Category: pyridine-derivatives

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. 639091-75-1, name is Methyl 2-(Boc-amino)isonicotinate, the common compound, a new synthetic route is introduced below. Safety of Methyl 2-(Boc-amino)isonicotinate

Step 1. Preparation of methyl 2-[(tert-butoxycarbonyl(methyl)amino]isonicotinate A slurry of methyl 2-[(tert-butoxycarbonyl)amino]isonicotinate (5.0 g, 2.0E1 mmol) in DMF (75 mL) was cooled to ?0 C. (ice/NaCl) and treated with a 1.0 M solution of sodium hexamethyldisilazane in THF (24 mL, 24 mmol) dropwise over 25 min to afford a clear, yellow/brown solution. The reaction mixture was stirred for 30 min at 0 OC and treated with methyl iodide (1.4 mL, 22 mmol). The reaction mixture was stirred for 20 min, the cold bath was removed, and the reaction mixture stirred at rt for 2 h; HPLC/LC MS indicated complete conversion to product. The reaction mixture was cooled to ?0 C. and the reaction was quenched by the addition of saturated aqueous NH4Cl (25 mL). The mixture was allowed to warm to rt and was extracted with Et2O (3*50 mL). The combined organics were washed with saturated aqueous NaHCO3 (1*50 mL) and 10% aqueous LiCl (2*50 mL), dried (Na2SO4), and concentrated in vacuo to afford a bright yellow oil with precipitate. The crude material was further dried on high vacuum overnight to afford the crude title compound as a light colored solid/yellow oil (5.29 g). MS (ESI+) for C13H18N2O4LC m/z 267.1 (M+H)+; HPLC retention time: 3.78 min (Method B).

The synthetic route of 639091-75-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; EXITHERA PHARMACEUTICALS INC.; Chrusciel, Robert A.; Gadwood, Robert C.; Hayward, Neil J.; Melnick, Michael J.; Navia, Manuel A.; Poel, Toni J.; Stassen, Frans L.; Stewart, Catherine A.; US2015/225389; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 16727-47-2, 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.16727-47-2, name is 2,6-Bis(benzyloxy)-3-bromopyridine, molecular formula is C19H16BrNO2, molecular weight is 370.2398, as common compound, the synthetic route is as follows.

To the stirred solution of (2,6-dibenzyloxy-3-bromo-pyridine) 43-1 (5 g, 13.50 mmol)in dry THF (30 mL), 2.5 M BuLi in Hexane (7.08 g, 20.26 mmol) was added at -78C under inertatmosphere and stirred for 1 hour at rt. After that, dry DMF (1.5 mL) was added to the reactionmixture dropwise at -78C and stirring was continued for further 2 hours at room temperature. After completion of reaction, as evidenced from TLC, reaction mixture was quenched withsaturated ammonium chloride solution. The aqueous phase was extracted with ethyl acetate.Combined organic layer was separated, dried over anhydrous sodium sulfate and concentratedunder vacuum. The crude reaction mass was purified by column chromatography to obtain5 desired compound 43-2 (2,6-dibenzyloxypyridine-3-carbaldehyde) (2.8 g, 8.77 mmol, 64.92%yield) as sticky solid. ES (M+H): 320.

Statistics shows that 16727-47-2 is playing an increasingly important role. we look forward to future research findings about 2,6-Bis(benzyloxy)-3-bromopyridine.

Reference:
Patent; C4 THERAPEUTICS, INC.; PHILLIPS, Andrew, J.; NASVESCHUK, Christoper, G.; HENDERSON, James, A.; LIANG, Yanke; HE, Minsheng; DUPLESSIS, Martin; CHEN, Chi-Li; (791 pag.)WO2018/237026; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference 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.

Triethylamine (4.13 g, 3 niL, 40.8 mmol, 4 eq) is added to a solution of 6-chloro- nicotinonitrile (1.38 g, 10 mmol, leq), (S)-2-methyl- piperazine (1.0Og, 10 mmol, leq) in DMF (15 niL), and the resulting solution is stirred at rt for 14 h. A white precipitate of triethylamine hydrochloride forms in the course of the reaction. Water (15 mL) and EtOAc (100 mL) are added, the organic layer is separated, dried over sodium sulfate and concentrated under reduced pressure to a white residue. The solid is further dried under high vacuum to yield the desired product as a white solid (1.4 g, 69%). 1H NMR (400 MHz, CHLOROFORM-cf) delta ppm 8.38 (s, 1 H), 7.58 (d, J=9.60 Hz, 1 H), 6.59 (d, J=9.09 Hz, 1 H), 4.19 – 4.31 (m, 2 H), 3.08 – 3.15 (m, 1 H), 2.92 – 3.04 (m, 1 H), 2.81 – 2.91 (m, 2 H), 2.57 – 2.65 (m, 1 H), 1.15 (d. J=6.32 Hz, 3 H).

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; NOVARTIS AG; WO2008/110611; (2008); A1;,
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. 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. Computed Properties of C6H5F3N2

The compound of Example 36A(1 g, 6.2 mmol), trifluoroacetic anhydride (1.30 g, 6.2 mmol) and pyridine(0. 54 g, 6.8 mol) are dissolved in tetrahydrofuran (20ml) under an argon atmosphere. The solution is cooled to-78 C with stirring and lithium diisopropylamide (3.0 ml of a 2 M solution in THF/heptane, 6.0 mmol) is added dropwise. The reaction mixture is allowed to warm to room temperature, and then stirred at room temperature overnight. The reaction is quenched with water and extracted with ethyl acetate (3 x 100 ml). The ethyl acetate phase is washed with brine, dried with magnesium sulphate monohydrate, filtered and concentrated to give a yellow oil. The oil is purified by flash chromatography on silica gel with cyclohexane/ethyl acetate mixtures as eluent. Yield: 1.05 g (66%of th.) HPLC (method 8): Rt = 4.23 min MS(EI) :m/z = 259(M+H)”IHh R (300 MHz, DMSO-d6) :8 = 8. 46 (s, 1H) ; 8.84 (s, 1H) ; 9.10 (s, 1H) ;11. 80 (s,1H) ppm.

With the rapid development of chemical substances, we look forward to future research findings about 112110-07-3.

Reference:
Patent; BAYER HEALTHCARE AG; WO2004/20412; (2004); 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.39774-26-0, name is 2-Bromo-6-phenylpyridine, molecular formula is C11H8BrN, molecular weight is 234.09, as common compound, the synthetic route is as follows.Application In Synthesis of 2-Bromo-6-phenylpyridine

To a solution of 21-1 (2.70 g, mixture from previous step) in tetrahydrofuran (50 mL) cooled to -78 C. under nitrogen, n-butyllithium (2.5 M in hexanes, 5.8 mL, 14.5 mmol) was added dropwise. The mixture was stirred for 45 minutes then N,N-dimethylformamide (1.80 mL, 23 mmol) was added. The mixture was stirred at -78 C. for 1 hour, warmed to room temperature, quenched with water, and extracted with ethyl acetate. The organic layer was washed three times with water, once with brine, dried over sodium sulfate, filtered and concentrated. The residue was purified by silica gel column chromatography, eluting with 2.5% followed by 5% ethyl acetate in hexanes to give 6-phenylpicolinaldehyde (21-2, 1.24 g) as a yellow oil.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,39774-26-0, 2-Bromo-6-phenylpyridine, and friends who are interested can also refer to it.

Reference:
Patent; Aviara Pharmaceuticals, Inc.; Biediger, Ronald J.; Benish, Michele A.; Hardy, Lindsay Bonner; Boyd, Vincent A.; Market, Robert V.; Thrash, Thomas P.; Young, Brandon M.; (83 pag.)US2018/312523; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1201676-03-0, 4,6-Dichloro-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-1-one, 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, Application In Synthesis of 4,6-Dichloro-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-1-one, blongs to pyridine-derivatives compound. Application In Synthesis of 4,6-Dichloro-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-1-one

A mixture of 4,6-dichloro-2,3-dihydro-pyrrolo[3,4-c]pyridin-1-one (1.19 g, 5.87 mmol), triethylamine (2.97 g, 29.3 mmol), and crude trifluoroacetic acid salt of piperidine-4- carboxylic acid isobutyl amide [obtained by stirring 4-isobutylcarbamoyl-piperidine-1- carboxylic acid te/f-butyl ester (2.63 g, 8.80 mmol) in dichloromethane (20 mL) and trifluoroacetic acid (6 mL) for 1.5 hours, then removing solvents by rotary evaporation] in dioxane (10 mL) is heated in a 75 mL sealed tube at 120 0C for 68 h. Filtration of room temperature mixture does not lead to separation of regioisomers. The filtrate is concentrated down to dryness by rotary evaporation, dissolved into ethyl acetate, and then washed with water and brine. The organic layer is dried over sodium sulfate, filtered and concentrated down to dryness by rotary evaporation. This residue is then combined with solids from first filtration and eluted through a silica gel column (80:20 ethyl acetate / heptane, then 100% ethyl acetate, then 95:5 ethyl acetate / methanol). The more polar regioisomer (TLC solvents: 90:10 ethyl acetate / methanol) is concentrated down to dryness by rotary evaporation, then treated with a small amount of methanol. The pink solid is isolated by filtration (0.647 g, 1.84 mmol, 31 %). MS(ESI) m/z 351.20 (M+1 ). 1H NMR (400 MHz, DMSOd6) delta ppm 9.00 (s, 1 H), 7.79 (t, J=5.81 Hz, 1 H), 6.84 (s, 1 H), 4.54 (s, 2 H), 4.19 (d, J=13.39 Hz, 2 H), 3.09 – 2.92 (m, 2 H), 2.86 (dd, J=6.57, 6.06 Hz, 2 H), 2.48 – 2.36 (m, 1 H), 1.79 – 1.71 (m, 2 H), 1.71 – 1.52 (m, 3 H), 0.82 (d, J=6.82 Hz, 6 H).

The synthetic route of 1201676-03-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; WO2009/150230; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 179687-79-7, Adding some certain compound to certain chemical reactions, such as: 179687-79-7, name is 2-((2-Chloro-4-nitrophenoxy)methyl)pyridine,molecular formula is C12H9ClN2O3, 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 179687-79-7.

Preparation of 3-chloro-4-(2-pyridylmethoxy)aniline from the nitrobenzene product of Example 1 was accomplished with catalytic hydrogenation using platinum on carbon. A typical hydrogenation was done using 6 volumes of THF, 2% by weight of 5% Pt/C (50% water wet), at 25 psi and at 25-30 C. for approximately 4-6 hours. The reaction is slightly exothermic and the temperature will rise to about 30-35 C. Cooling is necessary to maintain the temperature below 30 C. As a specific example, a mixture of 3-chloro-4-(2-pyridylmethoxy)nitrobenzene (0.15 kg, 0.57 mole) and 2% (w/w) of 5% Pt/C (6.0 g) in tetrahydrofuran (0.90 L) was hydrogenated at 25 psi for at least 5 hours. The mixture was filtered through a celite pad and washed with tetrahydrofuran (0.60 L). The filtrate was distilled to a volume of about 0.75 L and ethanol (1.12 L) was added. Distillation was continued to a volume of about 0.75 L and ethanol (2.85 L) was added. The mixture may be used ?as is? in the step of Example 3 below. ; Performing the hydrogenation in isopropyl alcohol (IPA), methanol (MeOH), or ethanol (EtOH) may result in the product being contaminated with late eluting impurity that partially precipitates out on standing in solution. It was found that performing the hydrogenation in a solvent where both the product and starting material are soluble, such as tetrahydrofuran (THF), resulted in greater product purity and required much less solvent. Thus, THF is a preferred solvent for this step. Experimental results showing the effect of different reaction conditions are shown in Table 2. For the larger scale runs, the first aniline intermediate was not isolated (?NI?) before proceeding with the next step. TABLE 2 Hydrogenation to Form First Aniline Intermediate 5% Scale (g) Pt/C** Solvent Vol Time (h) Yield (%) 2.0 1 IPA 50 3 79.6 18 2.0 5 EtOH 60 3100* 10 1 THF 10 4 94.5 7 10 1 EtOH 10 3 95.6 30 1.05 THF 6.5 12 96.3 14 100 2 THF 6 4.5 97.1 400 2 THF 6 4 NI 500 2 THF 6 4 NI 100 2 THF 6 5 NI 150 2 THF 6 5 NI 7 *Solid impurities noted after reaction completion. **percent by weight of starting material.

According to the analysis of related databases, 179687-79-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; WYETH; US2006/270668; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 896722-51-3, name is 6-Methyl-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine, the common compound, a new synthetic route is introduced below. HPLC of Formula: C14H12N2O2S

A solution of 50% NaOH (0.573 g) was added to N-protected 6-methyl-7-azaindole (0.390 g, 1.43 mmol) in Ethanol (10 mL). After refluxed for 8 h, the mixture was concentrated and was extracted with CHCl3. The organic layer was washed with water and dried. The solvent was evaporated in vacuo and the residue was purified on a silica gel column eluting with EtOAc/hexane (1:3) to give 6-methyl-1H-pyrrolo[2,3-b]pyridine (0.148 g, 78%).

The synthetic route of 896722-51-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hsieh, Hsing-Pang; Chao, Yu-Sheng; Liou, Jing-Ping; Chang, Jang-Yang; Tung, Yen-Shih; US2006/148801; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 946002-90-0, 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.946002-90-0, name is (S)-1-(5-Bromopyridin-2-yl)pyrrolidin-3-ol, molecular formula is C9H11BrN2O, molecular weight is 243.1, as common compound, the synthetic route is as follows.

(R)-5-Bromo-2-[3-(2,6-dichloro-4-methyl-phenoxy)-pyrrolidin-l-yl]-pyridine. ADDP (11.7 g, 45.4 mmol) was added to a sol. of compound Gl (8.82 g, 36.3 mmol) and 2,6-dichloro-/?-cresol (7.37 g, 40.0 mmol) in toluene (200 mL). The mixture was degassed with nitrogen for 5 min, and PBu3 (85%, 15.8 mL, 46.2 mmol) was added. The mixture was heated rapidly to 100 0C, and stirred at this temperature for 2 h. The mixture was allowed to cool to rt, and was diluted with heptane (200 mL). The mixture was filtered, and the filtrate was evaporated under reduced pressure. Purification of the residue by FC (EtO Ac/heptane 1 :7) yielded a crude title compound that was diluted with CH2Cl2. This mixture was washed with aq. IM NaOH. The org. layer was dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Drying the residue under high vacuum yielded the pure title compound (13.5 g, 93%). LC-MS: tR = 0.92 min; ES+: 402.98.

The chemical industry reduces the impact on the environment during synthesis 946002-90-0, I believe this compound will play a more active role in future production and life.

Reference:
Patent; ACTELION PHARMACEUTICALS LTD; WO2007/88514; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 695-98-7, 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. 695-98-7, name is 2,3,5-Trimethylpyridine, molecular formula is C8H11N, 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.

EXAMPLE 1 Bis(bis(trimethylsilyl)amido)bis(2,3,5-collidine)magnesium A 100-mL Schlenk flash was charged with bis(bis(trimethylsilyl)amido)bis(tetrahydrofuran)-magnesium (0.200 g, 0.460 mmol), a magnetic stir bar, and benzene (40 mL). 2,3,5-collidine (0.12 g, 0.91 mmol) was then added to this solution. The mixture was stirred for 18 h at room temperature. The volatile components were removed at reduced pressure to afford a yellow-orange solid. This solid was extracted into hexane (10 mL) and the resultant solution was filtered through a 2-cm pad of Celite.(R).. The filtrate was cooled to -20° C. for 18 h to afford colorless blocks of 1 (0.18 g, 66percent). Spectroscopic and analytical data for 1: mp 72°-73° C.; IR (Nujol, cm-1) 1249 (s), 1211 (m), 1148 (m), 1021 (s), 973 (s), 887 (s), 841 (s), 782 (s), 738 (s), 725 (s), 661 (s), 610 (s), 537 (s); 1 H NMR (C6 D6, delta) 8.39 (s, 2,3,5-collidine C-H), 6.63 (s, 2,3,5-collidine C-H), 2.43 (s, 2,3,5-collidine CH3), 1.81 (s, 2,3,5-collidine CH3), 1.69 (s, 2,3,5-collidine CH3), 0.33 (s, Si(CH3)3); 13 C{1 H} NMR (C6 D6, ppm) 154.32 (s, 2,3,5-collidine C-CH3), 147.00 (s, 2,3,5-collidine C-H), 139.41 (s, 2,3,5-collidine C-H), 132.00 (s, 2,3,5-collidine C-CH3), 131.26 (s, 2,3,5-collidine C-CH3), 22.04 (s, 2,3,5-collidine C-CH3), 18.62 (s, 2,3,5-collidine C-CH3), 17.45 (s, 2,3,5-collidine C-CH3), 5.87 (s, Si (CH3)3); Anal. Calcd for C28 H58 MgN4 Si4: C, 57.25; H, 9.95; N, 9.54. Found: C, 56.25; H, 10.00; N, 9.61.

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 695-98-7, 2,3,5-Trimethylpyridine.

Reference:
Patent; Wayne State University; US5892083; (1999); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem