Tag: M.W:100-200

Reference of 143426-49-7,Some common heterocyclic compound, 143426-49-7, name is (4-Pyrazol-1-yl-phenyl)methanol, molecular formula is C10H10N2O, 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 suspension of (4-(1H-pyrazol-1-yl)phenyl)methanol (22.5 g) in acetonitrile (500 mL) was added N-fluoro-N’-(chloromethyl)triethylenediamine bis(tetrafluoroborate) (108 g) at room temperature, and the mixture was stirred at 80C for 16 hr. The reaction solution was diluted with ethyl acetate, washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated. The residue was purified by silica gel chromatography (petroleum ether-ethyl acetate) to give the title compound (4.5 g). 1H NMR (400 MHz, CDCl3) delta 4.73 (2H, s), 7.45 (2H, d, J = 8.0 Hz), 7.57 (1H, d, J = 4.0 Hz), 7.61 (2H, d, J = 8.0 Hz), 7.80 (1H, d, J = 4.8 Hz).

The synthetic route of 143426-49-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Takeda Pharmaceutical Company Limited; SUGIMOTO, Takahiro; NAKAMURA, Minoru; SAKAMOTO, Hiroki; SUZUKI, Shinkichi; YAMADA, Masami; KAMATA, Makoto; KOJIMA, Takuto; FUJIMORI, Ikuo; SHIMOKAWA, Kenichiro; EP2921480; (2015); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 150712-24-6,Some common heterocyclic compound, 150712-24-6, name is 5-Benzyl-1H-pyrazol-3-amine, molecular formula is C10H11N3, 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.

EXAMPLE 40 3-[(5-Benzyl-2H-pyrazol-3-ylamino)-methylene]-1,3-dihydro-indol-2-one The named compound is prepared by substituting 5-benzyl-2H-pyrazol-3-ylamine for 3-aminopyrazole in the reaction of Example 1. Specifically, E & Z-3-[(hydroxy)-methylene]-1,3-dihydro-indol-2-one (0.100 gms.) is reacted with 0.231 gms. 5-benzyl-2H-pyrazol-3-ylamine by refluxing in tetrahydrofuran (2.5 mL) overnight.

The synthetic route of 150712-24-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Allergan, Inc.; US6559173; (2003); B1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 132274-70-5,Some common heterocyclic compound, 132274-70-5, name is 1-Phenyl-1H-pyrazole-5-carbaldehyde, molecular formula is C10H8N2O, 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.

Example B: 4-Brom-1-phenylpyrazole-5-carbaldehyd-dimethylacetal [Show Image] Experimental procedure: The aldehyde (B) (2.30 g, 13.4 mmol), trimethylortoformiate (4.4 mL, 40.1 mmol) and p-toluolsulfonic acid monohydrate (127.1 mg, 0.67 mmol) were dissolved in abs. methanol (260 mL). After slow addition of pyridiniumbromide-perbromide (PBB) (4.3 g, 13.4 mmol) the solution was stirred for 90 h at room temperature. Subsequently a saturated NaHCO3-Solution (25 mL) was added, diluted with water and 3x extracted with CH2Cl2. The organic phases were dried (K2CO3) and the solvent removed under vacuum. The crude product (4.08 g) was purified using flash-chromatography (?=8 cm, h = 12 cm, n-hexane:ethylacetate = 9:1, 40 mL, Rf = 0.20). Colourless solid, melting point: 33 C, yield: 3.67 g (93%) C12H13BrN2O2 (297.2); MS (EI): m/z (rel. Int.) = 298 [82Br-M+, 28], 296 [79Br-M+, 25], 267 [82Br-M- OCH3, 93], 265 [79Br-M – OCH3, 100], 235 [82Br-M- 2x OCH3, 49], 233 [79Br-M – 2x OCH3, 47]. IR (neat): nu (cm-1) = 3062 (C aromat.), 2933 (C-H aliphat.), 2830 (C-H), 1597, 1501 (C=C), 1090, 1065 (C-O), 761, 692 (C-H). 1H-NMR (CDCl3): delta (ppm) = 3.37 (s, 6 H, ArCH(OCH3)2), 5.36 (s, 1 H, ArCH(OCH3)2), 7.39 – 7.49 (m, 3 H, Phenyl-CH), 7.53 – 7.59 (m, 2 H, Phenyl-CH, ortho), 7.63 (s, 1 H, Pyrazole-3CH). 13C-NMR (CDCl3): delta (ppm) = 54.7 (2 C, ArCH(OCH3)2), 95.9 (1 C, Pyrazole-4-C), 98.5 (1 C, ArCH(OCH3)2), 125.6 (2 C, Phenyl-CH, ortho), 128.7 (1 C, Phenyl-CH, para), 129.1 (2 C, Phenyl-CH, meta), 136.3 (1 C, Phenyl-C, quartaer), 140.1 (1 C, Pyrazole-5-C), 141.2 (1 C, Pyrazole-3-CH).

The synthetic route of 132274-70-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Laboratorios del Dr. Esteve S.A.; EP1982987; (2008); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

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. 73981-23-4, name is Ethyl 3-ethyl-1H-pyrazole-4-carboxylate, A new synthetic method of this compound is introduced below., name: Ethyl 3-ethyl-1H-pyrazole-4-carboxylate

Ethyl 5-ethyl-l-(4-methoxybenzyl)-lH-pyrazole-4-carboxylate and ethyl 3-betathyl-l-(4- methoxybenzyl)- 1 H-pyrazole-4-carboxylateAccording to Scheme 9 Step 3: A suspension of ethyl 3-ethyl-lH-pyrazole-4- carboxylate (5.95 mmol, 1.0 g), l-(chloromethyl)-4-methoxybenzene (6.54 mmol, 0.89 mL) and K2CO3 (17.8 mmol, 2.46 g) in acetone (20 mL) was heated at 600C overnight. After evaporation of the solvent, water was added and the aqueous phase was extracted with DCM. The organic phase was dried over Na2SOzI, was filtered and was concentrated under reduced pressure. The crude product was purified by flash chromatography over silica gel using cyclohexane/AcOEt (95:5) as eluent to afford a mixture of ethyl 5-ethyl-l-(4-methoxybenzyl)-lH-pyrazole-4-carboxylate and of ethyl 3-ethyl-l-(4-methoxybenzyl)-lH-pyrazole-4-carboxylate (2.77 mmol, 800 mg, 47%) as a yellow oil.LC (Zorbax SB-Ci8, 3.5mum, 4.6x30mm Column): RT = 2.58 min.

The synthetic route of 73981-23-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Addex Pharma S.A.; WO2009/10455; (2009); A2;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 143426-49-7, 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. 143426-49-7, name is (4-Pyrazol-1-yl-phenyl)methanol belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a stirred solution of 4-(1 H-pyrazol-1 -yl)phenyl)methanol (0.2 g, 1.14 mmol) in DCM (10 mL), SOCI2 (0.2 mL, 2.29 mmol) was added at 0 C and the reaction mixture was stirred for 2 h. After completion of reaction, the reaction mixture was concentrated under vacuum and co-distilled with DCM to get the title compound. It was used in the next step without further purification. Yield: (0.170 g, brown gummy solid). LCMS: (Method A) 193.1 (M+H), Rt. 3.46 min, 94.32% (Max).

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, (4-Pyrazol-1-yl-phenyl)methanol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ASCENEURON S. A.; QUATTROPANI, Anna; WISHART, Grant; KULKARNI, Santosh S.; RAKESH, Paul; (338 pag.)WO2020/39027; (2020); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 128694-63-3, name is 1-Methyl-3-(trifluoromethyl)-1H-pyrazole-5-carboxylic acid, molecular formula is C6H5F3N2O2, 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. SDS of cas: 128694-63-3

BB4; 5-(chloromethyl)-l-methyl-3-(trifluoromethyl)-lH-pyrazoleBB4a BB4b BB4Step A: l-Methyl-3-(trifluoromethyl)-lH-pyrazole-5-carboxylic acid BB4a (837 mg, 4.3 mmol) is dissolved in anhydrous tetrahydrofurane (10 mL), then LiAlH4 (2.16 mL of 2.0 M in tetrahydrofurane, 4.3 mmol) is added dropwise and stirred at rt for lh. The mixture is quenched by dropwise addition of IN HC1, then is made basic by addition of saturated NaHC03 and extracted with EtOAc (3x). The organic layers are combined, washed with brine, dried (MgS04), filtered and concentrated to provide (l-methyl-3-(trifluoromethyl)- lH-pyrazol-5-yl)methanol BB4b as a clear oil. 1H NMR (400 MHz, CDC13) delta = 6.46 (s, 1H), 4.69 (d, J = 5.6 Hz, 2H), 3.95 (s, 3H); MS calcd. for C6H8F3N20 ([M+H]+): 181.0, found: 181.1.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 128694-63-3, its application will become more common.

Synthetic Route of 128694-63-3, A common heterocyclic compound, 128694-63-3, name is 1-Methyl-3-(trifluoromethyl)-1H-pyrazole-5-carboxylic acid, molecular formula is C6H5F3N2O2, 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.

EXAMPLE 2 N-[5-(2-chloro-6-fluorophenyl)-1H-pyrazol-3-yl]-1-methyl-3-(trifluoromethyl)-1H-pyrazole-5-carboxamide [0113] Compound of Preparation 11 (100 mg, 0.19 mmol) and 1-methyl-3-(trifluoromethyl)-1 H-pyrazole-5-carboxylic acid (91 mg, 0.47 mmol) were dissolved in 1.5 mL DMF. N-(3-Dimethylaminopropyl)-N’-ethylcarbodiimide hydrochloride 98% (144 mg, 0.75 mmol) and 1-Hydroxybenzotriazole hydrate (102 mg, 0.75 mmol) were added and the mixture was stirred at room temperature overnight. Ethyl acetate was added and the organic phase was washed with water two times, NaOH 1 N two times, dried over MgSO4 and evaporated under reduced pressure and the residue was purified using the Isolera purification (ethyl acetate – hexane gradient, 0:100 rising to 100:0) to give 35 mg (0.09 mmol, 19%) of the title compound as a white solid. LRMS (m/z): 388 (M+1)+. 1 H NMR (300 MHz, DMSO-d6) d ppm 4.19 (3 H, s), 6.86 (1 H, s), 7.31 – 7.61 (3 H, m), 7.65 (1 H, s), 11.24 (1 H, br. s), 12.97 (1 H, br. s)

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Adding a certain compound to certain chemical reactions, such as: 304693-70-7, name is 1-(2-Methoxyethyl)-1H-pyrazole-4-carbaldehyde, belongs to pyrazoles-derivatives compound, 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 304693-70-7, Product Details of 304693-70-7

In a sealed tube, under N2, intermediate 35 (211 mg; 1.37 mmol) and Ti(OiPr)4 (436 jiL; 1.83 mmol) were added to a solution of intermediate 11(300mg; 0.914 mmol) in THF(6 mL). The solution was stirred at 50C for 5 hours then at rt overnight. The reaction mixture was cooled to 5C and isopropyl magnesium chloride 2M in THF (2.28 mL; 4.57 mmol) was added dropwise. The reaction mixture was allowed to rise slowly to rt and stirred overnight. The reaction mixture was diluted with EtOAc and poured onto a 10% aqueous solution of K2C03. The precipitate was removed by filtration over Celite. Theorganic layer was decanted, washed with brine, dried over MgSO4, filtered and evaporated to dryness. The residue was purified by chromatography over silica gel (irregular SiOH, 40g; mobile phase: gradient from 0% MeOH, 100% DCM to 10% MeOH, 90% DCM). The fractions containing the product were collected and evaporated to dryness to give 0.337 g of an intermediate residue which was purified again bychromatography via reverse phase (stationary phase: YMC-actus Triart C18 lOjim30*150mm, mobile phase: gradient from 55% NH4HCO3 0.2%, 45% ACN to 0%NH4HCO3 0.2%, 100% ACN). The pure fractions were collected and evaporated todryness. The residue was freeze-dried with acetonitrile/water 20/80 to afford 120 mg(26%) of compound 71.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-(2-Methoxyethyl)-1H-pyrazole-4-carbaldehyde, and friends who are interested can also refer to it.

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. 19959-77-4, name is 2-(5-Methyl-1H-pyrazol-3-yl)pyridine, A new synthetic method of this compound is introduced below., category: pyrazoles-derivatives

Solid ligand L (0.2mmol, 31.8mg) and Cd(NO3)2·4H2O (0.1mmol, 30.8mg) were placed into the bottom of separate arms of an H-tube. The H-tube was filled with acetonitrile solution and sealed with plastic film. After one week, colorless stick-like crystals of compound 4 were generated and collected, washed with n-hexane 2-3 times, then dried in vacuum. Yield: 42.72mg (77%), M. p. > 300C. Anal. Calc. for C18H18CdN8O6 (FW, 554.8): C, 38.97; H, 3.27; N, 20.20. Found: C, 38.31; H, 3.39; N, 19.70%. Selected IR data (cm-1, KBr): 3200 (b, s), 3135 (s), 2994 (s), 2853 (m), 2363 (s), 1607 (m) (nu(C=N)), 1578 (m) (nu(C=C)), 1435 (s), 1387 (s), 1340 (m), 1301 (m), 1225 (w), 1156 (w), 1111 (w), 1018 (w), 980 (s), 797 (s), 740 (m).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

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. 873191-23-2, name is 5-(Bromomethyl)-1,3-dimethyl-1H-pyrazole, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C6H9BrN2

General procedure: The phenanthridine skeletons1-8 (0.1 mmol) were dissolved in dryTHF (10 mL), and NaH (50 mg, 2 mmol), and 3-(bromomethyl)pyridine,3-(chloromethyl)-1,5-dimethyl-1H-pyrazole or 5-bromomethyl-1,3-dimethyl-1H-pyrazole (1 mmol) were added. The mixture was stirred atrt. for 12 h and quenched with H2O (50 mL) in an ice bath. The solutionwas evaporated to remove the THF and extracted with CH2Cl2(2×30 mL). The organic layer was washed with saturated NaHCO3 andbrine, dried over MgSO4, filtered and concentrated. The residue waspurified by column chromatography using petroleum-EtOAc as theeluent to afford about 35 mg of each phenanthridine compound.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 873191-23-2.