Category: pyridine-derivatives

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 22282-70-8, name is 2-Fluoro-4-iodopyridine. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 2-Fluoro-4-iodopyridine

A solution of 2-fluoro-4-iodopyridine (10.00 g, 43.50 mmol) and ammonia (10 mL) in DMSO (20 mL) was stirred at 100 C for 40 h.Water (100 mL) was added to the reaction solution, and a solid was precipitated. The brown solid compound 10a (8.62 g, 90%) was obtained by filtration

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, 22282-70-8, 2-Fluoro-4-iodopyridine.

Reference:
Patent; JACOBIO PHARMACEUTICALS CO., LTD; MA, CUNBO; GAO, PANLIANG; CHU, JIE; WU, XINPING; WEN, CHUNWEI; KANG, DI; BAI, JINLONG; PEI, XIAOYAN; (171 pag.)TW2019/25186; (2019); A;,
Pyridine – Wikipedia,
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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.849068-61-7, name is 5-Bromo-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid, molecular formula is C8H5BrN2O2, molecular weight is 241.04, as common compound, the synthetic route is as follows.Application In Synthesis of 5-Bromo-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid

To a solution of 5-bromo-lH-pyrrolo [2,3-b] pyridine-3-carboxylic acid (600 mg, 2.49 mmol)Of N, N-dimethylformamide (20 mL)To the solution was added 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride (1.44 g, 7.43 mmol)1-hydroxybenzotriazole (1.01 g, 7.46 mmol) and2-isopropylamine (1.27 mL, 14.90 mmol),Stir overnight at room temperature.Saturated brine (20 mL) was added,Dichloromethane (15 mL x 3)Dried over anhydrous sodium sulfate, the solvent was removed,The concentrate was subjected to column chromatography (eluent: petroleum ether / ethyl acetate (v / v) = 5/1) to give the product as360 mg of a brown solid, yield: 51.3%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,849068-61-7, 5-Bromo-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Liu Bing; Huang Jiuzhong; Zheng Changchun; Zhang Yingjun; Ouyang Luo; Mao Hongfen; Nie Biao; Xu Juan; Chen Hongfen; (137 pag.)CN106336413; (2017); A;,
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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.Computed Properties of C6H4BrN3

To a solution of 2-amino-5-bromonicotinonitrile (1.4 equiv.) in toluene and ethanol (2.5:1) was added N-(4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan- 2-yl)phenyl)-3-(trifluoromethyl)benzamide (1.0 equiv.), Pd(PPh3)4 (0.1 equiv.) and aqueous potassium carbonate (3M, 3.0 equiv.). The reaction was heated in the microwave at 120 C for 40 min. The organic layer was separated and concentrated to dryness under vacuo. The residue was dissolved in DMSO and purified via reverse phase HPLC. The pure fractions were lyophilized to give N-(3-(6-amino-5-cyanopyridin-3-yl)-4-methylphenyl)-3- (trifluoromethyl)benzamide as the TFA salt in 48% yield. 1H NMR (400 MHz, DMSOd6) G 10.45 (s, 1H), 8.30 (s, 1H), 8.25 (d, J=2.0, 1H), 8.23 (d, J=2.0, 1H), 7.97 (d, J=8.0, 1H), 7.95 (d, J=4.0, 1H), 7.79 (t, J=8.0, 1H), 7.72 (dd, J=8.0, 2.0, 1H), 7.61 (d, J=4.0, 1H), 7.30 (d, J=12.0, 1H), 2.23 (s, 3H). LCMS (m/z) (M+H) = 397.1, Rt = 0.91 min.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,709652-82-4, 2-Amino-5-bromonicotinonitrile, and friends who are interested can also refer to it.

Reference:
Patent; NOVARTIS AG; BARSANTI, Paul Andrew; BURGER, Matthew T.; LOU, Yan; NISHIGUCHI, Gisele A.; POLYAKOV, Valery Rostislavovich; RAMURTHY, Savithri; SUBRAMANIAN, Sharadha; TAFT, Benjamin R.; TANNER, Huw Rowland; WAN, Lifeng; (180 pag.)WO2016/38583; (2016); A1;,
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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.1254473-66-9, name is 1-(3,5-Dichloropyridin-4-yl)ethanol, molecular formula is C7H7Cl2NO, molecular weight is 192.04, as common compound, the synthetic route is as follows.Computed Properties of C7H7Cl2NO

(30eq) was added to 30 ml of anhydrous THF and 327 mg (3.0 eq) of 60% NaH was added. After 30 min of activation, 400 mg of the starting material 17 was added and the reaction was complete after 12 hours of refluxing. Water and acetic acid The combined organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was dried to give brown oil 18 (420 mg) in 57.3% yield.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1254473-66-9, 1-(3,5-Dichloropyridin-4-yl)ethanol, and friends who are interested can also refer to it.

Reference:
Patent; SICHUAN BAILI PHARMACEUTICAL CO LTD; WU, YONG; ZHU, YI; HAI, LI; WANG, YIXI; LI, JIE; (23 pag.)CN105906621; (2016); A;,
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Reference of 97966-00-2 ,Some common heterocyclic compound, 97966-00-2, molecular formula is C5H2BrCl2N, 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.

To 5-bromo-2,3-dichloropyridine (29) (11.7 g, 51.6 mmol) was added HBr (5M in AcOH) (51.6 ml, 258 mmol) at room temperature. Then the reaction mixture was heated to 70 C. After being stirred for 7 hrs at 70 C., the reaction mixture was diluted with ethyl acetate, quenched with H2O and extracted with ethyl acetate. The resulting organic layer was washed with 1M NaOH, dried over over Na2SO4 and concentrated in vacuo. The residue was recrystallized from hexane-ethyl acetate to afford 11.2 g of the desired product (41) in 80% yield as a white solid. 1H-NMR (DMSO-d6) delta: 8.55 (1H, s), 8.49 (1H, s).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,97966-00-2, its application will become more common.

Reference:
Patent; SHIONOGI & CO., LTD.; Kurose, Noriyuki; Iso, Yasuyoshi; Yamaguchi, Naoko; Shao, Bin; Tafesse, Laykea; Zhou, Xiaoming; Yu, Jianming; US9156830; (2015); B2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 89809-63-2, 5-Methoxypicolinonitrile, 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, 89809-63-2, blongs to pyridine-derivatives compound. Safety of 5-Methoxypicolinonitrile

General procedure: To a solution of diisopropylamine (170 muL, 1.2 eq.) in dry THF (2 mL) in a flame dried round bottom flask under argon at 0 C was added n-butyllithium (690 muL, 1.6 M in hexanes, 1.1 eq.), and the reaction mixture was stirred at this temperature for 15 minutes. It was then cooled to -78 C and a solution of ketone (1) (1 mmol) in THF (2 mL) slowly added. Stirring at -78 C was continued for a further 30 minutes and methyl chlorosulfate (100 muL, 1.1 eq.) was then added. After stirring at -78 C for 30 minutes, the reaction was quenched with an aqueous saturated ammonium chloride solution (5 mL). The mixture was then extracted with dichloromethane (3 x 5 mL), the combined organic phases were dried with anhydrous magnesium sulfate and the solvent evaporated under vacuum affording the desired alpha-chloroketone 2.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,89809-63-2, its application will become more common.

Reference:
Article; Silva, Saul; Maycock, Christopher D.; Tetrahedron Letters; vol. 59; 13; (2018); p. 1233 – 1238;,
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.52538-09-7, name is 2,3-Dimethyl-3H-imidazo[4,5-c]pyridine, molecular formula is C8H9N3, molecular weight is 147.18, as common compound, the synthetic route is as follows.Product Details of 52538-09-7

To a solution of 2,3-dimethyl-3H-imidazo[4,5-c]pyridine (0.31 g, 2.14 mmol) in 3.5 ml 1,4-dioxine, selenium dioxide (356 mg, 3.21 mmol) was added and the mixture was heated by microwave under 1500C for 30 minutes. The mixture was filtered and the solvent was removed in vacuo. The residue purified using silica gel chromatography (0% to 10% MeOH/CH2CI2) to yield 3-methy|-3H-imidazo[4,5-c]pyridine-2-carbaldehyde (0.15 g); GC-MS 161.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,52538-09-7, 2,3-Dimethyl-3H-imidazo[4,5-c]pyridine, and friends who are interested can also refer to it.

Reference:
Patent; PFIZER PRODUCTS INC.; WO2008/12622; (2008); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 137520-99-1 ,Some common heterocyclic compound, 137520-99-1, molecular formula is C9H9Cl2NO2, 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.

To a mixture of 2,6-dichloro-3-methylisonicotinic acid ethyl ester (10.0 g, 42.7 mmol), Example 7E and acetic acid (2.69 g, 44.9 mmol) in carbon tetrachloride (147 ml.) are added lambda/-bromosuccinimide (8.36 g, 47.0 mmol) and then benzoyl peroxide (1.03 g, 4.27 mmol). The mixture is stirred in oil bath at 60 0C under heat lamp for 5 h. The mixture is then cooled to room temperature. About half of the solvent is removed by rotary evaporation. The white succinimide solid is removed by filtration. The overweight filtrate (17 g for a theoretical 13.4 g, 42.7 mmol) is concentrated under reduced pressure and used as a crude immediately for the next step. MS(ESI) m/z 313.99. 1H NMR (400 MHz1CDCI3) delta ppm 7.72 (s, 1 H), 4.99 (s, 2 H), 4.48 (q, J=7.16 Hz, 2 H), 1.46 (t, J=7.07 Hz, 3 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. 137520-99-1, Ethyl 2,6-dichloro-3-methylisonicotinate, other downstream synthetic routes, hurry up and to see.

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

Electric Literature of 1187322-51-5, 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. 1187322-51-5, name is 6-Amino-5-iodonicotinonitrile, molecular formula is C6H4IN3, 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.

1.2 g 5-[4-(6-trimethylsilanyl-hex-5-ynyl)-piperazin-1-yl]-benzofuran-2- carboxylic acid amide, 500 mg beta-amino-delta-iodo-nicotinonitrile, 0.1 g lithium chloride, 0.8 g sodium carbonate and 0.1 g 1,1′-bis(diphenyl- phosphino)ferrocenedichloropalladium- (II) dichloromethane adduct were dissolved in 50 ml DMF and heated for 12 h. The black suspension was poured on 50 ml water and extracted with ethyl acetate. After the usual extraction and purification procedure 20 mg of fawn amorphous solid 5-{4-[4-(5-cyano-1 H-pyrrolo[2,3-b]pyridine-3-yl)-butyl]- piperazin-1-yl}-benzofuran-2-carboxylic acid amide were obtained. 1H-NMR (500MHz, dbeta-DMSO) delta 12.18 (br s, 1H)1 8.49 (d, 1 H, J = 1.8 Hz), 8.33 (d, 1 H, J = 1.8 Hz), 7.99 (br. s, 1 H), 7.57 (br. s, 1 H), 7.47 (d, 1H1 J = 9.9 Hz), 7.40 (s, 1 H), 7.17 (m, 2H), 6.35 (s, 1 H), 3.33 (m, 4H), 3.11 (m, 4H)1 2.81 (m, 2H), 2.38 (m, 2H), 1.76 (m, 2H), 1.54 (m, 2H). P08033 HN.doc27HPLC-MS: Chromolite SpeedROD RP-18e 50-4, 6 mm solvent A: water + 0.1 % TFA solvent B: acetonitrile + 0.1% TFA 5 flow: 2.4 mL/min gradient: 0,0 min 4% B2.6 min 100% B Rt: 1.909 min[M+H]+: 398

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 1187322-51-5, 6-Amino-5-iodonicotinonitrile.

Reference:
Patent; MERCK PATENT GMBH,; WO2009/112139; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 582303-10-4, name is (2,6-Dimethylpyridin-3-yl)methanol. This compound has unique chemical properties. The synthetic route is as follows. SDS of cas: 582303-10-4

Step B: 3-(chloromemviy2,6-dimethylpyridine (3)The solution of compound (2,6-dimethylpyridin-3-yl)methanol (0.76 g, 5.6 mmol) in SOCl2(5 mL) was stirred at room temperature for 1 hour and then concentrated to give the crude product 3 which was used for next step directly without further purification. LCMS (ESI) m/z = 156.1 (M+H)+.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, 582303-10-4, (2,6-Dimethylpyridin-3-yl)methanol.

Reference:
Patent; MERCK SHARP & DOHME CORP.; KUDUK, Scott, D.; MCCOMAS, Casey, C.; REGER, Thoma, S.; QI, Changhe; WO2014/150114; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem