Category: pyridine-derivatives

Synthetic Route of 109613-97-0, 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. 109613-97-0, name is 2-Bromo-4-methoxypyridin-3-amine. A new synthetic method of this compound is introduced below.

To an ice-cold solution of 2-bromo-4-methoxypyridin-3-amine (Intermediate 38), (2.74 g) in pyridine (102 mL) was added ethyl chloroformate (1.91 mL) dropwise and then stirred at rt for 45 min. The reaction mixture was cooled in an ice-bath and more ethyl chloroformate (9 mL) added and the mixture left to stir overnight at rt. The reaction mixture was diluted with EtOAc and washed with sat. aq. NaHCO3. The aqueous layer was extracted with EtOAc and the combined organic layers washed with brine, dried over MgSO4, filtered and evaporated under vacuum to give a solid. Product was observed in the aqueous layer by LC-MS, so this was re-extracted with EtOAc (3*) and evaporated under vacuum to give a solid which was combined with the previous solid, dissolved in DCM and purified by column chromatography (normal phase, 50 g, Biotage SNAP cartridge KP-Sil, 50 mL/min, gradient 10-70% EtOAc in n-hexane) to give the desired product (2.35 g). LCMS: m/z 275.43 [M+H]+. 1H NMR (400 MHz, CDCl3) ppm 1.32 (t, J=7.1 Hz, 3H) 3.93 (s, 3H) 4.24 (q, J=7.1 Hz, 2H) 6.06 (br. s., 1H) 6.86 (d, J=5.6 Hz, 1H) 8.19 (d, J=5.6 Hz, 1H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,109613-97-0, its application will become more common.

Reference:
Patent; Payne, Andrew; Castro Pineiro, Jose Luis; Birch, Louise Michelle; Khan, Afzal; Braunton, Alan James; Kitulagoda, James Edward; Soejima, Motohiro; US2015/94328; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 23056-47-5, Adding some certain compound to certain chemical reactions, such as: 23056-47-5, name is 2-Bromo-4-methyl-5-nitropyridine,molecular formula is C6H5BrN2O2, 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 23056-47-5.

A mixture of NH4C1 (14.9 mmol) and iron powder (18.4 mmol) in H20 (5 mE) was stirred at 90 C. 2-bromo-4- methyl-5-nitropyridine (2.3 mmol) was added in portions. The mixture was stirred at 90 C. for 1 h and 15 mm. The reaction was stopped and extracted with EtOAc. The organic layer was dried (Na2SO4) and concentrated to yield the desired product.

According to the analysis of related databases, 23056-47-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GALAPAGOS NV; Menet, Christel Jeanne Marie; Mammoliti, Oscar; Blanc, Javier; Orsulic, Mislav; Roscic, Maja; (81 pag.)US9440929; (2016); B2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 97966-00-2, 5-Bromo-2,3-dichloropyridine, 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, COA of Formula: C5H2BrCl2N, blongs to pyridine-derivatives compound. COA of Formula: C5H2BrCl2N

To a solution of 5-bromo-2,3-dichloropyridine (29) (702 mg, 3.09 mmol) in THF (7 ml) was dropwise added isopropylmagnesium chloride lithium chloride complex (3.09 ml, 4.02 mmol) at 0 C. for 10 min. Then N-methoxy-N-methylacetamide (658 mul, 6.19 mmol) in THF (2 ml) was dropwise added to the reaction mixture at the same temperature and stirred at for 2 hrs. Then the reaction mixture was quenched with aqueous solution and extracted with ethyl acetate. The resulting organic layer was washed with brine, dried over Na2SO4 and concentrated in vacuo. The resulting product was chromatographed on silica gel eluting with a gradient of hexane/ethyl acetate (5-15%) to afford 232 mg of the desired product (30) in 40% yield as a white solid. 1H-NMR (DMSO-d6) delta: 8.91 (1H, s), 8.55 (1H, s), 2.65 (3H, s).

The synthetic route of 97966-00-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SHIONOGI & CO., LTD.; Kurose, Noriyuki; Iso, Yasuyoshi; Yamaguchi, Naoko; Shao, Bin; Tafesse, Laykea; Zhou, Xiaoming; Yu, Jianming; US9156830; (2015); B2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 14916-65-5, 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. 14916-65-5, name is 6-Nitropyridin-3-amine. A new synthetic method of this compound is introduced below.

To a solution of 6-nitro-pyridin-3-ylamine (50 mg, 0.33 mmol) in DMF (3 mL) was added NaH (60% in mineral oil, 25 mg, 0.66 mmol), and the mixture was stirred at r.t for 30 min. Then 5-bromo-2-methoxy-benzenesulfonyl chloride (86 mg, 0.3 mmol) was added and the mixture was stirred at 50 C overnight. TLC showed that the reaction was complete. The resultant was concentrated in vacuum to remove DMF. The residue was diluted with DCM (30 mL) and the mixture was washed with IN HC1 (30 mL x3) .The organic layer dried over Na2S04 and concentrated to dryness in vacuum. The residue was purified by silica gel column (PE/EtOAc, 1/1) to give 30 mg (yield: 26%) of 5-bromo-2-methoxy-N-(6-nitro-pyridin-3-yl)- benzenesulfonamide as a brown solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,14916-65-5, 6-Nitropyridin-3-amine, and friends who are interested can also refer to it.

Reference:
Patent; SANFORD-BURNHAM MEDICAL RESEARCH INSTITUTE; PINKERTON, Anthony, B.; DAHL, Russell; COSFORD, Nicholas, D.P.; MILLAN, Jose, Luis; WO2013/126608; (2013); 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.184416-83-9, name is 2,3-Dichloropyridin-4-amine, molecular formula is C5H4Cl2N2, molecular weight is 163.01, as common compound, the synthetic route is as follows.HPLC of Formula: C5H4Cl2N2

A mixture of tert-butyl ((l S)-l’-(3-iodo-l-(tetrahydro-2H-pyran-2-yl)-lH- pyrazolo[3,4-b]pyrazin-6-yl)-l,3-dihydrospiro[indene-2,4′-piperidin]-l-yl)carbamate (350.0 mg, 555.0 pmol, from Intermediate J), 2,3-dichloropyridin-4-amine (135.0 mg, 832.0 pmol, CAS 184416-83-9), XantPhos-Pd-G4 (47.6 mg, 55.4 pmol) and Cs2C03 (270.0 mg, 832.0 pmol) in PhMe (10 mL) was stirred at 100 C for 12 hours. The reaction mixture was concentrated and purified by silica gel column (EtOAc in petroleum ether = 0-30%) to give tert-butyl N-[(3S)-l’-{3-[(2,3-dichloropyridin-4-yl)amino]-l-(oxan-2-yl)-lH-pyrazolo[3,4- b]pyrazin-6-yl}-l,3-dihydrospiro[indene-2,4′-piperidin]-3-yl]carbamate (200.0 mg, 54% yield) as a yellow solid. LCMS m/z [M+H]+ = 665.1.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,184416-83-9, 2,3-Dichloropyridin-4-amine, and friends who are interested can also refer to it.

Reference:
Patent; RELAY THERAPEUTICS, INC.; D.E. SHAW RESEARCH, LLC; TAYLOR, Alexander, M.; LESCARBEAU, Andre; KELLEY, Elizabeth, H.; SHORTSLEEVES, Kelley, C.; WALTERS, W., Patrick; MURCKO, Mark, Andrew; MCLEAN, Thomas, H.; GUNAYDIN, Hakan; GIORDANETTO, Fabrizio; THERRIEN, Eric; (607 pag.)WO2019/183367; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 89364-04-5, 3-Bromo-4-nitropyridine, 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, Computed Properties of C5H3BrN2O2, blongs to pyridine-derivatives compound. Computed Properties of C5H3BrN2O2

Step 5: 5-(2,3-difluoro-4-(4-nitropyridin-3-yl)phenyl)-2-((1-phenyl-2,5,8,11,14-pentaoxahexadecan-16-yl)oxy)pyridine To a solution of 5-(2,3-difluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl)-2-((1-phenyl-2,5,8,11,14-pentaoxahexadecan-16-yl) oxy) pyridine (350 mg, 0.544 mmol) in dioxane/H2O (11 mL, 10/1, v/v) was added 3-bromo-4-nitropyridine (121 mg, 0.6 mmol), Na2CO3 (120 mg, 1.1 mmol) and Pd(PPh3)4 (63 mg). The mixture was stirred at 110 C. for 1h under N2. After the reaction, the mixture was extracted with ethyl acetate (20 mL) and washed with brine (30 mL). The organic solution was dried over anhydrous sodium sulfate and concentrated. The crude was purified by column chromatography on silica gel with PE/EA (1:3) to give the desired product (170 mg) as a yellow oil.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,89364-04-5, 3-Bromo-4-nitropyridine, and friends who are interested can also refer to it.

Reference:
Patent; Arvinas, Inc.; Crew, Andrew P.; Berlin, Michael; Flanagan, John J.; Dong, Hanqing; Ishchenko, Alexey; (559 pag.)US2018/125821; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 75279-39-9, N-(4-Aminopyridin-2-yl)acetamide, 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, Product Details of 75279-39-9, blongs to pyridine-derivatives compound. Product Details of 75279-39-9

Immediately add 45% HBF4 water to solid compound d obtained by rotary evaporation of the above solutionSolution (600mL, 10.8mo1),After stirring, the solid was completely dissolved and ethanol (200 mL) was added.Ice salt bath cooled to below -5C,Isoamyl nitrite (150 mL, 1.12 mol) was added dropwise.Control temperature does not exceed 0 C,And stir the reaction below 0C for 3h.After the reaction was completed, tetrahydrofuran (200 mL) was added.Cool to below 0C,Suction filtrationThe solid was washed twice with tetrahydrofuran (20 mL) and dried in a vacuum desiccator to obtain a solid compound e (213.25 g, 85.3%) with a purity of 96%.The diazonium fluoborate (250g, 1mo1) was put into a dry 1L triple reaction flask.Heat to 120C,Solid decomposition,White smoke emerged from the reaction flask.Continue heating to exhaust white smoke.Solid decomposition is complete.Prepare a 40% NaOH solution (300 mL)The solids on the condenser tube are washed into the reaction flask.Heat reflux,As the product is sublimated,The continuous condensation of solids on the condenserCollect the solids,Repeat the above operation,2-amino-4-fluoropyridine (70 g, 62.5%) was obtained,98% purity.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,75279-39-9, N-(4-Aminopyridin-2-yl)acetamide, and friends who are interested can also refer to it.

Reference:
Patent; Shanghai Lingkai Pharmaceutical Technology Co., Ltd.; Lu Qian; (7 pag.)CN107759515; (2018); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 902837-42-7, 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.902837-42-7, name is 7-Bromo-1H-pyrrolo[3,2-c]pyridine, molecular formula is C7H5BrN2, molecular weight is 197.032, as common compound, the synthetic route is as follows.

Sodium hydride (0.25 g, 6.2 mmol) is added under ice bath cooling to a mixture of 7-bromo-1H-pyrrolo[3,2-c]pyridine (0.8 g, 4.1 mmol) in DMF (10 ml). The mixture is stirred for 30 minutes before methyl iodide (0.25 ml, 4.1 mmol) is added. The mixture is warmed to RT and stirred for 17 h. The mixture is diluted with DCM and extracted with a saturated aqueous sodium hydrogencarbonate solution. The combined organic layers are dried over MgSO4 and concentrated in vacuo. The product is purified by RP HPLC. Yield: 0.61 g (71%). HPLC-MS: tR=0.88 min (METHOD-1).

Statistics shows that 902837-42-7 is playing an increasingly important role. we look forward to future research findings about 7-Bromo-1H-pyrrolo[3,2-c]pyridine.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; REISER, Ulrich; US2015/57286; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 823221-95-0, 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 823221-95-0, name is 5-Chloro-4-iodo-2-(trifluoromethyl)pyridine. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 5-Chloro-4-iodo-2-trifluoromethyl-pyridine (7.25 g, 23.6 mmol) in DMSO (70.0 mL) were added diethylmalonate (4.53 g, 28.3 mmol) and cesium carbonate (11.52 g, 35.3 mmol). The reaction mixture was stirred at 100C for 5 h. Reaction completion was confirmed by TLC. Upon cooling, the reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. Crude product was purified by flash column chromatography on silica gel eluting with 10-20% ethyl acetate/hexanes to yield diethyl 2-(5-Chloro-2-trifluoromethyl-pyridin-4-yl)-malonic acid diethyl ester 1. MS ESI/APCI calc’d. for C13H13CIF3NO4[M + H]+339.7, found 340.2.

According to the analysis of related databases, 823221-95-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME CORP.; SHAO, Pengcheng Patrick; YE, Feng; VACHAL, Petr; WO2015/94932; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1083057-12-8, Adding some certain compound to certain chemical reactions, such as: 1083057-12-8, name is tert-Butyl 3-(3-methylpyridin-2-yl)benzoate,molecular formula is C17H19NO2, 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 1083057-12-8.

Preparation of 2-(3-(tert-butoxycarbonyl)phenyl)-3-methylpyridine-1-oxide tert-Butyl-3-(3-methylpyridin-2-yl)benzoate (1.0 eq) was dissolved in EtOAc (6 vol). Water (0.3 vol) was added, followed by urea-hydrogen peroxide (3 eq). Phthalic anhydride (3 eq) was then added portionwise to the mixture as a solid at a rate to maintain the temperature in the reactor below 45 C. After completion of the phthalic anhydride addition, the mixture was heated to 45 C. After stirring for an additional 4 hours, the heat was turned off. 10% w/w aqueous Na2SO3 (1.5 eq) was added via addition funnel. After completion of Na2SO3 addition, the mixture was stirred for an additional 30 min and the layers separated. The organic layer was stirred and 10% wt/wt aqueous. Na2CO3 (2 eq) was added. After stirring for 30 minutes, the layers were allowed to separate. The organic phase was washed 13% w/v aq NaCl. The organic phase was then filtered and concentrated to afford crude 2-(3-(tert-butoxycarbonyl)phenyl)-3-methylpyridine-1-oxide (95%) that was used directly in the next step.

According to the analysis of related databases, 1083057-12-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Vertex Pharmaceuticals Incorporated; Verwijs, Marinus Jacobus; (75 pag.)US2016/324788; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem