Tag: M.W:100-200

Synthetic Route of 3398-16-1, A common heterocyclic compound, 3398-16-1, name is 4-Bromo-3,5-dimethylpyrazole, molecular formula is C5H7BrN2, 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.

General procedure: Ethyl 5-(chloromethyl)furan-2-carboxylate (5a, 2.0 g, 10.60 mmol) was added to a solution of 3,5-dimethyl-1H-pyrazole (6a) (1.019 g, 10.60 mmol), KOtBu (1.547 g, 13.79 mmol) and TBAI (0.392 g, 1.060 mmol) in THF (53 ml) at 0 °C. The mixture was allowed to warm up to rt and was stirred at rt for 24 h. To the reaction mixture was added satd NH4Cl aq, and then the mixture was extracted with EtOAc. The organic layers were combined, washed with H2O and brine, dried over Na2SO4, and concentrated in vacuo. The residue was subjected to silica gel column chromatography (hexane/EtOAc), which yielded the pyrazole 7a (1.25 g, 47.5percent) as a brown oil. Pyrazoles 7b?e were synthesized in a similar way.

The synthetic route of 3398-16-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Yasuda, Yorinobu; Arakawa, Takeaki; Nawata, Yumi; Shimada, Sayaka; Oishi, Shinya; Fujii, Nobutaka; Nishimura, Shinichi; Hattori, Akira; Kakeya, Hideaki; Bioorganic and Medicinal Chemistry; vol. 23; 8; (2015); p. 1776 – 1787;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 5932-27-4,Some common heterocyclic compound, 5932-27-4, name is Ethyl 1H-pyrazole-3-carboxylate, molecular formula is C6H8N2O2, 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.

Description 11: 1-tert-Butoxvcarbonvlmethvl-1 H-pvrazole-4-carboxylic acid ethyl ester Potassium tert butoxide (0.045g) was added, in portions, to a stirred solution of 3- (ethoxycarbonyl) pyrazole [CAS 37622-90-5] (0.050g) in N, N- dimethylformamide (0. 5mol). The mixture was stirred for 5 min then tert- butylbromoacetate (0.078g) was added, in portions over 2 min. The mixture was stirred for 0.75h then partitioned between ethyl acetate (30moi) and 1. 0M aqueous sodium bicarbonate (20ml). The organic phase was separated, washed with water (2x20m1), dried (Na2SO4) and concentrated in vacuo to give the title compound (0.073g) as a colourless, viscous oil. LC-MS: Rt = 2.78min. Mass Spectrum m/z 255 [MH+]

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Ethyl 1H-pyrazole-3-carboxylate, its application will become more common.

Reference:
Patent; GLAXO GROUP LIMITED; WO2003/82862; (2003); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 3273-44-7, These common heterocyclic compound, 3273-44-7, name is 5-Methyl-1H-pyrazole-3-carbaldehyde, 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.

General procedure: To a suspension of 5-methyl-1H-pyrazole-3-carbaldehyde (18; 2-6 equiv) in anhydrous THF (10 mL) (in the case of the synthesis of 1) or MeOH (in the case of the synthesis of 2-5 and 11), the corresponding derivative bearing one to three amino groups (17,21 25-289d,11 or 36,4c see Scheme 1 and Scheme 2) (1 equiv), dissolved in anhydrous MeOH (5 mL), was added. The resulting mixture was heated at reflux until a clear solution resulted and then stirred at r.t. (up to 4 days, TLC analysis). The resulting imines were reduced without further purification by addition of NaBH4 (3-9 equiv) in portions. After complete addition of the reducing agent, the reaction mixture was stirred for 24 h at r.t. and then the solvent was removed under reduced pressure. The residue was suspended in CHCl3-H2O (1:1, 10 mL) and stirred for 12 h at r.t. The resulting suspension was extracted with CHCl3 (3 × 20 mL), dried over MgSO4, and the solvent was removed. The crude product was purified by column chromatography.

Statistics shows that 5-Methyl-1H-pyrazole-3-carbaldehyde is playing an increasingly important role. we look forward to future research findings about 3273-44-7.

Reference:
Article; Koch, Niklas; Seichter, Wilhelm; Mazik, Monika; Synthesis; vol. 48; 17; (2016); p. 2757 – 2767;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 1254717-53-7, 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. 1254717-53-7 name is (5-(Trifluoromethyl)-1H-pyrazol-3-yl)methanamine, This 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.

(3-(Trifluoromethyl)-1 H-pyrazol-5-yl)methanamine (0.7 g, 4.2 mmol, 1 eq) was charged in dichloromethane (70 ml) at room temperature, then to that TEA (.42g, 4.2 mmol, 1eq ) was added at room temperature and stirred for 10 min and cooled to 0-5C. (Boc)20 (0.92 g, 4.2 mmol, 1 eq) was added drop wise to reaction mixture for 30 min and maintained for 3 h at 0-5C. Progress of the reaction was monitored by the TLC (30 % Ethyl acetate/Hexane). On completion of the reaction, dichloromethane was distilled, the residue obtained was treated water (50 ml) and extracted with ethyl acetate (100 ml). The combined organic layer was dried over sodium sulphate, distilled the solvent under vacuum. The obtained crude was purified with column chromatography to yield the required product as a white colored solid (0.5 g, 44 % yield).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, (5-(Trifluoromethyl)-1H-pyrazol-3-yl)methanamine, and friends who are interested can also refer to it.

Reference:
Patent; GRUeNENTHAL GMBH; FRANK, Robert; CHRISTOPH, Thomas; LESCH, Bernhard; LEE, Jeewoo; WO2012/62462; (2012); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 3469-69-0, name is 4-Iodopyrazole, 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 3469-69-0, HPLC of Formula: C3H3IN2

To a mixture of 4-iodo-1H-pyrazole (2.91 g, 15 mmol), Pd(PPh3)2C12 (1 g, 1.5 mmol), CuT (286 mg, 1.5 mmol) and Et3N (6 mL) in EtOH (20 mL) was added trimethylsilylacetylene (3.2 mL, 22.5 mmol). The reaction was stirred at 70C for 4 h, then cooled to rt and concentratedvacuo. The residue was diluted with EtOAc (20 mL) and the undissolved solid was removed by filtration. The filtrate was dried over Na2504 and concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (v/v) = 5/1) to give the title compound as a white solid (1.3 g, 53%).LC-MS (ESI, pos. ion) m/z: 165 [M + H]1H NMR (400 MHz, CDC13) 5 (ppm): 0.24 (s, 9H), 7.76 (s, 2H), 11.43 (br, 1H).

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-Iodopyrazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; XI, Ning; SUNSHINE LAKE PHARMA CO., LTD.; YIN, Lihua; LI, Xiaobo; YU, Na; WU, Yanjun; WO2013/177092; (2013); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

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. 5071-61-4, name is 5-Phenyl-1H-pyrazole-3-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 5071-61-4

A solution of acid 4 (0.09 g, 0.47 mmol) in dry DMF (2 mL) treated sequentially with amine (5a-i, 6a-e and 7a-h; 0.517 mmol)and triethylamine (0.94 mmol) was stirred under a N2 atmosphere for 15 min, later TBTU (0.56 mmol) was added and reaction mixture refluxed for 4-10 h. The reaction mixture was quenched with aq satd NH4Cl solution (10 mL). After 10 min, it was diluted withCHCl3 (2 10 mL) and washed with water (10 mL), NaHCO3 solution(10 mL) and brine (10 mL). The organic layers were dried over anhydrous sodium sulfate, evaporated and the residue purified by column chromatography using 30% ethyl acetate in pet. ether to afford corresponding amides 8a-i, 9a-e and 10a-h.

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 5071-61-4.

Reference:
Article; Doma, Anuradha; Kulkarni, Ravindra; Palakodety, Radhakrishna; Sastry, G. Narahari; Sridhara, Janardhan; Garlapati, Achaiah; Bioorganic and Medicinal Chemistry; vol. 22; 21; (2014); p. 6209 – 6219;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 75415-03-1,Some common heterocyclic compound, 75415-03-1, name is 2-(1H-Pyrazol-3-yl)pyridine, molecular formula is C8H7N3, 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 solution of 2-(1H-pyrazole-3-yl)pyridine (3.02 g, 20.80 mmol) and NBS (3.72 g, 20.90 mmol) in DMF (30 mL) was stirred for 2 h in an ice bath. The reaction mixture was poured into ice water, filtered, and dried in vacuo. The residue (4.38 g, 95% yield) as a white solid was reacted without further purification. 1H-NMR (270 MHz, CDCl3) delta: 11.46 (1H, br s), 8.63-8.65 (1H, m), 8.29 (1H, d, J = 8.4 Hz), 7.78-7.85 (1H, m), 7.64 (1H, s), 7.28-7.33 (1H, m). LC/MS (ESI): m/z 223 [M + H]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-(1H-Pyrazol-3-yl)pyridine, its application will become more common.

Reference:
Article; Sekimata, Katsuhiko; Sato, Tomohiro; Sakai, Naoki; Watanabe, Hisami; Mishima-Tsumagari, Chiemi; Taguri, Tomonori; Matsumoto, Takehisa; Fujii, Yoshifumi; Handa, Noriko; Honma, Teruki; Tanaka, Akiko; Shirouzu, Mikako; Yokoyama, Shigeyuki; Miyazono, Kohei; Hashizume, Yoshinobu; Koyama, Hiroo; Chemical and Pharmaceutical Bulletin; vol. 67; 3; (2019); p. 224 – 235;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 5203-77-0, 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. 5203-77-0 name is 1,3-Dimethyl-1H-pyrazol-5-ol, This 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.

General procedure: To a flame-dried Schlenk tube was added electron-rich aromatic (0.5mmol), CF3SO2Na (118mg, 0.7mmol) dry 1,4-dioxane or CH3CN (1mL). The mixture was heated to 60C by a preheated oil bath. PhPCl2 (125mg, 0.7 mmoL) was added. The reaction mixture was stirred at 70C for the indicated time. Then the reaction mixture was cooled to room temperature. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography to afford the pure product.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1,3-Dimethyl-1H-pyrazol-5-ol, and friends who are interested can also refer to it.

Reference:
Article; Zhao, Xia; Zheng, Xiancai; Tian, Miaomiao; Sheng, Jianqiao; Tong, Yifan; Lu, Kui; Tetrahedron; vol. 73; 51; (2017); p. 7233 – 7238;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

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. 151049-87-5, name is 3-Bromo-1-methyl-1H-pyrazole, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 151049-87-5

(2,6-Difluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanol (6.0 g, 22.2 mmol, 1.0 eq.), 3-bromo-1-methyl-1H-pyrazole (4.29 g, 26.7 mmol, 1.2 eq.), potassium carbonate (6.23 g, 44.4 mmol, 2.0 eq.) and tetrakis(triphenylphosphine)palladium(0) (487 mg, 0.67 mmol, 0.03 eq.) were combined into a reaction flash under an inert atmosphere. Degassed 1,4-dioxane (92.5 mL) and water (18.5 mL) were added. After 16 h at 100 C., the reaction mixture was diluted with water and extracted with IPA/CHCl3 (1:3) (3*). The combined organic extracts were concentrated under reduced pressure. Purification using flash column chromatography on silica gel with 0-70% MeCN/DCM provided the title compound (3.9 g, 78% yield). 1H-NMR (400 MHz, DMSO-d6) 7.77 (d, J=2.3 Hz, 1H), 7.48-7.42 (m, 2H), 6.83 (d, J=2.3 Hz, 1H), 5.22 (t, J=5.6 Hz, 1H), 4.49 (d, J=5.5 Hz, 2H), 3.88 (s, 3H); ES-MS [M+H]+=225.4.

According to the analysis of related databases, 151049-87-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Vanderbilt University; Lindsley, Craig W.; Conn, P. Jeffrey; Engers, Darren W.; Engers, Julie L.; Long, Madeline; Bender, Aaron M.; US2020/131180; (2020); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 309740-49-6, 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. 309740-49-6 name is Methyl 1-methyl-4-nitro-1H-pyrazole-5-carboxylate, This 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.

General procedure: To a solution of 15a (3.57 g, 16.8 mmol) in MeOH (60 mL) wasadded Pd/C (50% wet, 0.178 g), and the mixture was stirred at room temperature for 2 h under hydrogen atmosphere. The insolublematerials were filtered off by using a pad of Celite, and the Celitewas washed with MeOH. The filtrate was concentrated in vacuo.The residue was diluted with EtOAc, washed with brine, dried overMgSO4, and filtered. The filtrate was concentrated in vacuo toafford 16a

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 1-methyl-4-nitro-1H-pyrazole-5-carboxylate, and friends who are interested can also refer to it.

Reference:
Article; Kojima, Takuto; Asano, Yasutomi; Kurasawa, Osamu; Hirata, Yasuhiro; Iwamura, Naoki; Wong, Tzu-Tshin; Saito, Bunnai; Tanaka, Yuta; Arai, Ryosuke; Yonemori, Kazuko; Miyamoto, Yasufumi; Sagiya, Yoji; Yaguchi, Masahiro; Shibata, Sachio; Mizutani, Akio; Sano, Osamu; Adachi, Ryutaro; Satomi, Yoshinori; Hirayama, Megumi; Aoyama, Kazunobu; Hiura, Yuto; Kiba, Atsushi; Kitamura, Shuji; Imamura, Shinichi; Bioorganic and Medicinal Chemistry; vol. 26; 9; (2018); p. 2452 – 2465;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics