Month: April 2022

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

Synthetic Route of 851386-40-8, Adding some certain compound to certain chemical reactions, such as: 851386-40-8, name is 4-Chloro-2,5-difluoropyridine,molecular formula is C5H2ClF2N, 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 851386-40-8.

4-chloro-2,5-difluoropyridine E2 (1 .00 equivalents), 4-cyano-phenylboronic acid (1 .20 equivalents), Pd2(dba)3 (0.02 equivalent), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (SPhos) (0.08 equivalents) and tribasic potassium phosphate (2.50 equivalents) are stirred under nitrogen atmosphere in a dioxane/water mixture (ratio of 10:1 ) at 1 10 C for 20 h. To the reaction mixture Celite and active carbon are added and stirred at 1 10C for 15 min. Subsequently the reaction mixture is hot filtered and the residue washed with dioxane. The reaction mixture is poured into 200 mL of a saturated sodium chloride solution and extracted with ethyl acetate. The combined organic phases are washed with saturated sodium chloride solution, dried over MgSC>4 and the solvent is evaporated under reduced pressure. The crude product obtained is purified by recrystallization in cyclohexane and the product obtained as solid. (0422) Instead of a boronic acid a corresponding boronic acid ester may be used.The synthesis of Z3 is carried out according to AAV1-1, wherein 4-chloro-2,5-difluoropyridine E2 reacts with 3-cyano-phenylboronic acid ester. eneral procedure for synthesis AAV2-1:

According to the analysis of related databases, 851386-40-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CYNORA GMBH; ESTEBAN, Alhama Arjona; (133 pag.)WO2018/189356; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 54903-86-5, 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. 54903-86-5, name is 3-Bromopyridine-2,6-diamine. A new synthetic method of this compound is introduced below.

Preparation of N-(6-amino-5-bromo(2-pyridyl))(2-fluorophenyl)carboxamide (61): A solution of 3-bromo-2,6-diaminopyridine (60) (564 mg, 3 mmol), triethyl amine (0.54 ml) in DCM (6 ml)/THF (4 ml) was cooled down to -78 C. A solution of 2-fluorobenzoyl chloride (362 mul, 3.03 mmol) in 2 ml DCM was added dropwise within 10 min. The resulting reaction mixture was stirred at -78 C. for 1 h before slowly warm up to r.t. After stirred at r.t. for 3 h, the reaction quenched with aq NaHCO3 solution. 200 ml EA were added. Org. phase was washed with brine, dried over sodium sulfate, concentrated. The light yellow solid residue was triturated with DCM (ca. 15 ml), filtered and dried to give 530 mg N-(6-amino-5-bromo(2-pyridyl))(2-fluorophenyl)carboxamide (61) as white solid. (purity>95%, yield: 57%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,54903-86-5, 3-Bromopyridine-2,6-diamine, and friends who are interested can also refer to it.

Reference:
Patent; CalciMedica, Inc.; US2011/263612; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 866775-18-0, 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 866775-18-0, name is Methyl 3-amino-6-bromo-5-(trifluoromethyl)picolinate. This compound has unique chemical properties. The synthetic route is as follows.

Intermediate A: 3-Amino-6-bromo-5-trifluoromethyl-pyridine-2-carboxylic acid3-Amino-6-bromo-5-trifluoromethyl-pyridine-2-carboxylic acid methyl ester (1.40 g, 4.68 mmol) was suspended in MeOH (15 ml); Sodium hydroxide (2.0 M aqueous solution) (14.04 ml, 28.1 mmol) was added and the suspension was stirred at RT overnight. The mixture was concentrated in vacuo and the resulting residue was dissolved in water (100 ml) and then acidifed by the addition of 5.0M HCl(aq). The product was extracted into ethyl acetate (2×75 ml) and the combined organic extracts were washed with water (50 ml), brine (25 ml), dried (MgSO4) and concentrated in vacuo to afford the title product as a yellow solid. 1H-NMR: [400 MHz, DMSO-d6, deltaH 13.24 (1H, br s, CO2H), 7.74 (1H, s, ArH), 7.17 92H, br s ArNH2). m/z 285.1, 287.1 [M+H]+

According to the analysis of related databases, 866775-18-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NOVARTIS AG; US2011/230483; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 53636-68-3, 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. 53636-68-3, name is 3-Amino-5-chloropicolinic acid. A new synthetic method of this compound is introduced below.

3-Amino-5-chloropyridine-2-carboxylic acid (Int 2, 2 g, 11.6 mmol) was dissolved in NMP (100 mL) together with 1-amino-2-methyl-propan-2-ol (CAS: 2854-16-2, 1.14 g, 12.8 mmol), triethylamine (3.56 mL, 25.6 mmol) and HATU (4.87 g, 12.8 mmol). The resulting mixture was stirred at room temperature overnight. Next, the mixture was diluted with water and extracted with EtOAc. The organic fractions were combined, concentrated and the resulting crude residue was purified by column chromatography (petroleum ether/EtOAc 95/5 to 50/50) to give 3-amino-5-chloro-pyridine-2-carboxylic acid (2-hydroxy-2-methyl-propyl)-amide.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,53636-68-3, its application will become more common.

Reference:
Patent; ABBVIE S.A.R.L.; GALAPAGOS NV; ALTENBACH, Robert, J.; COWART, Marlon, D.; DE MUNCK, Tom, Roger Lisette; DROPSIT MONTOVERT, Sebastien Jean, Jacques Cedric; GFESSER, Gregory, A.; KELGTERMANS, Hans; MARTINA, Sebastien, Laurent Xavier; VAN DER PLAS, Steven, Emiel; WANG, Xueqing; (300 pag.)WO2016/193812; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem