Category: pyridine-derivatives

Synthetic Route of 869108-35-0 , The common heterocyclic compound, 869108-35-0, name is Methyl 3-fluoropyridine-2-carboxylate, molecular formula is C7H6FNO2, 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.

Synthesis of Compound 66:; To a solution of LDA (1.8M in THF/heptane ; 72.0 ml_ ; 129 mmol ; 2.1 eq.) in THF (60 ml_) at -78C was added ierf-butylacetate (20.0 ml_ ; 148 mmol ; 2.4 eq.). The deep red solution was stirred at -78C for 45 minutes and maintained at that temperature during the slow addition of a solution of compound 63 (9.5 g ; 62 mmol ; 1 eq.) in THF (60 mL). The reaction mixture was then stirred for an additional 2 hours and quenched at -78C by addition of MTBE (150 mL) and water/acetic acid (1 :1 ; 150 mL). After warming up to room temperature, the layers were separated and the aqueous phase was extracted with MTBE (2 chi 100 mL). The combined organic phases were washed with water (300 mL) and brine (300 mL), dried over Na2S04, filtered and evaporated to dryness to afford compound 66 as an yellow oil (16.2 g ; contaminated with 8.5% W of acetic acid ; yield = 00%).

The synthetic route of 869108-35-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CRITICAL OUTCOME TECHNOLOGIES INC.; DANTER, Wayne; THRELFALL, Clinton; GUIZZETTI, Sylvain; MARIN, Julien; WO2011/120153; (2011); A1;,
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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. 1822-51-1, name is 4-(Chloromethyl)pyridine hydrochloride, the common compound, a new synthetic route is introduced below. Product Details of 1822-51-1

EXAMPLE 6; 4-[(R)-2-(4-benzyl-phenoxymethyl)-pyrrolidin-1-ylmethyl]-pyridine; To a solution of Example 1 (0.25 g, 0.82 mmol) in dichloromethane (2 mL) was added 4-picolyl chloride hydrochloride (0.13 g, 0.79 mmol) and triethylamine (0.29 mL, 2.08 mmol). The resulting mixture was stirred at ambient temperature overnight. The crude product was extracted into dichloromethane and washed with water followed by brine. The combined organic layers were dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The crude product was purified by flash chromatography using hexane/EtOAc (gradient system) to give the title compound (0.11 g, 45%); 1H NMR (400 MHz, CDCl3); delta 1.70-1.81 (m, 3H), 2.03 (m, 1H), 2.27 (m, 1H), 2.94-3.03 (m, 2H), 3.49 (d, J=14.4 Hz, 1H), 3.86 (m, 1H), 3.92 (s, 2H), 3.94 (m, 1H), 4.19 (d, J=14.4 Hz, 1H), 6.79 (d, J=8.8 Hz, 2H), 7.08 (d, J=8.8 Hz, 2H), 7.15-7.20 (m, 3H), 7.26-7.29 (m, 4H), 8.51 (m, 2H); MS (m/z) 359.5 (M+1); LC (99.7%); HPLC (91.6%)

The synthetic route of 1822-51-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DECODE CHEMISTRY, INC.; US2007/66820; (2007); A1;,
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Synthetic Route of 69627-02-7, 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. 69627-02-7, name is Thieno[3,2-b]pyridin-7(4H)-one, molecular formula is C7H5NOS, 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.

5.00 g of [3,2-b]pyridin-7-ol (33 mmol) and 50 g of phosphorus oxybromide (174 mmol) are put in a flask and heated at 1100C for 3h. The hot reaction mixture is poured into mixture of ice and 5N NaOH and extracted with CHC12, dried over Na2SO4 and evaporated. The crude product is applied onto a silica-gel chromatography column (Hexane :AcOEt=3:l) to give 4.19 g of the title compound . Yield 59%. mass spectrum (m/e):215(M+l); IH-NMR(CDCl3): 8.55(d, IH, J=4.3Hz), 7.86(d, IH, J=5.7Hz), 7.69(d, IH, J=5.7Hz), 7.49(d, IH, J=4.3Hz) ppm.

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 69627-02-7, Thieno[3,2-b]pyridin-7(4H)-one.

Reference:
Patent; ELI LILLY AND COMPANY; WO2006/107784; (2006); A1;,
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Pyridine | C5H5N – PubChem

Application of 944401-77-8, 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. 944401-77-8, name is 2-Amino-4-fluoropyridine, molecular formula is C5H5FN2, 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.

0294] Solid NBS (78 mg, 0.43 mmol) was added to a solution of 3-fluoropyridin-2-amine HCl salt (162 mg, 0.72 mmol) in ACN (4 mL) at RT with stirring. The reaction was shielded from light and stirred under nitrogen. After 1.5 h, an additional amount of NBS (15 mg, 0.084 mmol) was added to the reaction. Checking the reaction again after 1.5 h, an additional amount of NBS (15 mg, 0.084 mmol) was added to the reaction until the starting material had been consumed by LCMS. After 1 h7 the solvent was removed under reduced pressure and the residue purified by silica flash chromatography eluting with 50% ethyl acetate/hexane to afford 5-bromo-4-fluoropyridin-2-amine as a ivory solid (92 mg, 68%). LC/MS (m/z): 190.9/192.9 (MH+), Rt 1.02 minutes.

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 944401-77-8, 2-Amino-4-fluoropyridine.

Reference:
Patent; NOVARTIS AG; WO2007/84786; (2007); A1;,
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Pyridine | C5H5N – PubChem

Application of 641569-94-0, 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.641569-94-0, name is 4-Methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzoic acid, molecular formula is C17H14N4O2, molecular weight is 306.32, as common compound, the synthetic route is as follows.

Dissolve 4-Methyl-3-[[4- (3-pyridinyl) -2-pyrimidinyl] amino] benzoic acid (16.6 mg) and compound D (20 mg) in CH2Cl2 (0.5 mL),N, N-diisopropylamine (14 uL),N, N-Dimethyl-4-aminopyridine (3.3 mg),1- (3-Dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride (15.5 mg) was added and allowed to stir at room temperature. The mixture was stirred overnight, washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over sodium sulfate and filtered. The obtained filtrate was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (chloroform: methanol = 95: 5 ? 9: 1) to obtain IMT-5 precursor (tin compound) (34.6 mg, white solid).

Statistics shows that 641569-94-0 is playing an increasingly important role. we look forward to future research findings about 4-Methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzoic acid.

Reference:
Patent; Kyoto University; Arkray Corporation; Saji, Hideo; Kimura, Hiroyuki; Matsuda, Hirokazu; Soma, Tasukukei; Nakanishi, Shuichi; (26 pag.)JP2019/64987; (2019); A;,
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Related Products of 754131-60-7, 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 754131-60-7, name is 3-Bromo-2-(bromomethyl)pyridine. This compound has unique chemical properties. The synthetic route is as follows.

To a stirred solution of the above crude 3-bromo-2-bromomethylpyridine (70g, 0. 28MOL) in dioxane (SOOML) and water (250mL), was added NACN (28g, 0. 74MOL) at 0C and then stirred at RT for 16h. The reaction mixture was quenched with 3Lit of water and extracted with ethylacetate (4X500ML). The organic layer was washed with water (400L), brine (250mL), dried over NA2SO4 and concentrated to give crude product. The crude was purified by column chromatography over silica gel (pet. ether/ethylacetate, 8: 2) to give 3- BROMOPYRIDINE-2-YL-ACETONITRILE (22g, 40%). [TLC: Pet. ether/ethylacetate, 7: 3, RF= 0. 35] MS (EST) : 199.2 ; MS (ESR) : 197.2.

According to the analysis of related databases, 754131-60-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; APPLIED RESEARCH SYSTEMS ARS HOLDING N. V.; WO2004/98607; (2004); A1;,
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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. 694-85-9, name is 1-Methylpyridin-2(1H)-one, molecular formula is C6H7NO, 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. HPLC of Formula: C6H7NO

0.8mmol), compound A-3 (0.4mmol, 1 eq.), Three times with nitrogen was added 3mLpermuted dimethylsulfoxide (DMSO), injection of 100muL (0.80mmol) Compound B-1, wasstirred for 24 hours under blue light , compound C-3. The yield was 60percent.

With the rapid development of chemical substances, we look forward to future research findings about 694-85-9.

Reference:
Patent; Zunyi Medical College; He, Chunyang; Li, Xiaofei; (12 pag.)CN105669546; (2016); A;,
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Reference of 903522-29-2, 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.903522-29-2, name is 3,5-Difluoroisonicotinic acid, molecular formula is C6H3F2NO2, molecular weight is 159.09, as common compound, the synthetic route is as follows.

3,5-Difluoropyridine-4-carboxylic acid (0.510 g, 3.14 mmol) was added to anoven dried 250 mL round bottom flask. The flask was sealed with a septum, purged with nitrogen, and anhydrous THF (50mL) was added. Next, triethylamine (0.542 mL, 3.77 mmol) was added via syringe. The solution was sonicated until itbecame homogeneous, then ethyl chloroformate (0.372 mL, 3.77 mmol) was added. The reaction was stirred for 30 min.before being filtered through a short pad of Celite into a separate oven dried 250 mL round bottom flask. NaBH4 (0.261 g,6.91 mmol) was added followed by MeOH (5 mL). The reaction was stirred for 45 min. at room temperature. A samplealiquot was taken from the reaction, dissolved in HPLC grade MeCN (1 mL), and analyzed with LC-MS to confirm thecompletion of the reaction. The reaction was quenched with sat. ammonium chloride and diluted with EtOAc (150 mL).The organic layer was washed with DI water (50 mL) and brine, then dried over sodium sulfate and condensed to give a yellow oil. The oil was dissolved in DCM and purified by flash chromatography (5 g SiO2 cartridge, 0-12% MeOH/DCMgradient) to give the title compound as a clear semisolid (0.285 g, 63%). This compound has been previously reported andcharacterized (CAS 924649-16-1). 1H NMR (300 MHz, CDCl3) d = 4.81 (s, 2H), 8.28 (s, 2H) 8.30 (s, 2 H).

Statistics shows that 903522-29-2 is playing an increasingly important role. we look forward to future research findings about 3,5-Difluoroisonicotinic acid.

Reference:
Article; Porter, Jacob D.; Vivas, Oscar; Weaver, C. David; Alsafran, Abdulmohsen; DiMilo, Elliot; Arnold, Leggy A.; Dickson, Eamonn J.; Dockendorff, Chris; Bioorganic and Medicinal Chemistry Letters; vol. 29; 23; (2019);,
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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. 10386-27-3, name is 2-Bromoisonicotinonitrile. A new synthetic method of this compound is introduced below., Application In Synthesis of 2-Bromoisonicotinonitrile

To a solution of 2-(pyridin-2-yl)-4,5,6,7-tetrahydrooxazolo[4,5-c] pyridine (I- 23.4) (40 mg, 0.2 mmol) in DMF (2 mL) was added 2-bromoisonicotinonitrile (54 mg, 0.3 mmol), DIEA (52 mg, 0.4 mmol). The mixture was heated to 1000C and stirred for 16 h. The mixture was cooled to room temperature and poured into water. The mixture was extracted with EtOAc. The combined organic phase was dried over anhydrous Na2SO4 and concentrated. The residue was purified by preparative TLC to afford 2-(2- (pyridin-2-yl)-6,7-dihydrooxazolo[4,5-c]pyridin-5(4H)-yl)isonicotinonitrile (10 mg, 17percent) as a yellow solid. 1H NMR (400 MHz, CDCl3): delta 8.67 (d, IH), 8.25 (d, IH), 8.03 (d, IH), 7.75 (t, IH), 7.30 (t, IH), 6.81 (s, IH), 6.75 (d, IH), 4.52 (s, 2H), 4.07 (t, 2H), 2.91 (t, 2H); LC/MS: m/e = 304 (M+H)+.

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, 10386-27-3, 2-Bromoisonicotinonitrile.

Reference:
Patent; SEPRACOR INC.; BURDI, Douglas; SPEAR, Kerry, L.; HARDY, Larry, Wendell; WO2010/114971; (2010); 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. 757251-62-0, name is 4-Chloro-N-methoxy-N-methylpyridine-2-carboxamide. This compound has unique chemical properties. The synthetic route is as follows. Safety of 4-Chloro-N-methoxy-N-methylpyridine-2-carboxamide

Step 2: Preparation of 1-(4-chloropyridin-2-yl)ethanone. To a solution of 4-chloro-N-methoxy-N-methylpicolinamide (11.25 g, 56.08 mmol) in THF (50 mL) at 0°Cwas added MeMgBr(28.O4mL, 84.12 mmol). The mixture was then stirred at r.t. overnight and quenched withsaturated aqueous NH4C1. The resulting mixture was extracted with EtOAc. The organic layer was dried over anhydrous Na2SO4 and concentrated. The residue was purified by flash chromatography to give the desired product. ?H NMR (400 MHz, CDC13): 8.52(d, J = 5.2 Hz, 1H), 7.96 (s, 1H), 7.40 (d, J = 5.2 Hz, 1H), 2.64 (s, 3H).LC-MS: mz 156.0 (M+H).

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, 757251-62-0, 4-Chloro-N-methoxy-N-methylpyridine-2-carboxamide.

Reference:
Patent; AGIOS PHARMACEUTICALS, INC.; KONTEATIS, Zenon D.; POPOVICI-MULLER, Janeta; TRAVINS, Jeremy M.; ZAHLER, Robert; CAI, Zhenwei; ZHOU, Ding; WO2015/3640; (2015); A1;,
Pyridine – Wikipedia,
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