Day: April 12, 2022

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. 59105-50-9, name is (5-Bromopyridin-3-yl)(phenyl)methanone, the common compound, a new synthetic route is introduced below. COA of Formula: C12H8BrNO

General procedure: Pd(PPh3)4 (17.3 mg, 0.015 mmol) was added to a solution of 3-benzoy-5-bromo pyridine(130.1 mg, 0.5 mmol) and aryl boronic acid (0.6 mmol) in MeOH (0.2 mL), toluene (0.8 mL),and 2 M Na2CO3 (0.2mL) under N2. The mixture was heated to 75 C for 2 h, and then cooledto room temperature and concentrated under reduced pressure. Water was added to theresidue and the aq. phase was extracted with DCM (3 × 5 mL). The combined organic layerswere washed with brine, dried over Na2SO4, and evaporated to obtain the crude product.Purification by column chromatography on silica gel afforded the desired product.

The synthetic route of 59105-50-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Fu, Yun; Sun, Jian; Molecules; vol. 24; 3; (2019);,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 49669-13-8, 2-Acetyl-6-bromopyridine, 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, Formula: C7H6BrNO, blongs to pyridine-derivatives compound. Formula: C7H6BrNO

A solution of l-(6~bromorhoyridin-2-yl)ethanone (5 g, 25.0 mmol) in diethyl ether (77 ml) at 00C was treated with methyl magnesium bromide (8.33 ml, 25.0 mmol). After 3 hours, water was added to quench excess methyl magnesium bromide, and then concentrated aqueous hydrogen chloride solution was added until two layers were obtained. The layers were separated and the aqueous layer was extracted with diethyl ether (3 x 50 mL). The combined organic layers were dried over sodium sulfate, filtered, and concentrated to yield the title compound. LRMS (APCI) calc’d for C8H1 jBrNO [M+H]+: 216, Found: 216.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,49669-13-8, 2-Acetyl-6-bromopyridine, and friends who are interested can also refer to it.

Reference:
Patent; MERCK & CO., INC.; MACHACEK, Michelle, R.; HAIDLE, Andrew; ZABIEREK, Anna, A.; KONRAD, Kaleen, M.; ALTMAN, Michael, D.; WO2010/11375; (2010); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 52334-51-7, 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.52334-51-7, name is 3-Amino-5-methylpyridin-2(1H)-one, molecular formula is C6H8N2O, molecular weight is 124.14, as common compound, the synthetic route is as follows.

(Reference Example 5-2) At room temperature, to a mixed solvent solution of 3-amino-5-methylpyridin-2-ol (4.03 g) in tetrahydrofuran (50 ml) and 1,2-dichloroethane (50 ml) were added tert-butyl 4-oxopiperidine–1-carboxylate (13.04 g), sodium triacetoxyborohydride (13.87 g) and acetic acid (3.75 ml), followed by heating at reflux for 16 hours. After the temperature was brought back to room temperature, 1 N aqueous sodium hydroxide solution was added, and extracted with chloroform. The organic layer was washed with saturated sodium chloride solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to afford tert-butyl 4-[(2-hydroxy-5-methylpyridin-3-yl)amino]piperidine-1-carboxylate (7.6 g). 1H NMR (400 MHz, CDCl3) delta 1.40-1.50 (m, 2H), 1.47 (s, 9H), 1.98-2.10 (m, 2H), 2.06 (s, 3H), 2.92-3.02 (m, 2H), 3.32-3.41 (m, 1H), 3.95-4.10 (m, 2H), 4.78-4.83 (m, 1H), 6.16 (s, 1H), 6.48 (s, 1H), 11.5-11.8 (br m, 1H).

The chemical industry reduces the impact on the environment during synthesis 52334-51-7, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Daiichi Sankyo Company, Limited; EP2471792; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1005785-85-2, 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. 1005785-85-2, name is 5-(tert-Butyl)picolinic acid, molecular formula is C10H13NO2, 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 carboxylic acid (80 mg, 0.45 mmol) and CDI (145 mg, 0.90 mmol) in DMF (4 mL) was stirred at rt for 0.5 h, followed by the addition of the amine (110 mg, 0.45 mmol) and Et3N (137 mg, 1.35 mmol) and the mixture was stirred at rt for 16 h. After diluted with water (5 mL), the mixture was extracted with EtOAc (5 mL x 2). The combined organics were concentrated in vacuo and the residue was purified by reverse phase chromatography (MeOH/H2O with 0.05% NH3.H2O as mobile phase) to afford the title compound (26 mg, yield 15%) as a yellow solid. ESI-MS (M+H)+: 400.2.1H NMR (400 MHz, CD3OD) : 8.77-8.74 (m, 2H), 8.06-8.03 (m, 2H), 7.92-7.95 (m, 2H), 7.54-7.51 (m, 2H), 6.86 (d, J = 4.0 Hz, 1H), 4.74 (s, 2H), 2.53 (s, 3H), 1.42 (s, 9H).

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 1005785-85-2, 5-(tert-Butyl)picolinic acid.

Reference:
Patent; BIOGEN IDEC MA INC.; SUNESIS PHARMACEUTICALS, INC.; HOPKINS, Brian T.; MA, Bin; CHAN, Timothy Raymond; KUMARAVEL, Gnanasambandam; MIAO, Hua; BERTOLOTTI-CIARLET, Andrea; OTIPOBY, Kevin; WO2015/89327; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1121056-94-7, 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. 1121056-94-7, name is 5-Nitro-3-(trifluoromethyl)pyridin-2-amine, molecular formula is C6H4F3N3O2, 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.

To a stirred solution of 5-nitro-3-(trifluoromethyl)pyridin-2-amine (2 g, 9.66 mmol) in dichloromethane (20 mL) was added DMAP (1.29 g, 10.62 mmol), Et3N (2.69 mL, 19.31 mmol) and acetyl chloride (0.758 mL, 10.62 mmol) at room temperature and the resulting reaction mixture was stirred for 1H. After completion of the reaction, reaction mixture was neutralized with aqueous (1 M) solution of potassium carbonate. Aqueous phase was extracted with ethyl acetate (20 mL x 3), combined organic layer was dried over anhydrous sodium sulphate and filtered. The filtrate was rotary evaporated and residue was purified by flash column chromatography (silica gel) to afford 1.1 g (46%) of the titled product as yellow solid. 1HNMR (400 MHz, DMSO-d6) U10.73 (s, 1H), 9.47 (d, J = 2.6 Hz, 1H), 8.84 (d, J = 2.6 Hz, 1H), 2.14 (s, 3H); ESI-MS (m/z) 249.80 (MH)

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 1121056-94-7, 5-Nitro-3-(trifluoromethyl)pyridin-2-amine.

Reference:
Patent; LUPIN LIMITED; KUKREJA, Gagan; IRLAPATI, Nageswara, Rao; JAGDALE, Arun, Rangnath; DESHMUKH, Gokul, Keruji; VYAVAHARE, Vinod, Popatrao; KULKARNI, Kiran, Chandrashekhar; SINHA, Neelima; PALLE, Venkata, P.; KAMBOJ, Rajender, Kumar; (366 pag.)WO2018/20474; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 84487-15-0, 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 84487-15-0, name is 2-Bromo-5-nitropyridin-4-amine. This compound has unique chemical properties. The synthetic route is as follows.

Step A: 5-Nitro-2-(2-trifluoromethyl-phenyl)-pyridin-4-ylamine 2-Bromo-5-nitropyridin-4-amine (561 mg, 2.57 mmol), Cs2CO3 (2.52 g, 7.72 mmol), (dppf)PdCl2.DCM (113 mg, 0.154 mmol), and 2-(trifluoromethyl)phenylboronic acid (636 mg, 3.35 mmol) were combined and flushed with Ar and anhydrous DME (24 mL) was added. H2O (8 mL) was added via syringe and the resulting mixture was stirred at 85 C. for 18 h. The resulting mixture was cooled to room temperature and diluted with EtOAc (30 mL) and the resulting solution was washed with brine (30 mL). The aqueous phase was extracted with EtOAc (3*25 mL) and the combined extracts were dried over MgSO4 and filtered. The solvent was removed under reduced pressure and the residue was chromatographed on a 40-g SiO2 pre-packed column eluting with 0:1-2:3 EtOAc/hexanes to yield 5-nitro-2-(2-trifluoromethyl-phenyl)-pyridin-4-ylamine. 1H-NMR (400 MHz, CDCl3) delta: 9.17 (s, 1H), 7.70 (d, J=7.8 Hz, 1H), 7.56 (t, J=7.1 Hz, 1H), 7.49 (t, J=7.5 Hz, 1H), 7.40 (d, J=7.6 Hz, 1H), 7.00 (br. s., 2H), 6.71 (s, 1H). Mass Spectrum (LCMS, ESI pos.): Calculated for C12H8F3N3O2: 284.1 (M+H); Measured: 284.1.

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 84487-15-0, 2-Bromo-5-nitropyridin-4-amine.

Reference:
Patent; PLAYER, Mark R.; Calvo, Raul; Chen, Jinsheng; Meegalla, Sanath; Parks, Daniel; Parsons, William; Ballentine, Scott; Branum, Shawn; US2011/218197; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 6515-09-9, 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.6515-09-9, name is 2,3,6-Trichloropyridine, molecular formula is C5H2Cl3N, molecular weight is 182.4351, as common compound, the synthetic route is as follows.

To Compound 12 (5.47 g, 30 mmol) were added nitric acid (30 mL) and concentrated sulfuric acid (24 mL) at room temperature, and the reaction mixture was warmed up to 100 C. and stirred with heating for approximately 8 hours. The reaction mixture was added to iced water, the resulting mixture was stirred. The precipitated solid was filtered to obtain Compound 13 (6.82 g, 64.7%). Compound 13; Method B [0817] LC/MS retention time=2.03 min.

Statistics shows that 6515-09-9 is playing an increasingly important role. we look forward to future research findings about 2,3,6-Trichloropyridine.

Reference:
Patent; SHIONOGI & CO., LTD.; Tamura, Yuusuke; Kojima, Eiichi; Ikemoto, Hidaka; Hinata, Yu; US2015/203450; (2015); 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.3279-76-3, name is 6-Methylpyridin-2(1H)-one, molecular formula is C6H7NO, molecular weight is 109.13, as common compound, the synthetic route is as follows.Recommanded Product: 3279-76-3

To a solution of 6-methyl-pyridin-2-ol (2.5 g, 0.023 mol) in CH2CI2 (10 mL) at r. t. , under N2, were added AG2CO3 (6 g, 1.5 eq. ) and Mel (5,6 mL, 4 eq). The solution was stirred at r. t. for 4 days, then AG2CO3 was filtered and washed with CH2CI2, and the organic layer was evaporated to dryness. The crude product was purified by flash chromatography (silica gel, EtOAc/cHex 2: 8) to give the title compound (1.9 mg, 67%) as a white solid. NMR (‘H, CDCl3) : 8 7.4 (t, 1H), 6.6 (d, 1H), 6.5 (d, 1H), 3.8 (s, 3H), 2.4 (s, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,3279-76-3, 6-Methylpyridin-2(1H)-one, and friends who are interested can also refer to it.

Reference:
Patent; SB PHARMCO PUERTO RICO INC; NEUROCRINE BIOSCIENCES INC; GLAXO GROUP LIMITED; WO2004/62665; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 55052-27-2, 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.55052-27-2, name is 6-Chloro-1H-pyrrolo[2,3-b]pyridine, molecular formula is C7H5ClN2, molecular weight is 152.581, as common compound, the synthetic route is as follows.

To a solution of 7n (2.7 mmol, 410 mg), tetrabutylammonium hydrogen sulfate (3 mol%, 27 mg) and benzene sulfonyl chloride(3.3 mmol, 583 mg) in DCM (15 mL) placed at ice bath was added1N NaOH solutions (3.0 mL). The resulting mixture was stirred atroom temperature for 8 h. Water (30 mL) was added cautiously tothe reaction, and the mixture was extracted with DCM (15mL 3).The combined organic phase was washed with saturated NaCl (aq)for three times, dried over anhydride sodium sulfate and concentratedunder reduced vacuum. The crude product (14a) was directlyused in next step.

Statistics shows that 55052-27-2 is playing an increasingly important role. we look forward to future research findings about 6-Chloro-1H-pyrrolo[2,3-b]pyridine.

Reference:
Article; Liu, Bin; Yuan, Xia; Xu, Bo; Zhang, Han; Li, Ridong; Wang, Xin; Ge, Zemei; Li, Runtao; European Journal of Medicinal Chemistry; vol. 170; (2019); p. 1 – 15;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 16727-47-2 , The common heterocyclic compound, 16727-47-2, name is 2,6-Bis(benzyloxy)-3-bromopyridine, molecular formula is C19H16BrNO2, 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.

A mixture of 1-Methyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyridin-2- one 44-3 (200mg, 1.30 mmol), 2,6-bis(benzyloxy)-3-bromopyridine (16-1) (481 mg, 1.30 mmol) and K2CO3 (539 mg, 3.90 mmol) in dioxane / H2O (2ml, 4:1, v/v) was thoroughly degassed under argon followed by addition of Pd2(dba)3 (119 mg, 130 mumol) and tri-tertiarybutylphosphine tetrafluoroborate (75.4 mg, 260 mumol) and finally heating at 100 0C overnight. The reaction mixture was filtered over Celite, the filtrate was concentrated and the crude residue was purified by flash column chromatography to afford 2′,6′-bis(benzyloxy)-1-methyl-[3,3′-bipyridin]-2(1H)-one (44-4) (120 mg, 301 mumol, 23.2 %). LC MS: ES+ 399.2

The synthetic route of 16727-47-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; C4 THERAPEUTICS, INC.; PHILLIPS, Andrew, J.; NASVESCHUK, Chris, G.; HENDERSON, James, A.; LIANG, Yanke; HE, Minsheng; LAZARSKI, Kiel; VEITS, Gesine, Kerstin; VORA, Harit, U.; (794 pag.)WO2017/197046; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem