Tag: M.W:200-300

Synthetic Route of 82205-58-1, 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. 82205-58-1, name is 1-(5-Nitropyridin-2-yl)piperazine. A new synthetic method of this compound is introduced below.

Step 3: 4-(5-Nitropyridin-2-yl)-N-(2-fluorophenyl)piperazine-l-carboxamide (B-4)To compound B-3 (6.6 g, 32 mmol) dissolved in dry THF (200 mL) was added triethylamine (8.8 mL, 63 mmol) and 2-fluorophenyl isocyanate (4.3 mL, 38 mmol). The resulting reaction mixture was heated at 80 C for 16 h then cooled to RT and concentrated. Water (150 mL) was added, and the aqueous solution was extracted with CH2CI2. The combined organic extract was dried (MgS04), filtered, and concentrated to give a yellow solid. The solid was triturated with water, filtered, and dried to give the product 4-(5-nitropyridin-2-yl)-N-(2- fluorophenyl)piperazine-l-carboxamide (B-4) as a yellow solid (11.4 g, 100% yield). MS (M+1): 346.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,82205-58-1, its application will become more common.

Reference:
Patent; SCHERING CORPORATION; TING, Pauline, C.; LEE, Joe, F.; ASLANIAN, Robert, G.; WO2011/31628; (2011); A1;,
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 872365-91-8, name is 2-Bromo-6-(difluoromethyl)pyridine. This compound has unique chemical properties. The synthetic route is as follows. Formula: C6H4BrF2N

To a stirred solution of 2-bromo-4-fluoropyridine (0.3 g, 1.71 mmol) in 1,4-dioxane (5 mL) was added hexamethylditin (0.43 mL, 2. immol). The reaction mixture was purged with N2 for 10 mm. and to it was added Pd(Ph3P)4 (0.20 g, 0.17 mmol). The reaction mixture was purged once again with N2 for another 10 mm and heated at 110 C for 2 h. Then, after cooling to room temperature, compound 1A (0.43 g, 1.7lmmol) was added and the mixture was purged with N2 for 5 mm., followed by the addition of Pd(Ph3P)4 (0.2 g, 0.17 mmol). The reaction was again heated at 110 C for 18 h. The reaction mixture was concentrated under vacuum to give a crude residue, which was purified by preparative HPLC (Condition N) to provide 6-(4?-fluoro- [2,2?-bipyridinj -3-yl)imidazo [1,2-al pyridine-3 -carbonitrile 16 (0.38 mg, 0.89 mmol, 52.3 % yield). LC-MS: m/z = 317.1 [M+Hf?; ret.time 1.41 mm; condition C. ?H NMR (400 MHz, DMSO-d6) 3 ppm 8.93 – 8.89 (m, 1H), 8.60 – 8.57 (m, 1H), 8.27 – 8.19 (m, 3H), 8.03 – 7.97 (m, 1H), 7.77 – 7.72 (m, 1H), 7.42 – 7.37 (m, 1H), 7.34 – 7.27 (m, 1H). Compound 49 was synthesized by reacting 4 (reference: WO 2015157093 Al and WO 2014055955 Al) and 2-bromo-6-(difluoromethyl)pyridine employing the experimental procedure described in Scheme 4 (Method-D). The crude residue was purified by preparative HPLC (condition-H) to yield 6-(6?-(difluoromethyl)- [2,2?-bipyridinj -3 -yl)imidazo[ 1,2- bjpyridazine-3-carbonitrile 49 (242 mg, 0.0604 mmol, 62.9 % yield). LCMS: m/z = 349.1 [M+Hf?; ret. time 1.53 mm. condition C. ?H NMR (400 MHz, DMSO-d6) oe ppm ppm 8.92 (dd, J4.6, 1.7 Hz, 1H), 8.36 (dd, J8.l, 1.0 Hz, 1H), 8.25 (d, J=9.3 Hz, 1H), 8.21 – 8.18 (m, 2H), 8.16 (t, J=7.8 Hz, 1H), 7.74 (dd, J=7.7, 4.8 Hz, 1H), 7.61 (d, J7.8 Hz, 1H), 7.43 (d, J9.5 Hz, 1H), 6.26 (s, 1H).

With the rapid development of chemical substances, we look forward to future research findings about 872365-91-8.

Reference:
Patent; RIGEL PHARMACEUTICALS, INC.; BRISTOL-MYERS SQUIBB COMPANY; DING, Pingyu; GELMAN, Marina; KINSELLA, Todd; SINGH, Rajinder; BHAMIDIPATI, Somasekhar; VELAPARTHI, Upender; BORZILLERI, Robert, M.; RAHAMAN, Hasibur; WARRIER, Jayakumar, Sankara; (232 pag.)WO2016/133838; (2016); 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. 891785-18-5, name is 3-(Benzyloxy)-5-bromo-2-chloropyridine, molecular formula is C12H9BrClNO, 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. Computed Properties of C12H9BrClNO

To a suspension of 68 3-(benzyloxy)-5-bromo-2-chloropyridine (25.7 mg, 86.0 mmol) and 41 potassium phosphate (54.9 g, 259 mmol) in 9 tetrahydrofuran (180 mL) were added successively 14 water (130 mL), 17 (E)-2-(3-methoxyprop-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (20.1 mL, 95.0 mmol) and [1,1?-bis(diphenylphosphino)-ferrocene]palladium(II) dichloride dichloromethane adduct (3.54 g, 4.33 mmol), and the mixture was stirred at room temperature for 2 hr. [1,1?-Bis(diphenylphosphino)-ferrocene]palladium(II) dichloride dichloromethane adduct (1.70 g, 2.04 mmol) was added again thereto, and the mixture was stirred at room temperature for 3 hr, warmed to 33 C., and stirred for 1 hr. The reaction solution was diluted with ethyl acetate (180 mL), and the insoluble substance was removed by filtration. The organic layer of the filtrate was washed with water and saturated brine, silica gel (50 g) was added thereto, and the mixture was stirred at room temperature for 1 hr. The silica gel was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel chromatography (hexane:ethyl acetate=15:1 to 4:3) to give 70 (E)-3-(benzyloxy)-2-chloro-5-(3-methoxyprop-1-en-1-yl)pyridine (20.9 g, yield 83%). 1H-NMR (DMSO-D6) delta: 3.29 (3H, s), 4.06-4.07 (2H, m), 5.29 (2H, s), 6.59-6.60 (2H, m), 7.32-7.49 (5H, m), 7.81 (1H, d, J=1.8 Hz), 8.02 (1H, d, J=2.1 Hz).

With the rapid development of chemical substances, we look forward to future research findings about 891785-18-5.

Reference:
Patent; JAPAN TOBACCO INC.; NAGAMORI, Hironobu; NISHIMARU, Tatsuya; TAKAGI, Masaki; MITANI, Ikuo; NAKAGAWA, Yuichi; US2019/152926; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 13959-02-9, name is 3-Bromoisonicotinic acid, the common compound, a new synthetic route is introduced below. HPLC of Formula: C6H4BrNO2

A mixture of 3.98 g of the acid obtained in the previous step (20 mmol, 1 eq.) in 50 ml of methanol is reflux heated in the presence of 4 ml of concentrated sulfuric acid. The mixture is allowed to return to ambient temperature and extracted 3 times with ethyl acetate. The organic phase is dried on Na2SO4 and the solvent is evaporated. 2.65 g (62%) of esterified product is obtained. NMR (1H, CDCl3): 4.02 (s; 3H), 7.64 (d, J=4.9 Hz; 1H), 8.63 (d, J=4.9 Hz; 1H), 8.88 (s; 1H).

The synthetic route of 13959-02-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Imbert, Thierry; Monse, Barbara; Koek, Wouter; US2005/80085; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 137628-17-2, 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. 137628-17-2, name is 2,3-Dibromo-5-chloropyridine, molecular formula is C5H2Br2ClN, 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 solution of compound 47.1 (10.0 g, 37.19 mmol) in THF (100 ml) was added slowly asolution of isopropylmagnesium chloride/lithium chloride (1.3 M in THF, 31 ml, 40.3 mmol)at -40 C. The solution was stirred for 30 mm at -40 C and DMF (8.5 ml, ill mmol) wasadded. The resulting solution was warmed to room temperature and stirred for 30 mm. Thereaction was quenched with 1M HCI (70 ml) and diethyl ether (60 ml) was added. The organic layer was separated and washed with 5% aqueous NaHCO3. The solvent was removed under vacuum. The resulting solids were dissolved in methanol (90 ml). Thesolution was cooled to 0 C NaBH4 (3.60 g, 95.2 mmol) was slowly added. The reaction mixture was stirred for 30 mm, then quenched with water (30 ml). The resulting mixture was concentrated under vacuum to approximately 40 ml. The resulting suspension was stirred vigorously at room temperature for 1 h and the solids were collected by filtration and driedin a vacuum to give compound 47.2 (7.20 g, 88%) as a colourless solid. 1H NMR (ODd3,400 MHz) O 2.33 (t, 1H), 4.73 (d, 2H), 7.88 (d, 1H), 8.26 (d, 1H). LCMS (221.9 [M+H]).

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 137628-17-2, 2,3-Dibromo-5-chloropyridine.

Reference:
Patent; THE UNIVERSITY OF SHEFFIELD; RICHARDS, Gareth; SKERRY, Timothy, M.; HARRITY, Joseph, P.A.; ZIRIMWABAGABO, Jean-Olivier; TOZER, Matthew, J.; GIBSON, Karl, Richard; PORTER, Roderick, Alan; BLANEY, Paul, Matthew; GLOSSOP, Paul, Alan; (369 pag.)WO2018/211275; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 189278-27-1, 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 189278-27-1, name is 2-Bromo-6-(trifluoromethyl)pyridine. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 2-bromo-6-(trifluoromethyl)pyridine (200 mg, 0.885 mmol) in a solvent mixture of toluene (1.5 ml)/water (1.5 ml)/ethanol (0.7 ml) was added 3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)pyridine (200 mg, 0.738 mmol), cesium carbonate (601 mg, 1.844 mmol) and 1,1′-bis(diphenylphosphino)ferrocenepalladium(II) dichloride (30.3 mg, 0.037 mmol). The reaction mixture was heated in a benchtop microwave at 120 C. for 30 min. The reaction mixture was diluted with water and extracted with EtOAc. The organics were dried with MgSO4, filtered and then concentrated in vacuo. The residue was purified by column chromatography, eluting with 0-50% acetone in hexanes to afford 2-(1-(pyridin-3-yl)-1H-pyrazol-4-yl)-6-(trifluoromethyl)pyridine as a white solid (82 mg, 38.3%): mp 130-131 C.; 1H NMR (400 MHz, acetone-d6) delta 9.24 (d, J=2.4 Hz, 1H), 9.13 (d, J=0.5 Hz, 1H), 8.60 (dd, J=4.7, 1.4 Hz, 1H), 8.44 (s, 1H), 8.35 (ddd, J=8.3, 2.7, 1.5 Hz, 1H), 8.12 (qd, J=8.3, 4.7 Hz, 2H), 7.72 (dd, J=7.1, 1.5 Hz, 1H), 7.59 (ddd, J=8.3, 4.7, 0.7 Hz, 1H); EIMS m/z 290.

According to the analysis of related databases, 189278-27-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; DOW AGROSCIENCES LLC; Lowe, Christian T.; Trullinger, Tony K.; Hunter, Ricky; US2012/220453; (2012); 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. 65-22-5, name is 3-Hydroxy-5-(hydroxymethyl)-2-methylisonicotinaldehyde hydrochloride, molecular formula is C8H10ClNO3, 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-Hydroxy-5-(hydroxymethyl)-2-methylisonicotinaldehyde hydrochloride

H2L2 was prepared by stirring 2-aminophenol (0.218 g, 2.00 mmol) dissolved in 6 mL of methanol/KOH pH ca. 9.0 and pyridoxal hydrochloride (0.407 g, 2.00 mmol) in 8 mL methanol, at room temperature for 3 h. After cooling the mixture was kept at 4 C overnight and the orange solid was filtered, washed with water, cold methanol and diethyl ether and dried under vacuum. Yield: 85%, 0.390 g. MM (C14H14N2O3) = 258.3 g/mol. Elemental Analysis: Calc. forC14H14N2O3: C, 65.11; H, 5.46; N, 10.85; Found: C, 64.9; H, 5.7; N,10.7. ESI-MS: m/z [Found (Calcd)]: 259.15 (259.3) (100%) [L+H]+;257.11 (257.29) (100%) [L-H]-. UV-Vis in dmso, lambdamax/nm (epsilon/M-1cm-1): 295 (8282), 360 (11601), 463 (421); 1H NMR (dmso-d6, delta/ppm): 2.55 (s, 3H, H17); 4.89 (s, 2H, H18); 6.97 (t, 1H, H2); 7.07 (d, 1H,H6); 7.28 (t, 1H, H1); 7.69 (d, 1H, H3); 7.98 (s, 1H, H12); 9.30 (s, 1H,H9); 5.63 (s, 1H, R-OH) and 10.45 (s, 1H, Ar-OH). 13C NMR (dmso-d6,delta/ppm): 16.15 (C17); 57.83 (C18); 116.82 (C6); 119.64 (C2); 119.73(C3); 121.82 (C11); 129.43 (C12); 130.45 (C1); 131.30 (C4); 136.82(C10); 147.13 (C14); 151.98 (C15); 156.28 (C9) and 157.82 (C5).LogP = 2.21 [24].

With the rapid development of chemical substances, we look forward to future research findings about 65-22-5.

Reference:
Article; Cavaco, Isabel; Correia, Isabel; Costa Pessoa, Joao; Marques, Fernanda; Nunes, Patrique; Inorganica Chimica Acta; vol. 507; (2020);,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1211580-54-9, 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. 1211580-54-9, name is 4-Bromo-2-(difluoromethyl)pyridine. A new synthetic method of this compound is introduced below.

[0208] Step 2: (R)-benzyl 7-(3-(2-(difluoromethyl)pyridin-4-yl)-l-trityl- lH-indazol-5-yl)-6-oxo-2,7-diazaspiro[4.4]nonane-2-carboxylate : To a stirred solution of 4-bromo-2-(difluoromethyl)pyridine (0.520 g, 2.51 mmol) and bis(pinacolato)diboron (1.270 g, 5.02 mmol) in 1,4-dioxane (15 mL), was added potassium acetate (0.740 g, 7.53 mmol). The solution was degassed for 15 mins. [Iota, – bis(diphenylphosphino)ferrocene]dichloropalladium (II) DCM complex (0.102 g, 0.125 mmol) was added. The mixture was degassed for 10 mins followed by refluxing for 3 h. The mixture was cooled to rt and (i?)-benzyl 7-(3-iodo-l -trityl-lH-indazol-5-yl)-6-oxo- 2,7-diazaspiro[4.4]nonane-2-carboxylate (Intermediate 7) (1.523 g, 2.009 mmol) in ethanol: toluene: water (1 : 1 : 1, 15 mL) was added followed by potassium carbonate (1.733 g, 12.56 mmol). The solution was degassed for 20 mins. Tetrakis(triphenylphosphine)palladium(0) (0.145 g, 0.125 mmol) was added. The mixture was degassed for 10 mins followed by refluxing for 3 h. The mixture was cooled to rt and filtered through a Celite pad. To the filtrate was added cold water, and the mixture was extracted with ethyl acetate (3 X 50 mL). The combined organic layers were washed with water (30 mL) and brine (20 mL), dried over sodium sulfate, filtered and concentrated. The crude compound was purified by column chromatography (100-200 silica) using 50% ethyl acetate in hexane as eluent to afford (i?)-benzyl 7-(3-(2- (difluoromethyl)pyridin-4-yl)-l -trityl-lH-indazol-5-yl)-6-oxo-2,7-diazaspiro[4.4]nonane- 2-carboxylate (0.500 g, 0.658 mmol, 33% yield ) as an off white solid . XH NMR (400 MHz, DMSO-de) delta 8.81 (d, J= 5.1Hz, 1H), 8.37 (d, J = 1.5 Hz, 1H), 8.09-8.00 (m, 2H), 7.50 (br d, J = 9.5 Hz, 1H), 7.43-7.27 (m, 14H), 7.20 (dd, J = 1.8, 7.7 Hz, 7H), 6.49 (d, J = 9.2 Hz, 1H), 5.08 (d, J = 3.3 Hz, 2H), 3.91 (br t, J = 6.4 Hz, 2H), 3.66-3.36 (m, 4H), 2.22-2.03 (m, 3H), 1.97 (br d, J = 4.8 Hz, 1H). LCMS : 260.44 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1211580-54-9, 4-Bromo-2-(difluoromethyl)pyridine, and friends who are interested can also refer to it.

Reference:
Patent; KALYRA PHARMACEUTICALS, INC.; HUANG, Peter Qinhua; KAHRAMAN, Mehmet; SLEE, Deborah, Helen; BUNKER, Kevin, Duane; HOPKINS, Chad, Daniel; PINCHMAN, Joseph, Robert; ABRAHAM, Sunny; SIT, Rakesh, Kumar; SEVERANCE, Daniel, Lee; (248 pag.)WO2016/161160; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1186647-69-7, 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.1186647-69-7, name is 4-Chloro-3-iodo-1H-pyrazolo[4,3-c]pyridine, molecular formula is C6H3ClIN3, molecular weight is 279.47, as common compound, the synthetic route is as follows.

To a solution of 4-chloro-3-iodo-1H-pyrazolo[4,3-c]pyridine (2.00 g, 7.17 mmol) in DMF (30 mL) was added KOH (0.800 g, 14.3 mmol) and 1-(chloromethyl)-4-methoxybenzene (2.24 g, 14.3 mmol). The mixture was stirred at room temperature overnight. After concentration, the residue was purified by silica gel column chromatography eluting with petroleum ether/ethyl acetate (10:1 to 8:1) to give the title compound as a white solid (2.4 g, 82%).

The chemical industry reduces the impact on the environment during synthesis 1186647-69-7, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Genentech, Inc.; Chan, Bryan; Estrada, Anthony; Shore, Daniel; Sweeney, Zachary; US2014/288043; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 63897-12-1, 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 63897-12-1, name is 2,4-Dichloro-6-methyl-3-nitropyridine. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 2-aminopyrazine (0.900 g, 9.47 mmol) in DMSO (40 mL) was added potassium tert-butoxide (2.13 g, 18.9 mmol) followed by 2,4-dichloro-6-methyl-3-nitropyridine (2.00 g, 9.47 mmol). After stirring for 30 min at rt, sat. NH4Cl solution was added. The organic layer was separated and the water layer was extracted with CH2Cl2 three times. The combined organic layers were dried over anhydrous Na2SO4, filtered and concentrated. Chromatography on silica gel (0-70% ethyl acetatehexanes) provided the desired product (567 mg, 23%). MS (ESI) mass calcd. C10H8ClN5O2, 265.04. m/z found, 266.0 [M+H]+. 1H NMR (500 MHz, CDCl3) delta 8.69-8.62 (br s, 1H), 8.38-8.34 (m, 2H), 8.34-8.29 (m, 2H), 2.59-2.56 (m, 3H).

According to the analysis of related databases, 63897-12-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Janssen Pharmaceutica NV; Alcazar Vaca, Manuel Jesus; Andres Gil, Jose Ignacio; Chrovian, Christa C.; Coate, Heather R.; De Angelis, Meri; Dvorak, Curt A.; Gelin, Christine F.; Letavic, Michael A.; Savall, Brad M.; Soyode-Johnson, Akinola; Stenne, Brice M.; Swanson, Devin M.; US2014/275015; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem