-neck flask was charged with 5-bromo-1-methyl-1H-pyrrolo[2,3-b]pyridine (3)(500 mg, 2.37 mmol) and dry THF (30 mL) under argon. The solution was cooled to -80 C inan ethanol/nitrogen cooling bath and t-BuLi (1.4 M in pentane, 1.69 mL, 2.37 mmol) wasS 6added dropwise. The reaction mixture was warmed up to -75 C within 10 min and transferredto a solution of DABCO-bis(sulfur dioxide) (569 mg, 2.37 mmol) in dry THF (15 mL) at -75C. The cooling bath was removed after 30 min and the reaction mixture warmed up to roomtemperature. The THF solvent was removed under reduced pressure and dry DCM (20 mL)was added. N-Chlorosuccinimide (379 mg, 2.84 mmol) was slowly added as a solution in dryDCM (5 mL) followed by dropwise addition of the deprotected pyrrolidine. After the additionof water (35 mL) the mixture was extracted with DCM (2 × 20 mL). The combined organicphases were dried over MgSO4, and evaporated. Column chromatographic purification (SiO2,CH/EtOAc, 2:1) yielded a colorless, crystalline solid [291 mg, 40% yield].MP: 66 – 67 C (CH/EtOAc).1H-NMR (300 MHz, CDCl3): delta = 1.50-1.60 (m, 2H, 13-CHa, 14-CHa), 1.79-1.89 (m, 2H,13-CHb, 14-CHb), 3.08-3.18 (m, 1H, 15-CHa), 3.34-3.42 (m, 1H, 16-CHa), 3.38 (s, 3H,18-CH3), 3.44-3.52 (m, 1H, 15-CHb), 3.68 (dd, 2JH,H = 9.2 Hz, 3JH,H = 3.8 Hz, 1H, 16-CHb),3.71-3.81 (m, 1H, 12-CH), 3.95 (s, 3H, C-19), 6.60 (d, 3JH,H = 3.5 Hz, 1H, 3-CH), 7.33 (d,3JH,H = 3.5 Hz, 1H, 2-CH), 8.39 (d, 4JH,H = 2.1 Hz, 1H, 4-CH), 8.80 (d, 4JH,H = 2.1 Hz, 1H,6-CH) ppm.13C-NMR (75 MHz, CDCl3): delta = 24.1 (t, C-14), 28.9 (t, C-13), 31.7 (q, C-19), 49.5 (t, C-15),59.1 (q, C-18), 59.3 (d, C-12), 75.3 (t, C-16), 101.2 (d, C-3), 119.7 (s, C-9), 125.7 (s, C-5),129.0 (d, C-2), 131.7 (d, C-4), 142.0 (d, C-6), 149.0 (s, C-8) ppm.ESI(+)-MS: calcd. for C14H19N3O3S + H+, 310.1220; found 310.1220.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,183208-22-2, 5-Bromo-1-methyl-1H-pyrrolo[2,3-b]pyridine, and friends who are interested can also refer to it.

Reference:
Article; Waldmann, Christopher M.; Hermann, Sven; Faust, Andreas; Riemann, Burkhard; Schober, Otmar; Schaefers, Michael; Haufe, Guenter; Kopka, Klaus; Bioorganic and Medicinal Chemistry; vol. 23; 17; (2015); p. 5734 – 5739;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 10592-27-5, 2,3-Dihydro-1H-pyrrolo[2,3-b]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, Formula: C7H8N2, blongs to pyridine-derivatives compound. Formula: C7H8N2

Control the temperature below 20 degrees Celsius, dihydro-7-azaindole 120kg dissolved in 1200kg of hydrogen bromide dubbed the solution,Control the temperature of 20-30 degrees Celsius, slowly dropping hydrogen peroxide 120kg, add the continued reaction for 5 hours, and then to the reaction solution by adding sodium hydroxide to adjust, and then filtered, washed, centrifuged 0.5 hours, dried product 130kg dihydro-5-bromine -7-azaindole.

The synthetic route of 10592-27-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NANTONG ABA CHEMICALS CO., LTD.; WU, ZHENGGUANG; NIU, YUEHUI; LYU, JIAN; (5 pag.)CN106188050; (2016); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem