Tag: M.W:100-200

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. 69716-28-5, name is N-Hydroxypicolinimidoyl chloride, 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. Formula: C6H5ClN2O

1-B. Alternative Preparation of ethyl 3-(pyridin-2-yl)-4-(trifluoromethyl)isoxazole-5- carboxylate; [00112] To a solution of (Z)-ethyl 2-bromo-4,4,4-trifluorobut-2-enoate (1.58 g, 6.39 mmol) and (E,Z)-N-hydroxypicolinimidoyl chloride (2.0 g, 12.8 mmol) in ethyl acetate (10 mL) was added indium (III) chloride (0.283 g, 1.28 mmol). The resulting mixture was stirred for 30 minutes under nitrogen, and then potassium hydrogen carbonate (0.959 g, 9.58 mmol) was added. The reaction mixture was stirred for 14 h. The mixture was filtered, and the solid was rinsed with ethyl acetate (10 ml). The filtrate was washed with a saturated aqueous solution of ammonium chloride (10 mL), washed with brine (10 mL), and concentrated. The residue was purified by flash silica gel chromatography using EtOAc/Hexane as the solvent. The fractions containing the product were pooled and concentrated to give the product as an oil (1.15g, 63% yield) as a mixture of the desired isomer, ethyl 3-(pyridin-2-yl)-4- (trifluoromethyl)isoxazole-5-carboxylate and the undesired isomer, ethyl 3-(pyridine- 2-yl)-5-(trifluoromethyl)isoxazole-4-carboxylate in a ratio of approximately 30: 1. MS m/e 287.02 (M+H+); 1H NMR (DMSO, 400 MHz) delta 8.73 (d, J = 4.0 Hz, IH), 8.01(m, IH), 7.87(d, J = 8.0 Hz, IH), 7.65(m, IH), 4.53 (q, J = 8.0 Hz, 2H,), 1.46 (t, J = 8.0 Hz, 3H); HPLC (XBridge 5mu Cl 8 4.6×50 mm, 4 mL/min; Solvent A: 10 % MeOH/water with 0.2 % H3PO4; Solvent B: 90 % MeOH/water with 0.2 % H3PO4, gradient with 0-100 % B over 4 minutes): 3.57 minutes.

With the rapid development of chemical substances, we look forward to future research findings about 69716-28-5.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; PITTS, William, J.; DYCKMAN, Alaric, J.; SPERGEL, Steven, H.; WATTERSON, Scott, Hunter; WO2010/85582; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 13466-41-6 ,Some common heterocyclic compound, 13466-41-6, molecular formula is C6H7NO, 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.

Step 1 3-(4-Methyl-2-oxo-2H-pyridin-1-yl)-5-nitro-benzoic Acid Methyl Ester; To a 25 ml round-bottomed flask was added 2-Hydroxy-4-methylpyridine (17.9 mg, 0.164 mmol), 3-Iodo-5-nitro-benzoic acid methyl ester (40 mg, 0.137 mmol), CuI (5.2 mg, 0.027 mmol) and 1,4-dioxane (10 ml). The reaction mixture was stirred for 5 minutes to the dissolve 2-Hydroxy-4-methylpyridine and 3-iodo-5-nitro-benzoic acid methyl ester, after which 1,10-phenanthroline (9.84 mg, 0.055 mmol) was added, followed by K3PO4 (174 mg, 0.082 mmol). The reaction mixture was flushed with N2, and heated to 110 C. for 24 hours. After cooling to room temperature, the mixture was diluted with H2O, and extracted with ethyl acetate. The combined organic layer was washed with brine, dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by flash chromatography to give 3-(4-Methyl-2-oxo-2H-pyridin-1-yl)-5-nitro-benzoic acid methyl ester (39.45 mg, 61%) as light yellow solid. MS (M+H)=289.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,13466-41-6, its application will become more common.

Reference:
Patent; Roche Palo Alto LLC; US2009/163502; (2009); 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.36052-27-4, name is Methyl 3-aminopicolinate, molecular formula is C7H8N2O2, molecular weight is 152.15, as common compound, the synthetic route is as follows.Product Details of 36052-27-4

Step 2;. Preparation of 3-amino-6-bromo-pyridine-2-carboxylic acid methyl ester; Add a solution of 2 M sulfuric acid (2 mL) to a suspension of 3-amino-pyridine-2- carboxylic acid methyl ester (0.59 g, 3.88 mmol) in water (10 mL) and stir the mixture until the precipitate is dissolved. Add dropwise a solution of bromine (0.199 mL, 3.88 mmol) in acetic acid (1.5 mL). Add a solution of 2 M sodium hydroxide until pH = 6 and extract with ethyl acetate. Separate the organic layer and extract with ethyl acetate. Dry the combined organic layers over anhydrous sodium sulfate, filter, and remove the solvent under reduced pressure. Purify the residue using silica gel chromatography eluting with ethyl acetate/hexanes to afford the title compound (0.616 g, 69%). H-NMR (CDCl3,300 MHz) : No. 3.90 (s, 3 H) ; 6.90 (d, J = 8.5 Hz, 1H), 7.30 (d, J= 8.5 Hz, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,36052-27-4, Methyl 3-aminopicolinate, and friends who are interested can also refer to it.

Reference:
Patent; ELI LILLY AND COMPANY; WO2005/97805; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 146679-66-5, 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.146679-66-5, name is 3-Bromo-4-pyridinemethanol, molecular formula is C6H6BrNO, molecular weight is 188.02, as common compound, the synthetic route is as follows.

To a solution of 3bromo-4-(hydroxymethyl)pyridine 4 (1.593 g, 8.47 mmol) in dichioromethane (20 mL) was added imidazole (0.692 g, 10.17 mmol) and tert-butyldimethylsilyl chloride (1.534 g, 10.17 mmol) at 0C and the reaction mixture was stirred for 18 h at ft. The solution was extractedwith DCM and the organic phase was washed with brine, dried and concentrated under vacuum. Purification by silica gel column chromatography using EtOAc/DCM (1/9) as eluent gave j (2.518 g, 98 %).?H NMR (CDC13, 300 MHz, 298 K, 6 ppm): 8.60 (s, 1 H), 8.52 (d, IH, J 4.8 Hz), 7.52 (d, 1H, J= 4.8 Hz), 4.71 (s, 2 H), 0.97 (s, 9 H), 0.15 (s, 6H).13C NMR (CDC13, 75.5 MHz, 298K, 8 ppm): 150.90, 149.67, 148.54, 122.19, 119.20, 63.78, 25.96,18,43, 5.31.GC/MS (m/z): [M-t-Butyl] 244. IR (KBr, v, cm?): 3046, 2953, 2887, 2857, 2709, 1926, 1789, 1737, 1587, 1472, 1445, 1397, 1373, 1360, 1261, 1172, 1114, 1079, 839, 778, 706, 673.

The chemical industry reduces the impact on the environment during synthesis 146679-66-5, I believe this compound will play a more active role in future production and life.

Reference:
Patent; INSA (INSTITUT NATIONAL DES SCIENCES APPLIQUEES) DE ROUEN; CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE (CNRS); UNIVERSITE DE ROUEN; VFP THERAPIES; MARSAIS, Francis; LEVACHER, Vincent; PAPAMICAEL, Cyril; BOHN, Pierre; PEAUGER, Ludovic; GEMBUS, Vincent; LE FUR, Nicolas; DUMARTIN-LEPINE, Marie-Laurence; WO2014/114742; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 885266-91-1, 1-(2-Aminopyridin-4-yl)ethanol, 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, Recommanded Product: 885266-91-1, blongs to pyridine-derivatives compound. Recommanded Product: 885266-91-1

To a solution of 8-(tert-butylamino)-6-chloro-2-(2-hydroxyethyl)-2,7-naphthyridin- l(2H)-one (29.6 mg, 0.10 mmol) in 1,4-dioxane (1 mL) were added crude l-(2-aminopyridin-4-yl)ethanol (estimate 0.20 mmol), Cs2CO3 (130.3 mg, 0.40 mmol), and a catalytic amount of Pd(dba)3 and Xantphos. The reaction mixture was purged with N2 and heated at 100 C overnight. The mixture was then cooled, quenched with H2O and extracted with EtOAc. The combined organic layer was concentrated and purified by preparatory LC/MS to provide title compound; 1H NMR (CD3OD, 400 MHz) delta 8.16 (d, /= 5.6 Hz, 1H), 7.69 (s, 1H), 7.23 (d, / = 7.6 Hz, 1H), 6.97 (d, /= 5.6 Hz, 1H), 6.59 (s, 1H), 6.24 (d, / = 7.6 Hz, 1H), 4.81 (q, / = 6.4 Hz, 1H), 3.99 (t, /= 5.2 Hz, 2H), 3.81 (t, /= 5.2 Hz, 2H), 1.57 (s, 9H), 1.45 (d, / = 6.4 Hz, 3H); ESI-MS ml z 398.2 (MH+).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,885266-91-1, 1-(2-Aminopyridin-4-yl)ethanol, and friends who are interested can also refer to it.

Reference:
Patent; IRM LLC; CHE, Jianwei; CHEN, Bei; DING, Qiang; HAO, Xueshi; HE, Xiaohui; JIANG, Songchun; JIN, Qihui; JIN, Yunho; LIU, Hong; LIU, Yahua; OKRAM, Barun; UNO, Tetsuo; WU, Xu; YANG, Kunyong; ZHU, Xuefeng; WO2011/14515; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 68325-15-5 , The common heterocyclic compound, 68325-15-5, name is 3-Chloro-4-cyanopyridine, molecular formula is C6H3ClN2, 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.

Reference Production Example 80To a mixture of 1.39 g of 3-chloro-isonicotinonitrile, 1.10 g of 2,2,2- trifluoroethanol and 5 mL of DMF, 0.40 g of 60% sodium hydride (oily) was added under ice cooling, followed by stirring for 20 minutes, heating to room temperature and further stirring for 7.5 hours. After ice cooling again, 0.20 g of 60% sodium hydride (oily) was added, followed by heating to room temperature and further stirring for 15 hours. Under ice cooling, water was added and the precipitated crystal was washed with water, collected by filtration and then dried under reduced pressure to obtain 1.63 g of 3-(2,2,2-trifluoroethoxy)- isonicotinonitrile. H-NMR (CDC13 ) delta : 8.53-8.52(br m, 1H), 8.51(d, J=4.9Hz, 1H), 7.53(dd, J=4.9, 0.6Hz,1H), 4.62(q, J=7.7Hz, 2H)

The synthetic route of 68325-15-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SUMITOMO CHEMICAL COMPANY, LIMITED; OTSUKI, Junko; WO2011/49222; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 5912-18-5 , The common heterocyclic compound, 5912-18-5, name is 4,6-Dichloro-1H-pyrrolo[2,3-b]pyridine, molecular formula is C7H4Cl2N2, 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.

4,6-dichloro-1H-pyrrolo[2,3-b]pyridine (1.0 eq) was dissolved in DMF and the temperature was lowered to minus 10 C.To the mixture was added N-iodosuccinimide (1.1 equivalent), the temperature was raised to room temperature, and stirred for 1 hour. After the reaction, ice water was added to induce precipitation. The formed precipitate was filtered to give the desired compound as white. (Yield: 100%).

The synthetic route of 5912-18-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Dae Caliber Buk Peak Medical Industry Promotion Foundation; Korea Research Institute of Bioscience and Biotechnology; Daegu Gyeongbuk Institute of Science & Technology; Choi Hwan-geun; Go Eun-hwa; Cho Jung-hui; Son Jeong-beom; Go I-gyeong; Park Jin-hui; Kim So-yeong; Kang Seok-yong; Lee Seung-yeon; Ryu Hui-yun; Kim Nam-du; Kim Sang-beom; Lee Seon-hwa; Kim Da-ye; Lee Seon-ju; Cho Seong-chan; Lee Gyu-seon; Ryu Gwon; Choi Mi-ri; Gu Ja-uk; Huh Hyang-suk; (84 pag.)KR101896568; (2018); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 74115-13-2, 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.74115-13-2, name is 5-Bromo-3-pyridinol, molecular formula is C5H4BrNO, molecular weight is 174, as common compound, the synthetic route is as follows.

To a solution of 5-bromopyridin-3-ol (LI) (174 mg, 1.0 mmol) in DMF (3 mL) was added potassium carbonate (415 mg, 3.0 mmol). The slurry was heated at 90C for 1 hour and then cooled to 25C. The (bromomethyl)benzene (LV) (171 mg, 1.0 mmol) was added and the mixture was stirred at 25C overnight. The reaction was worked-up using a saturated sodium bicarbonate and ethyl acetate extraction. The product was purified by ISCO column eluted with 40- 100% EtOAc-Hexanes. The 3-(benzyloxy)-5-bromopyridine (LVI) (105 mg, 0.398 mmol, 39.8 % yield) was obtained as yellow oil.. MS: 266.1. ESIMS found for C12H10BrNO m/z 266.1 (M+H).

Statistics shows that 74115-13-2 is playing an increasingly important role. we look forward to future research findings about 5-Bromo-3-pyridinol.

Reference:
Patent; SAMUMED, LLC; KC, Sunil Kumar; WALLACE, David Mark; CAO, Jianguo; CHIRUTA, Chandramouli; HOOD, John; (322 pag.)WO2016/40193; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 70165-31-0, 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 70165-31-0 as follows.

A tetrahydrofuran solution of a boranetetrahydrofuran complex (1 M; 50 mL) was added to a solution of 6-cyanonicotinic acid (0.85 g) in tetrahydrofuran (20 mL) under ice-water cooling, followed by stirring at room temperature overnight. Methanol was added to the mixture under ice-water cooling, and then a 10% hydrogen chloride in methanol was added to the mixture, followed by stirring for 1 hour at 40C at room temperature. The solvent was removed under reduced pressure, and the resultant residue was purified by means of silica gel column chromatography [Chromatorex NH] (eluent; methanol : methylene chloride=1 : 1) to prepare the titled compound (1.54 g, Example Intermediate 36-1).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,70165-31-0, its application will become more common.

Reference:
Patent; MOCHIDA PHARMACEUTICAL CO., LTD.; EP1445250; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 40473-01-6, 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. 40473-01-6, name is 2-Bromo-5-chloropyridine. A new synthetic method of this compound is introduced below.

Intermediate 1 : methyl delta-chloro^-pyridinecarboxylate To a solution of 2-bromo-5-chloropyridine (30.0 g, 155.9 mmol) in MeOH (280 ml.) was added Pd(OAc)2 (3.5 g, 10.8 mmol), dppf (17.3 g, 37.96 mmol), Et3N (42.0 ml_, 312 mmol). The resulting mixture was stirred at 500C under a CO atmosphere (15 psi) for 24 h, then concentrated under reduced pressure to give crude residue. This residue was partitioned between EtOAc (3 X 500 ml.) and water (300 ml_). The combined organic layers were dried (Na2SO4) and evaporated. Flash chromatography of the residue over silica gel, by using 10:1 petroleum ether/EtOAc, afforded the title compound as a pale yellow solid (25 g, 93%): 1H NMR (400 MHz, CDCI3) delta ppm 8.60 (d, J = 1.60 Hz, 1 H), 8.01 (d, J = 8.40 Hz, 1 H), 7.75 (dd, J = 8.40, 2.40 Hz, 1 H), 3.92 (s, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,40473-01-6, its application will become more common.

Reference:
Patent; GLAXOSMITHKLINE LLC; CHRISTENSEN, Siegfried, Benjamin, IV; QIN, Donghui; CHEN, Shenglin; HUANG, Xing; LI, Di; LI, Fei; LI, Lei; LIN, Xiaojuan; LU, Shi; LU, Zhen; LV, Maoyun; WANG, Chuanning; WU, Chengde; XIAO, Mei; YU, Haiyu; ZHANG, Weina; ZHANG, Zhiliu; WO2010/141539; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem