Pyridine-derivatives

Reference of 17117-13-4, Adding some certain compound to certain chemical reactions, such as: 17117-13-4, name is 2-Bromo-4-ethoxypyridine,molecular formula is C7H8BrNO, 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 17117-13-4.

Preparation 36 To a suspension of 2-bromo-4-ethoxypyridine (879 mg), 3-nitrophenylboronic acid (944 mg) and tetrakis(triphenylphosphine)-palladium (251 mg) in 1,2-dimethoxyethane (20 ml) was added 2M aqueous solution of sodium carbonate (5.66 ml). The mixture was stirred at 90 C. for 8 hours under a nitrogen atmosphere, then cooled to room temperature and diluted with ethyl acetate. The organic layer was separated, washed with water and brine and dried over sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by column chromatography (silica gel 40 g, 25% ethyl acetate in n-hexane) to give 3-(4-ethoxypyridin-2-yl)nitrobenzene (887 mg). 1H-NMR (CDCl3): delta1.49(3H,t,J=7.0 Hz), 4.18(2H,q,J=7.0 Hz), 6.83(1H,dd,J=5.7 Hz,2.4 Hz), 7.29(1H,d,J=2.4 Hz), 7.63(1H,t,J=8.0 Hz), 8.2-8.4(2H,m), 8.54(1H,d,J=5.7 Hz), 8.81(1H,t,J=2.0 Hz)

According to the analysis of related databases, 17117-13-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Fujisawa Pharmaceutical Co., Ltd.; US6521643; (2003); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1062368-71-1 ,Some common heterocyclic compound, 1062368-71-1, molecular formula is C9H7BrN2O2, 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.

Methyl 4-bromopyrazolo [1,5 -a]pyridine-3 -carboxylate (100 mg, 0.39 mmol), Pd(OAc)2 (5.3 mg, 0.024 mmol), BNAP (22 mg, 0.035 mmol) and Cs2CO3 (192 mg, 0.59 mmol) were placed in a pressure vial. The reaction mixture was degassed (3x vacuum and argon), then toluene (2 mL) and morpholine (0.044 mL, 0.51 mmol) were added. Thereaction mixture was degassed again, and then was stirred at 120 C for 3 h. After cooled to rt, the reaction was filtered through a pad of CELITE, and the solvent was removed. The crude product was purified by reverse phase chromatography to provide Intermediate 109 (74 mg, 72%) as a light tan solid. ?H NMR (400MHz, CDC13) oe 8.46 (s, 1H), 8.43 (d, J=6.6 Hz, 1H), 7.31 (d, J=7.7 Hz, 1H), 7.05 (t, J7.2 Hz, 1H), 4.11 – 4.04(m, 4H), 3.94 (s, 3H), 3.40 – 3.27 (m, 4H). LC-MS(ESI) m/z: 262.0 [M+H].

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1062368-71-1, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; LADZIATA, Vladimir; GLUNZ, Peter W.; HU, Zilun; WANG, Yufeng; (0 pag.)WO2016/10950; (2016); 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. 83766-88-5, name is 2-(tert-Butoxy)pyridine, the common compound, a new synthetic route is introduced below. name: 2-(tert-Butoxy)pyridine

Carboxylic acid (0.2 g, 1.64 mmol), tert-butoxypyridine (0.33 g, 2.21 mmol) and boron trifluoride diethyl etherate (0.31 g, 2.21 mmol) in dry PhCH3 (2 mL) were added to a 20-ml vial. The reaction mixture was then allowed to stir at room temperature for 30 min before quenching with anhydrous NaHCO3. The reaction mixture was diluted with ethyl acetate (30 mL), then washed with water (20 mL), followed by brine (20 mL). The organic layer was dried over anhydrous sodium sulfate and carefully concentrated under reduced pressure. The resulting residue was then purified by flash column chromatography on silica gel with 0:4 to 1:4 dichloromethane/hexane as eluent to yield the desired product 5a as a colorless oil.

The synthetic route of 83766-88-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; La, Minh Thanh; Kim, Hee-Kwon; Tetrahedron; vol. 74; 27; (2018); p. 3748 – 3754;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 639091-75-1, Adding some certain compound to certain chemical reactions, such as: 639091-75-1, name is Methyl 2-(Boc-amino)isonicotinate,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 639091-75-1.

A 500mL round bottomed flask was charged with methyl 2-((tert-butoxycarbonyl)amino)isonicotinate (5.95 g, 23.6 mmol) and suspended in methanol (1 18 ml). To this stirring solution was added 3.0M potassium hydroxide (23.6 mL, 70.8 mmol). The flask was vented and heated to 50 C for 10 minutes. LCMS analysis showed clean and complete conversion of starting material to a single product consistent with the desired product by mass (m/z=237[M-H]-). The mixture was cooled to room temperature and then 1.ON HCl was added to give a white precipitate. The solid was collected by filtration and dried overnight to give 2-((tert- butoxycarbonyl)amino)isonicotinic acid, HCl (5.2 g, 18.93 mmol, 80 % yield). 1H NMR (400 MHz, DMSO-d6) delta ppm 13.64 (1 H, br. s.), 10.06 (1 H, s), 8.39 (1 H, d, J=5.27 Hz), 8.30 (1 H, s), 7.42 (1 H, dd, J=5.02, 1.51 Hz), 1.48 (9 H, s).

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. 639091-75-1, Methyl 2-(Boc-amino)isonicotinate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; SCHMITZ, William D.; DEBENEDETTO, Mikkel V.; KIMURA, S. Roy; WO2013/3298; (2013); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 73101-79-8, 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. 73101-79-8, name is 5-Ethoxy-6-methylpyridin-2-amine, molecular formula is C8H12N2O, 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.

b) The product from part a) (19.0 g) was added dropwise to 5M sodium hydroxide solution (29 ml) and water (100 ml) keeping the temperature below 15 C. This solution was then added quickly to the solution of 5-ethoxy-6-methyl-pyridin-2-amine (20.0 g) in 4M hydrochloric acid (40 ml) and water (200 ml). This mixture was stirred at ambient temperature for 2 hours then filtered to give a solid which was recrystallized from IMS/water to give ethyl 2-(5-ethoxy-6-methylpyridin-2-ylaminomethylene)propionate, m.p. 118-122 C.

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 73101-79-8, 5-Ethoxy-6-methylpyridin-2-amine.

Reference:
Patent; The Boots Company PLC; US5464781; (1995); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 98197-88-7, 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. 98197-88-7, name is 2-(Hydroxymethyl)-4-nitropyridine, molecular formula is C6H6N2O3, 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.

A solution of (4-nitropyridin-2-yl)methanol (100 mg, 0.65 mmol) in ethanol (4 mL) was treated with a solution of sodium ethoxide in ethanol (21% by weight, 0.31 mL, 0.83 mmol) and the reaction mixture was heated under reflux for 48 h. Water (10 mL) was added, the mixturewas neutralized with concentrated aq. hydrochloric acid and ethanol was removed by evaporation in vacuo. More water (20 mL) was added and the mixture was extracted with DCM (4 x 30 mL). Extracts were dried (MgSO4) and concentrated to give (4-ethoxypyridin-2- yl)methanol W (73 mg, 73%) as a red oil, used without purification.LCMS (method A): 2.07 (154.1, MH).

According to the analysis of related databases, 98197-88-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; REDAG CROP PROTECTION LTD; URCH, Christopher John; BUTLIN, Roger, John; CHRISTOU, Stephania; BOOTH, Rebecca, Kathryn; (122 pag.)WO2019/77345; (2019); 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. 60290-23-5, name is 1H-Pyrrolo[3,2-c]pyridin-4-amine, molecular formula is C7H7N3, 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. SDS of cas: 60290-23-5

Example 96-Preparation of tert-butyl 4-(bis (tert-butoxycarbonyl) amino)-1H-pyrrolo [3,2-c]pyridine-1-carboxylate (Compound 59) Under nitrogen, compound 58 (1.2 g, 9.02 mmoles) was dissolved in a mixture of acetonitrile (10 mL) and dichloromethane (20 mL) at room temperature. DMAP (4.4 g, 36 mmoles) was added and the mixture was cooled to 0 deg C. After stirring at 0 deg C. for 30 minutes, di-tert-butyl dicarbonate (8.6 mL, 35.7 mmoles) was added. The reaction was stirred at room temperature for 24 hours after which, it was concentrated to dryness. The residue was diluted with ethyl acetate (50 mL) and washed with saturated aqueous potassium bisulfate solution (25 mL). The layers were separated and the organic phase was dried over anhydrous sodium sulfate, filtered and concentrated to dryness. The residue was purified on silica gel (10% ethyl acetate in hexane) giving compound 59 (2.73 g, 70% yield).

With the rapid development of chemical substances, we look forward to future research findings about 60290-23-5.

Reference:
Patent; Levy, Daniel E.; Abarzua, Patricio; (51 pag.)US2017/362235; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 57883-25-7, 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 57883-25-7 as follows.

A suspension of 3-bromo-2-ethoxypyridine (Preparation 1 1 , 28.69 g, 142.0 mmol), bis(pinacolato)diboron (43.3 g, 170.5 mmol), and potassium acetate (41 .8 g, 425.9 mmol) in DMSO (100 mL) was degassed with nitrogen and [1 ,1 ‘- bis(diphenylphosphinoferrocene]dichloro palladium (II) (5.8 g, 7.93 mmol) was added and the reaction mixture was stirred for 6 hours at 95 C. The reaction mixture was filtered through a pad of Arbocel which was washed with ethyl acetate (500 mL). The filtrate was concentrated in vacuo and the crude material was purified by silica gel column chromatography eluting with 50% ethyl acetate in cyclohexane to afford the title compound as a red oil (34.4g, 74%). 1H NMR (400MHz, CDCl3): delta ppm 1 .35 (s, 12H), 1 .39 (m, 3H), 4.37 (m, 2H), 6.81 (m, 1 H), 7.89 (m, 1 H), 8.19 (m, 1 H). LCMS Rt = 3.27 minutes MS m/z 250 [MH]+

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,57883-25-7, its application will become more common.

Reference:
Patent; PFIZER LIMITED; STORER, Robert, Ian; SWAIN, Nigel, Alan; WO2013/93688; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 79055-63-3, 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. 79055-63-3, name is 2-Chloro-6-methylpyridin-4-amine. A new synthetic method of this compound is introduced below.

To a flask was added 2-chloro-4-(trifluoromethyl)-pyrimidine (1.50 g, 8.22 mmol), 2-chloro-6-methylpyridin-4-amine (1.17 g, 8.22 mmol), palladium acetate (0.18 g, 0.82 mmol), Xantphos (0.95 g, 1.64 mmol), and cesium carbonate (5.36 g, 16.44 mmol) followed by 1,4-dioxane (16.44 mL). The mixture was stirred at 100 C for 2 hours. The reaction was cooled to room temperature and was diluted with ethyl acetate and aqueous sodium bicarbonate solution and extracted with ethyl acetate. The combined organic fractions were washed with brine, dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (0-50% ethyl acetate/hexanes) to afford N- (2-chloro-6-methylpyridin-4-yl)-4-(trifluoromethyl)pyrimidin-2-amine as a pale yellow solid. MS ESI calcd. for C11H9CIF3N4 [M + H]+ 289, found 289. XH NMR (500 MHz, DMSO-d6) delta 10.82 (s, 1H), 8.96 (d, J= 5.0 Hz, 1H), 7.78 (d, J= 1.5 Hz, 1H), 7.50 (d, J= 1.5 Hz, 1H), 7.48 (d, J= 5.0 Hz, 1H), 2.37 (s, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,79055-63-3, 2-Chloro-6-methylpyridin-4-amine, and friends who are interested can also refer to it.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MERCK CANADA INC.; ANTHONY, Neville, J.; ANDRESEN, Brian, M.; NORTHRUP, Alan, B.; CHILDERS, Kaleen, K.; DONOFRIO, Anthony; MILLER, Thomas, A.; LIU, Yuan; MACHACEK, Michelle, R.; WOO, Hyun Chong; SPENCER, Kerrie, B.; ELLIS, John Michael; ALTMAN, Michael, D.; ROMEO, Eric, T.; GUAY, Daniel; GRIMM, Jonathan; LEBRUN, Marie-Eve; ROBICHAUD, Joel, S.; WANG, Liping; DUBOIS, Byron; DENG, Qiaolin; WO2014/176210; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 709652-82-4, 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.709652-82-4, name is 2-Amino-5-bromonicotinonitrile, molecular formula is C6H4BrN3, molecular weight is 198.0201, as common compound, the synthetic route is as follows.

To a microwave reaction vessel were added 4-(tert- butoxycarbonylamino)phenylboronic acid (180 mg, 0.759 mmol), 5-bromo-3-cyano- 2-aminopyridine (170.0 mg, 0.858 mmol), 1,4-dioxane (3.5 mL) and 2M aqueous sodium carbonate (0.94 mL, 1.88 mmol). Argon gas was bubbled through the solution for 5 min, then tetrakis(triphenylphosphine) palladium(O) (40.0 mg, 0.035 mmol) was added and the vial was sealed and heated in a microwave reactor for 20 min at 170 C. The mixture was partitioned between EtOAc (10 mL) and saturated sodium bicarbonate (10 mL) The aqueous layer was separated and extracted with ethyl acetate (3 x 10 mL). The combined organic layers were washed with brine (10 mL), dried over MgS04, filtered and concentrated under reduced pressure to give an oil which was purified by silica gel flash chromatography, eluting with 25-100% EtOAc in hexanes. The purified material was dissolved in DCM (4 mL), excess TFA (2 mL) added and the mixture was stirred at rt for 4 h. The mixture was concentrated to dryness, then EtOAc (8 mL), saturated NaHC03 (8 mL) and 1 M aqueous NaOH (1 mL) were added. After confirming basic pH, the layers were shaken and separated and the aqueous layer was extracted with EtOAc (2 x 5 mL). The combined extracts were dried over MgS04, filtered and concentrated under reduced pressure to give 2- amino-5-(4-aminophenyl)nicotinonitrile (113.9 mg, 71%) as a solid, which was sufficiently pure for the next step. LC-MS (ESI) m/z 2 (M +H)+.

Statistics shows that 709652-82-4 is playing an increasingly important role. we look forward to future research findings about 2-Amino-5-bromonicotinonitrile.

Reference:
Patent; AMBIT BIOSCIENCES CORPORATION; ABRAHAM, Sunny; HOLLADAY, Mark, W.; LIU, Gang; XU, Shimin; WO2011/22473; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem