Day: August 20, 2021

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. 113118-81-3, name is 5-Bromonicotinaldehyde, the common compound, a new synthetic route is introduced below. Quality Control of 5-Bromonicotinaldehyde

To a solution of 5-bromonicotinaldehyde (XXXVII) (2.0 g, 10.8 mmol, 1 eq) in MeOH (20 mL) was added NaBH4 (2.4 g, 64.9 mmol, 6 eq) and the reaction mixture was stirred at room temperature for 3 h. The mixture was concentrated in vacuo and the residue was diluted in water (15 mL), the aqueous phase was extracted with DCM (10 mL x 3). The combined organic layers were dried over Mg504, filtered and concentrated in vacuo to afford (5- bromopyridin-3-yl)methanol (XLIV) (1.8 g, 9.57 mmol, 90.0% yield) as a colorless oil. ?H NMR (CDC13, 500 MHz) ppm 4.73 (s, 2H), 7.90 (s, 1H), 8.47 (s, 1H), 8.57 (s, 1H). ESIMS found for C6H6BrNO mlz 188.0 (M+H).

The synthetic route of 113118-81-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SAMUMED, LLC.; KC, Sunil Kumar; WALLACE, David Mark; CAO, Jianguo; CHIRUTA, Chandramouli; MARAKOVITS, Joseph Timothy; BOLLU, Venkataiah; HOOD, John; (307 pag.)WO2017/23989; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 59281-14-0, 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 59281-14-0 as follows.

(B) 2-(Chloromethyl)-5-(phenylmethoxy)-4(1H)pyridinone, monohydrochloride A suspension of 2-(hydroxymethyl)-5-(phenylmethoxy)-4(1H)-pyridinone (3 g, 12.99 mmole) in chloroform (15 ml) was cooled to 0 under argon and treated with thionyl chloride (6.1 ml, 83.62 mmole). Within several minutes, a homogeneous solution was obtained. After stirring an additional 5 minutes, a cream colored solid precipitated. The cooling bath was removed and the mixture was heated at reflux for 45 minutes. The mixture was cooled to 0 and the white precipitate was filtered, washed with chloroform and hexane and dried in vacuo. The yield of the title compound was 3.65 g.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,59281-14-0, its application will become more common.

Reference:
Patent; E. R. Squibb & Sons, Inc.; US4743685; (1988); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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 6959-48-4, name is 3-(Chloromethyl)pyridine hydrochloride. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 3-(Chloromethyl)pyridine hydrochloride

General procedure: DMF (5-10 mL/mmol). K2CO3 (10 equiv) was added and the suspensionstirred for 15 min. Then, 3-(chloromethyl) pyridiniumchloride (1.1 equiv) was added and the reaction mixture was stirredfor 48 h at room temperature. The suspension was diluted withH2O and extracted with EtOAc. The combined organic phases werewashed with H2O and brine, dried over magnesium sulfate and thesolvent was removed in vacuo. The crude products were purifiedby column chromatography [Cyclohexane/EtOAc, 3:1 4.2.2.2 tert-Butyl N-(4-methoxyphenylsulfonyl)-N-(3-pyridylmethyl)-2-amino-4-fluorobutanoate (S)-Enantiomer ((S)-14): Yield: 1512 mg (85%), greenish, viscous oil. 1H NMR (300 MHz, CDCl3): delta 1.35 (s, 9H), 1.86 (m, 1H), 2.22 (ddt, 2JH,H = 13.6 Hz, 3JH,H = 9.7 Hz, 3JH,H = 6.0 Hz, 1H), 3.86 (s, 3H), 4.19-4.45 (m, 2H), 4.36 (d, 2JH,H = 16.1 Hz, 1H), 4.49 (dd, 3JH,H = 7.7 Hz, 3JH,H = 6.6 Hz, 1H), 4.69 (d, 2JH,H = 16.2 Hz, 1H), 6.96 (dm, 3JH,H = 8.9 Hz, 2H), 7.25 (dd, 3JH,H = 7.9 Hz, 3JH,H = 4.8 Hz, 1H), 7.77 (dm, 3JH,H = 8.9 Hz, 2H), 7.82 (dm, 3JH,H = 8.4 Hz, 1H), 8.51 (s, 1H), 8.53 (s, 1H) ppm. 13C NMR (75 MHz, CDCl3): delta 27.7 (q), 31.8 (dt, 2JC,F = 20.5 Hz), 47.3 (t), 55.6 (q), 57.0 (dd, 3JC,F = 4.3 Hz), 80.1 (dt, 1JC,F = 166.3 Hz), 82.5 (s), 114.1 (d), 123.4 (d), 129.6 (d), 131.3 (s), 132.9 (s), 136.3 (d), 149.1 (d), 149.4 (d), 163.0 (s), 169.0 (s) ppm. 19F NMR (282 MHz, CDCl3): delta -221.4 (ddt, 2JH,F = 46.9 Hz, 3JH,F = 28.3 Hz, 3JH,F = 22.8 Hz) ppm. HRMS (ESI+): C21H27N2O5S+H+, calcd 439.1703, found: 439.1701; C21H27N2O5S + Na+, calcd 461.1522, found: 461.1526; (C21H27N2O5S)2+H+, calcd 877.3328, found: 877.3320; (C21H27N2O5S)2 + Na+, calcd 899.3147, found: 899.3146. MS (ESI+, daughter ion experiment): m/z (%) 439 (15) [M++H+], 383 (100) [439-C4H8], 171 (5) [C7H7O3S+], 167 (10) [383-C7H7O3S-CO2H], 92 (3) [C6H6N+]. Optical rotation (c 1.001, CHCl3): [alpha]58920 = +34.1, [alpha]57820 = +35.5, [alpha]54620 = +41.1, [alpha]43620 = +74.5, [alpha]36520 = n.d.

With the rapid development of chemical substances, we look forward to future research findings about 6959-48-4.

Reference:
Article; Behrends, Malte; Wagner, Stefan; Kopka, Klaus; Schober, Otmar; Schaefers, Michael; Kumbhar, Sadhana; Waller, Mark; Haufe, Guenter; Bioorganic and Medicinal Chemistry; vol. 23; 13; (2015); p. 3809 – 3818;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 10366-35-5, 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. 10366-35-5, name is 2-Chloronicotinamide, molecular formula is C6H5ClN2O, 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 an aqueous solution of Na2Se2 (prepared from selenium metal (1.00 g, 12.66 mmol) and NaBH4 (434 mg, 11.47 mmol) in 60 ml distilled water) was added a solution of 2-chloro-3-nicotinamide (2.00 g, 12.77 mmol) with stirring under a nitrogen atmosphere. The reaction mixture was refluxed for 2 h with stirring. After cooling to room temperature, product was extracted with a chloroform-methanol (3:1 ratio) mixture. The organic phase was separated, washed with sodium bicarbonate solution followed by water, dried over anhydrous sodium sulphate, and filtered. The filtrate was concentrated under vacuum and the residue was column chromatographed with chloroform-methanol (90:10) mixture. The solution on evaporation afforded yellow powder (yield 216 mg, 8%; due to degradation during column purification product yield was significantly reduced), m.p. 126-128 C. Anal. for C12H10N4O2Se2; Calcd: C, 36.02; H, 2.52; N, 14.00%. Found C, 34.64; H, 2.73; N, 13.47%. UV-vis (in MeOH) (lambdamax in nm): 326, 402. IR in KBr (upsilon cm-1): 3250 (NH2), 1671 (CO). 1H NMR (dmso-d6) delta: 7.28 (d, d, 6 Hz, CH-5, py); 8.35, 7.84 (NH2); 8.16 (d, 7.5 Hz, py); 8.49 (d, 5 Hz, py); 13C{1H} NMR (dmso-d6) delta: 119.7, 128.1 (C-Se),135.5, 151.5, 160.5 (C-3, py); 168.2 (CO). 77Se{1H} NMR (dmso-d6) delta: 525 ppm. Mass (m/z): 400 (M+).

According to the analysis of related databases, 10366-35-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Parashiva Prabhu; Phadnis, Prasad P.; Wadawale, Amey P.; Indira Priyadarsini; Jain, Vimal K.; Journal of Organometallic Chemistry; vol. 713; (2012); p. 42 – 50;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 951624-83-2, 5-(Trifluoromethyl)nicotinonitrile, 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, HPLC of Formula: C7H3F3N2, blongs to pyridine-derivatives compound. HPLC of Formula: C7H3F3N2

(Reference Example 117) 6-Chloro-5-(trifluoromethyl)pyridine-3-carbonitrile[0812] Urea hydrogen peroxide (0.815 g, 8.66 mmol) and trifluoroacetic anhydride (1.15 mL, 8.24 mmol) were added to a solution of 5-(trifluoromethyl)pyridine-3-carbonitrile (compound described in the pamphlet of WO2009/42694, 0.71 g, 4.12 mmol) in dichloromethane (10 mL), and the mixture was stirred overnight. A 10% sodium thiosulfate aqueous solution was added to the reaction solution, followed by extraction with dichloromethane twice. The organic layer was washed with brine and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography [elute: hexane/ethyl acetate = 88/12 – 0/100 (gradient)] to obtain a product. [0814] A solution of the obtained product in phosphoryl chloride (10 mL) was stirred at 70C for 2 hours and further for 2 hours under reflux. The reaction solution was poured to ice, followed by extraction with dichloromethane twice. Combined organic layers were washed with brine and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography [elute: hexane/ethyl acetate = 99/1 – 90/10 (gradient)] to obtain the title compound (62 mg, yield: 7%).[0815] 1H-NMR (CDCl3) delta: 8.86 (1H, d, J = 2 Hz), 8.28 (1H, d, J = 2 Hz).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,951624-83-2, 5-(Trifluoromethyl)nicotinonitrile, and friends who are interested can also refer to it.

Reference:
Patent; Daiichi Sankyo Company, Limited; KOBAYASHI, Hideki; OHKAWA, Nobuyuki; TAKANO, Daisuke; KUBOTA, Hideki; ONODA, Toshio; KANEKO, Toshio; ARAI, Masami; TERASAKA, Naoki; EP2862861; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 16478-52-7 ,Some common heterocyclic compound, 16478-52-7, molecular formula is C7H7NO3, 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.

starting from 1.6 g of 3-methoxy-2-pyridinecarboxylic acid there was obtained t-butyl [2-(3-methoxypyridine-2-carboxamido)ethyl]carbamate, m.p. 115°;

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. 16478-52-7, 3-Methoxypicolinic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Hoffmann-La Roche Inc.; US4764522; (1988); A;,
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. 625-92-3, name is 3,5-Dibromopyridine, molecular formula is C5H3Br2N, 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. Recommanded Product: 3,5-Dibromopyridine

In diethyl ether (42.0 mL) was dissolved 3,5-dibromopyridine (1.00 g, 4.22 mmol). n-Butyllithium (2.76 mol/L solution in n-hexane, 1.61 mL, 4.43 mmol) was added dropwise at -78 C., and the mixture was stirred at the same temperature for 30 minutes. Further, DMF (0.98 mL, 12.7 mmol) was added and the mixture was stirred for 3 hours allowing the temperature to rise slowly to room temperature. A saturated aqueous ammonium chloride solution and water were added to the reaction mixture. Extraction with ethyl acetate, washing with saturated brine and drying over anhydrous sodium sulfate were performed. After filtration, the solvent in the filtrate was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate 7/3) to give 5-bromonicotinaldehyde (314 mg, 40%).

With the rapid development of chemical substances, we look forward to future research findings about 625-92-3.

Reference:
Patent; Kyowa Hakko Kirin Co., Ltd.; Fukuda, Yuichi; Kanai, Toshimi; Nakasato, Yoshisuke; Kimpara, Keisuke; US2013/65905; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 875781-15-0, 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. 875781-15-0, name is 5-Bromo-2-fluoronicotinaldehyde. A new synthetic method of this compound is introduced below.

To a stirred solution of 5-bromo-2-fluoronicotinaldehyde (XV) (250 g, 1.23mol, 1.0 eq) in EtOH (2.50 L) was added hydrazine hydrate (221 g, 4.41 mol, 3.6 eq) at 25C. The reaction was then heated to 7580C and stirred for 12 h. The solvent was removed under reduced pressure at 45C. The residual crude solid was triturated in water (750 mL) and EtOH (250 mL). The resultant suspension was filtered and washed with ethanol to give 5-bromo-1H- pyrazolo[3,4-bjpyridine (XVI) (135 g, 0.68 mol, 55.4% yield) as yellowish solid which was used directly for the next step without further purification. ESIMS found for C6H4BrN3 mlz 199.1 (M+H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,875781-15-0, 5-Bromo-2-fluoronicotinaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; SAMUMED, LLC.; KC, Sunil Kumar; WALLACE, David Mark; CAO, Jianguo; CHIRUTA, Chandramouli; HOOD, John; (242 pag.)WO2017/23981; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 67815-54-7 ,Some common heterocyclic compound, 67815-54-7, molecular formula is C5H2F3N, 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.

INTERMEDIATE 27 3 ,5 -Difluoro-4-(3 -iodo- 1 H-pyrazol- 1 -vDpyridine To a solution of 3-iodopyrazole (0.70 g, 3.61 mmol), in DMSO (15.1 mL) was added sodium hydride (60% in oil, 0.159 g, 3.97 mmol) and stirred for 0.5 h before 3,4,5- trifluoropyridine (0.48 g, 3.61 mmol) was added. The reaction mixture was stirred at 90 C for 3 h. This was quenched by the addition of water and extracted with EtOAc. The combined organic extracts were washed with water and brine, dried over MgS04 and concentrated in vacuo. The crude mixture was purified by flash chromatography (ISCO Combiflash, 40 g, 0-30 % EtOAc in hexanes) to give 3,5-difluoro-4-(3-iodo- lH-pyrazol-l-yl)pyridine, as a white solid. LCMS calc. = 307.94; found = 307.92 (M+H)+. 1H NMR (500 MHz, CDC13): delta 8.53 (s, 2 H); 7.65 (dd, J= 3.9, 2.3 Hz, 1 H); 6.72 (d, J= 2.5 Hz, 1 H).

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. 67815-54-7, 3,4,5-Trifluoropyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MOCHIDA PHARMACEUTICAL CO., LTD.; SMITH, Cameron, James; TAN, John, Qiang; ZHANG, Ting; BALKOVEC, James; GREENLEE, William, John; GUO, Liangqin; XU, Jiayi; CHEN, Yi-heng; CHEN, Yili; CHACKALAMANNIL, Samuel; HIRABAYASHI, Tomokazu; NAGASUE, Hiroshi; OGAWA, Kouki; WO2014/120346; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 82454-61-3, Adding some certain compound to certain chemical reactions, such as: 82454-61-3, name is 5-Ethynylpyridin-2-amine,molecular formula is C7H6N2, 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 82454-61-3.

To a stirring suspension of 310 mg (0.719 mmol) of 3-azido-N-(5-tert-butyl-3- methanesulfonylamino-2-methoxy-phenyl)-4-methyl-benzamide in 2 mL of EtOH and 2 mL of water was added dropwise 4M NaOH until the mixture became homogeneous. A solution of 142 mg (0.719 mmol) of sodium ascorbate in 0.5 mL of water was added, followed by 100 mg (0.719 mmol) 2-amino-4-ethynyl pyridine in 1 mL of EtOH. Finally 0.72 mL of 0.1 M CuS04 was added, and the resulting mixture was stirred vigorously for 14 h. The mixture was then diluted with 40 mL of water and HOAc was added until a precipitate formed and the pH was about 6. The precipitate was filtered and washed with water and hexanes. The solids were chromatographed (0-5percent MeOH/0.5percent NH40H in CH2C12) to provide 321 mg (0.584 mmol ; 81percent) of the title compound. ESI MS nilz 548 [C27H3lN704S-H]-.

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. 82454-61-3, 5-Ethynylpyridin-2-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BOEHRINGER INGELHEIM PHARMACEUTICALS, INC.; WO2005/90333; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem