Day: March 16, 2022

Synthetic Route of 884495-01-6, Adding some certain compound to certain chemical reactions, such as: 884495-01-6, name is 4-Bromo-5-fluoro-2-hydroxypyridine,molecular formula is C5H3BrFNO, 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 884495-01-6.

A mixture of 4-bromo-5-fluoropyridin-2-ol (442 mg, 2.31 mmol), ethyl 2-iodo-4-methylpentanoate (937 mg, 3.47 mmol) and K2CO3 (958 mg, 6.94 mmol) in MeCN (10 mL) was stirred at 85 C. overnight and filtered. The filtrate was concentrated in vacuo, and the residue was purified by silica gel column (pet. ether_EtOAc=4:1) to give the desired product ethyl 2-(4-bromo-5-fluoro-2-oxopyridin-1(2H)-yl)-4-methylpentanoate as a colorless oil (402 mg). Yield 52% (97% purity, UV=214 nm, ESI 334.0 (M+H)+).

According to the analysis of related databases, 884495-01-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Morphic Therapeutic, Inc.; Bursavich, Matthew G.; Troast, Dawn M.; Harrison, Bryce A.; Lippa, Blaise S.; Rogers, Bruce N.; Konze, Kyle D.; Gerasyuto, Aleksey I.; Day, Tyler; Lin, Fu-Yang; Hahn, Kristopher N.; Svensson, Mats A.; Kim, Byungchan; Zhong, Cheng; Lugovskoy, Alexey A.; Sosa, Brian; (263 pag.)US2019/315692; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 865664-04-6, Adding some certain compound to certain chemical reactions, such as: 865664-04-6, name is 2-Chloro-3-cyclopropylpyridine,molecular formula is C8H8ClN, 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 865664-04-6.

Palladium(ll) acetate (61 mg, 0.27 mmol) and di-fert-butyl[3,4,5,6-tetramethyl-2′,4′,6′-tri(propan-2-yl)biphenyl-2-yl]phosphane (130 mg, 0.27 mmol) were added to a mixture of C6 (615 mg, 4.00 mmol), C5 (1 .0 g, 2.6 mmol) and cesium carbonate (2.6 g, 8.0 mmol) in 1,4-dioxane (25 mL). The reaction mixture was stirred at 120 C under microwave irradiation for 5 hours, then diluted with ethyl acetate (50 mL) and filtered. After removal of solvents in vacuo, the residue was purified via silica gel chromatography (Gradient: 0% to 25% ethyl acetate in petroleum ether) to provide the product as a yellow gum. Yield: 900 mg, 1 .8 mmol, 69%. LCMS m/z 494.1 [M+H]+. 1 H NMR (400 MHz, CDCl3) delta 8.02 (dd, J=4.8, 1.8 Hz, 1 H), 7.30 (dd, J=7.4, 1.8 Hz, 1 H), 7.11 -7.14 (m, 1 H), 7.08-7.10 (m, 2H), 7.01 (dd, J=7.5, 4.8 Hz, 1 H), 5.51 (AB quartet, JAB=9.3 Hz, DeltanuAlphaBeta=3.8 Hz, 2H), 3.74-3.80 (m, 2H), 3.08 (s, 3H), 2.18 (s, 3H), 2.16-2.24 (m, 1 H), 1.70 (s, 3H), 1.00-1.06 (m, 4H), 0.74-0.79 (m, 2H), 0.03 (s, 9H).

According to the analysis of related databases, 865664-04-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PFIZER INC.; BRODNEY, Michael Aaron; DAVOREN, Jennifer Elizabeth; DOUNAY, Amy Beth; EFREMOV, Ivan Viktorovich; GRAY, David Lawrence Firman; GREEN, Michael Eric; HENDERSON, Jaclyn Louise; LEE, Chewah; MENTE, Scot Richard; O’NEIL, Steven Victor; ROGERS, Bruce Nelsen; ZHANG, Lei; WO2014/207601; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1049744-89-9 ,Some common heterocyclic compound, 1049744-89-9, molecular formula is C6H7ClF3N3, 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 5-(4-methoxyphenyl)-1,2,4-oxadiazole-3-carbaldehyde (500 mg, 2.40 mmol) and2-hydrazino-5-(trifluoromethyl)pyridine hydrochloride(877 mg, 2.52 mmol) in MeCN (10 n) was stirred atRT for 3 h. The resulting suspension was diluted with water (10 mL) and filtered. The filter cake was washed with water (10 mL) and dried overnight invacuum oven (50 C, 20 mbar) to give the title compound as a brown solid (630 mg, 1.73 mmol, 72%,Ca. 90:10 mixture of stereoisomers).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1049744-89-9, its application will become more common.

Reference:
Patent; BAYER CROPSCIENCE AKTIENGESELLSCHAFT; KENNEDY, Jason W. J.; VON MORGENSTERN, Sascha; (37 pag.)WO2016/135062; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 853909-08-7, 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 853909-08-7, name is 5-Ethynyl-2-fluoropyridine. This compound has unique chemical properties. The synthetic route is as follows.

General procedure: Under argon, to a solution containing 3-aminoquinuclidine bishydrochloridesalt 2 (212 mg, 1.00 mmol) and 1H-imidazole-1-sulfonyle azide 1 (232 mg, 1.10 mmol) in MeOH (6 mL) wasportion wise added K2CO3 (415 mg, 3.00 mmol) and next a catalyticamount of CuSO4, 5H2O (25 mg, 0.10 mmol). The reaction mixturewas stirred at room temperature for 6 h and then concentratedunder reduced pressure. The crude solid was solubilized in Et2O(10 mL), filtered and the precipitate washed with an additionalamount of Et2O (10 mL). The combined organic layers were reducedunder reduced pressure and the (R) intermediate 3a used in thenext step. After addition of MeOH (6 mL), the desired terminalalkyne 4 (1.00 mmol) and next CuSO4, 5H2O (25 mg, 0.10 mmol),sodium ascorbate (40 mg, 0.20 mmol) were successively added. Thereaction mixturewas stirred for 12 h at room temperature. Volatileswere evaporated under reduced pressure and the residue purifiedby flash chromatography. When some traces of imidazole wereobserved, EtOAc (20 mL) was added. After washing with water(2 10 mL), the organic layer was dried over MgSO4, filtered andevaporated under reduced pressure to afford the pure derivative of type IIIa.

According to the analysis of related databases, 853909-08-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Ouach, Aziz; Pin, Frederic; Bertrand, Emilie; Vercouillie, Johnny; Gulhan, Zuhal; Mothes, Celine; Deloye, Jean-Bernard; Guilloteau, Denis; Suzenet, Franck; Chalon, Sylvie; Routier, Sylvain; European Journal of Medicinal Chemistry; vol. 107; (2016); p. 153 – 164;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 17570-98-8, 2-(Bromoacetyl)pyridine hydrobromide, 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, SDS of cas: 17570-98-8, blongs to pyridine-derivatives compound. SDS of cas: 17570-98-8

2-Bromo-1-(pyridin-2-yl)ethanone hydrobromide 8a(20.0 g, 71.1 mmol) and K2CO3 (14.8 g, 107 mmol) were suspended in acetone (100 mL), andthe suspension was stirred at room temperature for 1.5 hr. To a solution of ethyl cyanoacetate (60.4 g, 534 mmol) in acetone (100 mL) was addedK2CO3 powder (29.6 g, 214 mmol), and the mixture was stirred at 45C for 1 hr. To this mixture was added dropwise the suspension obtained earlier by small portions at 45C, and the resulting mixture was stirred at 45C for 3 h, filtered after cooled to room temperature, and then concentrated under reduced pressure. The residue was taken up withEtOAc, washed with H2O and brine, dried over anhydrous MgSO4, and concentrated under reduced pressure. To the obtained oil was added 4 mol/L HCl/EtOAc (250 mL) and the mixture was stirred at 60 C for 3 h, and concentrated under reduced pressure. A solution ofNaHCO3 was added to the residue and the mixture was extracted with EtOAc, washed with brine, dried over anhydrous MgSO4,and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane/EtOAc = 4/1), then added dropwise 4 mol/L HCl/EtOAc (20 mL) after dissolved in EtOAc (20 mL), concentrated under reduced pressure, and crystalized from EtOAc to yieldcompound 10a (3.08 g, 15%) as a colorless solid: 1H-NMR (DMSO-d6)d 1.30 (3H, t, J=7.0 Hz), 4.25 (2H, q, J=7.0 Hz), 7.48-7.54 (2H, m), 8.13-8.19 (2H, m), 8.61-8.63 (1H, m), 13.47 (1H, br), 1H not detected.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,17570-98-8, 2-(Bromoacetyl)pyridine hydrobromide, and friends who are interested can also refer to it.

Reference:
Article; Nishida, Haruyuki; Arikawa, Yasuyoshi; Hirase, Keizo; Imaeda, Toshihiro; Inatomi, Nobuhiro; Hori, Yasunobu; Matsukawa, Jun; Fujioka, Yasushi; Hamada, Teruki; Iida, Motoo; Nishitani, Mitsuyoshi; Imanishi, Akio; Fukui, Hideo; Itoh, Fumio; Kajino, Masahiro; Bioorganic and Medicinal Chemistry; vol. 25; 13; (2017); p. 3298 – 3314;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 902837-42-7, 7-Bromo-1H-pyrrolo[3,2-c]pyridine, 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: 902837-42-7, blongs to pyridine-derivatives compound. Recommanded Product: 902837-42-7

Production Example 46 To a mixture of 7-bromo-1H-pyrrolo[3,2-c]pyridine (0.16 g) and THF (6.0 mL) were added di-tert-butyl dicarbonate (0.26 g) and N,N-dimethyl-4-aminopyridine (0.010 g) at room temperature, followed by stirring at room temperature for 17 hours. The reaction mixture was concentrated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane=0 to 25%) to obtain tert-butyl 7-bromo-1H-pyrrolo[3,2-c]pyridine-1-carboxylate (0.22 g).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,902837-42-7, 7-Bromo-1H-pyrrolo[3,2-c]pyridine, and friends who are interested can also refer to it.

Reference:
Patent; Astellas Pharma Inc.; EP2277858; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 20511-12-0 , The common heterocyclic compound, 20511-12-0, name is 5-Iodopyridin-2-amine, molecular formula is C5H5IN2, 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.

Bromine (3ml) was added dropwise to a solution of 2-amino-5-iodo-pyridine (5g, 20mmol) in 48% hydrobromic acid in water (10ml). AIL ice bath was used to cool the system. Sodium nitrite (3.4 g in 5ml of water) was then added dropwise so that the temperature does not go above 15C. After the addition was complete, sodium hydroxide (16g) in water (40ml) was added. Brown solid precipitated and was extracted with DCM (50ml). The DCM extract was washed with water, brine, dried over MgS04 and evaporated in vacuo to give 2-bromo-5-iodo-pyridine (4.4g, 78%).

The synthetic route of 20511-12-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F2G LTD; WO2005/92304; (2005); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 228410-90-0 , The common heterocyclic compound, 228410-90-0, name is 5-bromo-2-hydroxy-3-nitro-4-picoline, molecular formula is C6H5BrN2O3, 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. 5-Bromo-1,4-dimethyl-3-nitropyridin-2(1H)-one A solution of 5-bromo-4-methyl-3-nitropyridin-2-ol (15.00 g, 64.37 mmol) [Combi-Blocks, AN-1086] in N,N-dimethylformamide (250 mL) was treated with sodium hydride (3.09 g, 77.3 mmol) (60% dispersion on mineral oil) slowly and portionwise, and stirred at RT for 30 min. The reaction mixture was treated with methyl iodide (4.81 mL, 77.2 mmol) dropwise and stirred at RT for 3 h. LCMS indicated a clean peak for methylated product. The reaction mixture was poured over water/ice (?400 mL) and allowed to stir while the ice melted. The aqueous mixture was extracted with EA. The organic layer was washed with water (3*) and brine, dried with magnesium sulfate, filtered, and concentrated to give the desired product (14.9 g, 93%) that was used without further purification. LCMS calculated for C7H8BrN2O3 (M+H)+: m/z=247.0, 249.0. found: 247.0, 248.9.

The synthetic route of 228410-90-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Incyte Corporation; Yue, Eddy W.; Combs, Andrew P.; Buesking, Andrew W.; US2015/148375; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1452-94-4, 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.1452-94-4, name is Ethyl 2-chloronicotinate, molecular formula is C8H8ClNO2, molecular weight is 185.61, as common compound, the synthetic route is as follows.

Example 1; Synthesis of cis-1-(2-fluoro-6-methylbenzoyl)-2-phenylpiperidine-3-carboxylic acid (3-trifluoromethylphenyl)amide; a) Pd(PPh3)4 (3.0 g, 2.6 mmol) was added to a solution of 2-chloro-3-carboxyethylpyridine (25 g, 134.7 mmol), phenylboronic acid (21.04 g, 172.6 mmol) and K2CO3 (55.1 g, 399 mmol) in 1,4-dioxane (200 mL) and water (200 mL). The reaction mixture was heated at 100 C. for 2 h. The solution was then cooled to room temperature and the dioxane was removed under reduced pressure. The resulting aqueous layer was extracted with ethyl acetate, and the combined organic layers were dried (Na2SO4), filtered through celite, and concentrated under reduced pressure. The residue was purified by flash chromatography (SiO2, 10-100% EtOAc/hexanes) to get the 2-phenylpyridine derivative in 91% yield (27.98 g). LC-MS Rt (retention time): 2.45 min, MS: (ES) m/z 228 (M+H+).

Statistics shows that 1452-94-4 is playing an increasingly important role. we look forward to future research findings about Ethyl 2-chloronicotinate.

Reference:
Patent; ChemoCentryx, Inc.; US2010/160320; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 149246-87-7, 5-(Pyridin-3-yl)-1H-pyrazol-3-amine, 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, Safety of 5-(Pyridin-3-yl)-1H-pyrazol-3-amine, blongs to pyridine-derivatives compound. Safety of 5-(Pyridin-3-yl)-1H-pyrazol-3-amine

General procedure: 1H-Pyrazol-5-amine 1 (1 equiv.), 3-oxopropanenitrile 2 (1 equiv.), benzaldehyde 3 (1 equiv.), and Et3N (2 equiv.) were stirred in DMF (1 M) at 90 °C for 16 h. The volatiles were removed under reduced pressure (or positive N2 (g) pressure). Sodium nitrite (3 equiv.) and acetic acid (134 equiv.) were added to the crude material, and the reaction mixture was stirred for 10 min. The volatiles were removed under reduced pressure (or positive N2 (g) pressure), and the crude reaction mixture was subjected to silica gel column chromatography with ethyl acetate in hexanes.

The synthetic route of 149246-87-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Hill, Matthew D.; Synthesis; vol. 48; 14; (2016); p. 2201 – 2204;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem