Tag: M.W:200-300

Adding a certain compound to certain chemical reactions, such as: 1214336-41-0, Methyl 5-bromo-3-chloropicolinate, 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, name: Methyl 5-bromo-3-chloropicolinate, blongs to pyridine-derivatives compound. name: Methyl 5-bromo-3-chloropicolinate

[013381 NaBH4 (6 g, 158.52 mmol, 3.97 equiv) was added to a solution of methyl 5-bromo-3- chloropyridine-2-carboxylate (10 g, 39.92 mmol, 1.00 equiv) in methanol (150 mL) at 0C. The reaction was stirred for 3 h at 0C. The reaction was then quenched by water, diluted with ethyl acetate, washed with saturated sodium bicarbonate and brine, dried over anhydrous sodium sulfate, and concentrated under vacuum. This resulted in the title compound (8.9 g, crude) as a light yellow solid. LCMS [M+H] 224.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1214336-41-0, Methyl 5-bromo-3-chloropicolinate, and friends who are interested can also refer to it.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; ESTRADA, Anthony; VOLGRAF, Matthew; CHEN, Huifen; KOLESNIKOV, Aleksandr; VILLEMURE, Elisia; VERMA, Vishal; WANG, Lan; SHORE, Daniel; DO, Steven; YUEN, Po-wai; HU, Baihua; WU, Guosheng; LIN, Xingyu; LU, Aijun; (537 pag.)WO2016/128529; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 166266-19-9 ,Some common heterocyclic compound, 166266-19-9, molecular formula is C6H7IN2, 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.

In a 50 mL resealable tube, a solution of 4-bromothiophenol (3.2 g, 17 mmol, Sigma- Aldrich, India) and 5-iodo-3-methyl-2-pyridinamine (2 g , 8.5 mmol) in DMSO (20 mL) was degassed by purging with argon gas at room temperature for 10 min. Potassium carbonate (3.53 g, 25.6 mmol) and cooper iodide (0.2 g ,1.1 mmol) were added sequentially to the above reaction mixture at room temperature under argon atmosphere The reaction tube was sealed under argon atmosphere and reaction mixture was heated at 150 C for 18 h. The reaction mixture was cooled to room temperature and filtered through a Celite (diatomaceous earth) pad. The filtrate was diluted with cold water (200 mL) and ethyl acetate (100 mL). The EtOAc layer was separated, washed with water, brine, dried over anhydrous Na2S04 and concentrated under reduced pressure. The residue obtained was purified by silica gel (60 to 120 mesh) column chromatography (eluent, 20% EtOAc-hexanes) to give 5-((4- bromophenyl)sulfanyl)-3-methyl-2-pyridinamine (2.7 g) as a white solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,166266-19-9, its application will become more common.

Reference:
Patent; AMGEN INC.; ASHTON, Kate; BOURBEAU, Matthew, Paul; HONG, Fang-Tsao; LIU, Longbin; NISHIMURA, Nobuko; NORMAN, Mark, H.; POON, Steve, F.; STEC, Markian, M.; ST. JEAN, David, J., JR; TAMAYO, Nuria, A.; YANG, Kevin, C.; WO2013/123444; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 7169-95-1, Adding some certain compound to certain chemical reactions, such as: 7169-95-1, name is 6-Bromo-2-methyl-[1,2,4]triazolo[1,5-a]pyridine,molecular formula is C7H6BrN3, 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 7169-95-1.

To a suspension of 6-bromo-2-methyl-[l,2,4]triazolo[1,5-a]pyridine (0.84 g, 4.00 mmol) in anhydrous l,4-dioxane (20 mL) were added Pd2(dba)3 (0.36 g, 0.40 mmol), BINAP (0.49 g, 0.79 mmol), diphenylmethanimine (1.45 g, 8.02 mmol) and t-BuONa (0.77 g, 8.01 mmol). The mixture was degassed and refilled with N2 for several times and heated to 105 C and stirred overnight. The mixture was concentrated in vacuo and the residue was purified by silica chromatography (EtOAc/PE (v/v) = 1/2 to 1/1 to EtOAc 100%) to afford the title compound as brown liquid (0.34 g, yield 27%).MS (ESI, pos. ion) m/z: 313.0 [M+H]+;1H NMR (400 MHz, CDCl3) d (ppm): 7.97-7.92 (m, 1H), 7.76 (d, J = 7.5 Hz, 2H), 7.51 (t, J = 7.3 Hz, 1H), 7.47-7.37 (m, 3H), 7.36-7.28 (m, 3H), 7.14 (dd, J= 7.4, 1.7 Hz, 2H), 6.99 (dd, J = 9.3, 1.8 Hz, 1H), 2.53 (s, 3H).

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. 7169-95-1, 6-Bromo-2-methyl-[1,2,4]triazolo[1,5-a]pyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; CALITOR SCIENCES, LLC; XI, Ning; LI, Minxiong; PENG, Ju; LI, Xiaobo; ZHANG, Tao; HU, Haiyang; CHEN, Wuhong; BAI, Changlin; KE, Donghua; CHEN, Peng; (281 pag.)WO2019/99311; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 78686-77-8, 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 78686-77-8 as follows.

Example 38 – Preparation of Intermediate 13 [ 00277 ] The synthesis of Intermediate 13 followed General Procedure 11 following: General Procedure 11 Intermediate 12 Intermediate 13 [ 00278 ] To a cold (0C) solution of 3-(5-amino-lH-pyrazol-3-yl) pyridine- 2(lH)-one (Intermediate 11, 9.0 g, 0.036 mol, 1 eq) in methanol (25 mL) was added sodium methoxide (25% in methanol, 15.5 mL, 0.072 mol, 2 eq). The reaction was stirred for 2 hours at room temperature. After completion of reaction, the reaction mixture was evaporated under reduced pressure, and the residue was poured into ice cold water under stirring. This mixture was extracted with ethyl acetate. The organic layer was dried over sodium sulpfate and concentrated under reduced pressure. The residue was purified by column chromatography using neutral silica gel, eluting with 25-30% ethyl acetate in hexane to give pure desired product (7.5 g, yield-84.74%>) m/z[M+H]+ 246.17 1H NMR (DMSO-d6, 400 MHz) delta 8.73 (d, J = 1.5 Hz, 1H), 8.41 (d, J= 1.5 Hz, 1H), 4.02 (d, J= 1.1 Hz, 3H), 3.86 (d, J= 1.1 Hz, 3H) ppm.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,78686-77-8, its application will become more common.

Reference:
Patent; VERSEON CORPORATION; SHORT, Kevin Michael; KITA, David Ben; ESTIARTE-MARTINEZ, Maria de los Angeles; PHAM, Son Minh; (244 pag.)WO2016/44662; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1159812-31-3, 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 1159812-31-3, name is 7-Bromo-2-methyl-[1,2,4]triazolo[1,5-a]pyridine. This compound has unique chemical properties. The synthetic route is as follows.

To boronic acid ester compound having triazole side chain (23, 2.63 g) and 7-bromotriazolopyridine derivative (24, 2.15 g, prepared as described in Example 4 using compound 18 of Example 5) in dioxane (50 mL) and water (12 mL), Na2CO3 (2.47 g) and Pd(Ph3P)4 (821 mg) were added and the reaction mixture was heated at 90 C. to 100 C. for 1.5 hours. The solvent was then removed under reduced pressure to reduce the volume by half, and water was added. After the resulting precipitate was filtered and dissolved in ethanol, 1.95 g of colorless compound 25 was precipitated (73%).Compound 25: 1H-NMR (300 MHz, DMSO-d6) 2.48 (br s, 3H), 3.96 (dd, 9.5, 6, 1H), 4.30 (dd, 9.5, 9.5, 1H), 4.86 (d, 5, 2H), 5.19 (ddt, 9.5, 6, 5, 1H), 7.30 (ddd, 7, 1.5, 1.5, 1H), 7.42 (dd, 8.5, 2, 1H), 7.58 (dd, 14, 2, 1H), 7.74 (dd, 8.5, 8.5, 1H), 7.77 (d, 1, 1H), 7.86 (br s, 1H), 8.18 (d, 1, 1H), 8.88 (d, 7, 1H);LRMS m/z 393 (M+, 7), 349 (14), 320 (6), 279 (8), 242 (10), 158 (11), 108 (21), 80 (29), 53 (100).

According to the analysis of related databases, 1159812-31-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Katoh, Issei; Aoki, Toshiaki; Suzuki, Hideyuki; Utsunomiya, Iwao; Kuroda, Norikazu; Iwaki, Tsutomu; US2011/98471; (2011); 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. 85686-48-2, name is 6-(2,4-Dichlorophenoxy)pyridin-3-amine, the common compound, a new synthetic route is introduced below. category: pyridine-derivatives

EXAMPLE 15 N-[6-(2,4-Dichlorophenoxy)pyridin-3-yl]-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxamide Following the procedure of Example 1, using 2,3,4,5-tetrahydro-1H-benzazepine and 6-(2,4-dichlorophenoxy)pyridin-3-amine as the starting materials, the title compound was prepared as a colorless solid (88%): mp 154-155 C.; IR (KBr) 3377, 3070, 3024, 3000, 2943, 2928, 2899, 1642, 1604, 1593, 1530, 1485, 1467, 1276, 1263, 1232, 1215, 863, 844, 819, 750, 734 cm-1; 1H NMR (400 MHz, CDCl3) delta7.98 (dd, J=8.8, 2.7 Hz, 1H), 7.93 (d, J=2.7 Hz, 1H), 7.45 (d, J=2.4 Hz, 1H), 7.26-7.23 (m, 1H), 7.18-7.12 (m, 4H), 7.10 (d, J=8.6 Hz, 1H), 6.95 (d, J=8.8 Hz, 1H), 6.50 (s, 1H), 3.68-3.66 (m, 4H), 3.02-3.00 (m, 4H); 13C NMR (100 MHz, CDCl3) delta158.8, 154.9, 149.0, 140.1, 139.0, 133.7, 131.9, 130.5, 130.3, 130.0, 128.0, 126.8, 124.3, 111.1, 47.1, 37.5; MS (EI) m/z 428 (M+-H), 426 (M+-H); HRMS (FAB) calcd. for C22H19Cl2N3O2+H: 428.0932, found: 428.0916; Anal. Calcd. for C22H19Cl2N3O2: C, 61.69; H, 4.47; N, 9.81. Found: C, 61.73; H, 4.54; N, 9.75.

The synthetic route of 85686-48-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Fu, Jian-Min; US2003/149024; (2003); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 946002-90-0, 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. 946002-90-0, name is (S)-1-(5-Bromopyridin-2-yl)pyrrolidin-3-ol. A new synthetic method of this compound is introduced below.

(S)-5-Bromo-2-(3-tert-butyl-dimethyl-silanyloxy)-pyrrolidin-l-yl)pyridine (G2). To a sol. of compound Gl (20.9 g, 85.8 mmol) in DMF (350 mL) at 0 0C were added imidazole (14.6 g, 215 mmol) and TBDMS-Cl (19.4 g, 129 mmol). This mixture was stirred at rt for 1.5 h, and aq. 10% K2CO3 (150 mL) was added. The mixture was extracted with heptane (2x). The combined org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (heptane/EtOAc 5 : 1 ? 4: 1 ? 3 : 1 ? 1 : 1) yielded the title compound (30.5 g, 99%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,946002-90-0, its application will become more common.

Reference:
Patent; ACTELION PHARMACEUTICALS LTD; WO2007/88514; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 76102-92-6, 2-Amino-N-(pyridin-3-yl)benzamide, 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, Computed Properties of C12H11N3O, blongs to pyridine-derivatives compound. Computed Properties of C12H11N3O

Example 30 To a solution of 180 mg of 2-[methyl(tetrahydro-2H-pyran-4-ylmethyl)amino]-1,3-thiazole-4-carboxylic acid in 1.2 ml of DMF were added 117 mg of 2-amino-N-pyridin-3-yl benzamide, 110 mg of WSC-HCl, and 100 mg of HOBt, followed by stirring at 60C for 3 days. To the reaction liquid was added an aqueous sodium hydrogen carbonate solution, and the resulting insoluble materials were collected by filtration. This was washed with acetonitrile to prepare 195 mg of 2-[methyl(tetrahydro-2H-pyran-4-ylmethyl)amino]-N-[2-(pyridin-3-ylcarbamoyl)phenyl]-1,3-thiazole-4-carboxamide.

The synthetic route of 76102-92-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Astellas Pharma Inc.; EP2206707; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

So far, in addition to halogen atoms, other non-metallic atoms can become part of the aromatic heterocycle, and the target ring system is still aromatic.Hierlmeier, Gabriele; Wolf, Robert researched the compound: Palladium(II) acetate( cas:3375-31-3 ).Electric Literature of C4H6O4Pd.They published the article 《Bulking up CpBIG: a penta-terphenyl cyclopentadienyl ligand》 about this compound( cas:3375-31-3 ) in ChemRxiv. Keywords: potassium pentaterphenylcyclopentadienyl sandwich complex preparation crystal structure; crystal structure lithium potassium pentaterphenylcyclopentadienyl sandwich complex; mol structure lithium potassium pentaterphenylcyclopentadienyl sandwich complex; lithium pentaterphenylcyclopentadienyl sandwich complex preparation crystal structure; sodium pentaterphenylcyclopentadienyl sandwich complex preparation; rubidium pentaterphenylcyclopentadienyl sandwich complex preparation; cesium pentaterphenylcyclopentadienyl sandwich complex preparation. We’ll tell you more about this compound (cas:3375-31-3).

The modification of cyclopentadienyl ligands with carefully selected substituents is a widely used strategy to tune their steric and electronic properties. The authors describe the synthesis of an extremely bulky penta-terphenyl cyclopentadienyl ligand (CpT5) by arylation of cyclopentadiene. Deprotonation reactions with various Group 1 metals and bases afforded a complete series of alkali metal salts MCpT5 with M = Li to Cs. The compounds were isolated as solvate-free salts, which were characterized by multinuclear NMR spectroscopy, UV-visible spectroscopy and elemental anal. Single-crystal x-ray diffraction studies on LiCpT5, NaCpT5 (crystallized as a solvate with one THF mol. per formula unit) and KCpT5 revealed the formation of metallocene-like sandwich structures in the solid state.

《Bulking up CpBIG: a penta-terphenyl cyclopentadienyl ligand》 provides a strategy for the preparation of materials with excellent comprehensive properties, which is conducive to broaden the application field of this compound(Palladium(II) acetate)Electric Literature of C4H6O4Pd.

Reference:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

The chemical properties of alicyclic heterocycles are similar to those of the corresponding chain compounds. Compound: 8-Bromooctan-1-ol, is researched, Molecular C8H17BrO, CAS is 50816-19-8, about Design and synthesis of α-naphthoflavone chimera derivatives able to eliminate cytochrome P450 (CYP)1B1-mediated drug resistance via targeted CYP1B1 degradation, the main research direction is alpha naphthoflavone conjugates CYP1B1 degradation drug resistance prostate cancer; CYP1B1; Click reaction; PROTACs; Reversal of drug resistance; α-Naphthoflavone-based conjugates.Computed Properties of C8H17BrO.

Extrahepatic cytochrome P 450 1B1 (CYP1B1), which is highly expressed in various tumors, is an attractive and potential target for cancer prevention, therapy, and reversal of drug resistance. CYP1B1 inhibition is the current predominant therapeutic paradigm to treating CYP1B1-mediated malignancy, but therapeutic effect has little success. Herein, we reported CYP1B1 degradation in place of CYP1B1 inhibition for reversing drug resistance toward docetaxel in CYP1B1-overexpressing prostate cancer cell line DU145 using a PROTAC strategy. Replacing chlorine atom of a CYP1B1 selective inhibitor we found previously with ethynyl, we got the resulting α-naphthoflavone derivative 5 which kept strong inhibition against CYP1B1 (IC50 = 0.4±0.2 nM) and high selectivity. Coupling of 5 with thalidomide derivatives of varying chain lengths afforded conjugates 6A-6D via click reaction. In vitro cell-based assay indicated that 6C was more effective in eliminating drug resistance of CYP1B1-overexpressed DU145 cells compared with other analogs. Western blotting anal. showed CYP1B1 degradation was one main reason for the reversal of drug resistance to docetaxel and the effect was obtained in a concentration-dependent manner. This work is the first attempt to overcome CYP1B1-mediated drug resistance via CYP1B1 degradation instead of CYP1B1 inhibition, which could provide a new direction toward eliminating drug resistance.

《Design and synthesis of α-naphthoflavone chimera derivatives able to eliminate cytochrome P450 (CYP)1B1-mediated drug resistance via targeted CYP1B1 degradation》 provides a strategy for the preparation of materials with excellent comprehensive properties, which is conducive to broaden the application field of this compound(8-Bromooctan-1-ol)Computed Properties of C8H17BrO.

Reference:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem