Category: 179692-08-1

Some common heterocyclic compound, 179692-08-1, name is Ethyl 4-iodo-1H-pyrazole-5-carboxylate, molecular formula is C6H7IN2O2, 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. Recommanded Product: Ethyl 4-iodo-1H-pyrazole-5-carboxylate

At 0C, NaH (902.12 mg, 22.55 mmol, 60%) was added portionwise into a solution of Example 1A (5 g, 18.79 mmol) in DMF (30 mL) and stirred for 30 min. A solution of dibromodifluoromethane (9.00 g, 42.89 mmol) in DMF (30 mL) was added and stirred at 20C for 16 h. The reaction solution was quenched with water (100 mL) and extracted with ethyl acetate (50 mL * 3). The combined organic phase was washed with brine (100 mL), dried over anhydrous sodium sulfate, filtered and evaporated to give a residue. The residue was purified by column chromatography to give the title compound as a brown liquid (2 g, 26.95%). 1H NMR (400 MHz, CHLOROFORM-d) delta=8.00 (s, 1H), 4.48 (q, J=7.3 Hz, 2H), 1.45 (t, J=7.2 Hz, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 179692-08-1, its application will become more common.

Reference:
Patent; Chai Tai Tianqing Pharmaceutical Group Co., Ltd.; Medshine Discovery Inc.; LIU, Shilan; WANG, Dahai; LIANG, Guibai; HU, Guoping; LI, Jian; CHEN, Shuhui; (167 pag.)EP3418282; (2018); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

179692-08-1, name is Ethyl 4-iodo-1H-pyrazole-5-carboxylate, belongs to pyrazoles-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Quality Control of Ethyl 4-iodo-1H-pyrazole-5-carboxylate

Example 15, Step C [00154] To a solution of compound 15c (38 g, 143 mmol) in acetonitrile (380 mL) at r.t. was added K2C03 (39.5 g, 286 mmol) and then PMBCI (24 mL, 177 mmol). The reaction mixture was stirred at 60C overnight. After cooling to r.t., the mixture was filtered and concentrated under reduced pressure. The residue was purified by chromatography on silica gel to afford compound 15d (32 g, 58%).[00155] This compound was characterized by proton NMR (1HNMR) and mass spectroscopy (MS) in accordance with the procedures described herein. Proton NMR yielded the following results: 1H NMR (DMSO-d6, 400MHz): delta 8.13(s, 1 H), 7.23(d, J = 8.8 Hz, 2H), 6.90(d, J = 8.8 Hz, 2H), 5.29(s, 2H), 4.24 (q, J = 6.8 Hz, 2H), 3.71 (s, 3H); 1.26(t, J = 6.8 Hz, 3H). Mass spectroscopy indicated MS (ESI): m/z 387 (M+H)+.

The synthetic route of 179692-08-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; ADDEX PHARMA SA; LIVERTON, Nigel, J.; BOLEA, Christelle; CELANIRE, Sylvain; LUO, Yunfu; WO2012/6760; (2012); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 179692-08-1, A common heterocyclic compound, 179692-08-1, name is Ethyl 4-iodo-1H-pyrazole-5-carboxylate, molecular formula is C6H7IN2O2, 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.

NaH (60% dispersion in mineral oil, 0.72 g, 18 mmol, 1.2 eq) was added in portions to a mixture of ethyl 4-iodo-1H-pyrazole-3-carboxylate (4.2 g, 15 mmol, 1.0 eq) and anhydrous THF (15 mL) at 0C. Once addition of NaH was complete, the mixture was stirred for an additional 30 min at 0C and 1h at RT. The mixture was re-cooled to 0C and then MeI (1.0 mL, 16.5 mmol, 1.1 eq) was added. When the reaction mixture solidified, the cold bath was removed and the mixture was maintained at RT for 1h. When the starting material was consumed as judged by analytical HPLC, H2O (0.5 mL) was added slowly to quench the reaction and then NaOH solution (2 M, 1.0 eq) was added slowly with stirring. The mixture was stirred at rt until hydrolysis of the ester was complete (1-2 h). The light-yellow suspension was filtered and the resulting yellow solid was collected. The filtrate was concentrated in vacuo and then washed with hexanes to remove the mineral oil. The resulting aqueous layer and solid were combined and acidified with 6N HCl to pH 12. The aqueous was extracted with EtOAc (3x). The combined organics were washed with brine, dried (Na2SO4), and concentrated to afford the title acid as a pale yellow solid that was used without further purification.

The synthetic route of 179692-08-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; EOLAS THERAPEUTICS, INC.; KAMENECKA, Theodore, M.; HOLENZ, Joerg; WESOLOWSKI, Steven; HE, Yuanjun; BUeRLI, Roland; (201 pag.)WO2017/139603; (2017); 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. 179692-08-1, name is Ethyl 4-iodo-1H-pyrazole-5-carboxylate, A new synthetic method of this compound is introduced below., Safety of Ethyl 4-iodo-1H-pyrazole-5-carboxylate

60% sodium hydride (99 mg) was added to a solution of the compound 0215-2 (0.50 g) and iodomethane (0.23 mL) in tetrahydrofuran (2.0 mL) at 0C, and the mixture was stirred at room temperature for 0.5 hours. To the reaction solution, a saturated aqueous ammonium chloride solution was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine and then dried over sodium sulfate. The solvent was removed under reduced pressure and the obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate) to obtain a compound 0215-2 (0.37 g) as a colorless oily substance. – Synthesis of Compound 0219 – (Synthesis of Compound 0219-1) The same method as in Example 215 except for using (2-(trimethylsilyl)ethoxy)methyl chloride instead of iodomethane used for the synthesis of the compound 0215-2 in Example 215 was used to obtain a compound 0219-1 (0.273 g) as a position isomer mixture (colorless oily substance). (Synthesis of Compound 0219-2) The same method as in Example 214 except for using the compound 0219-1 instead of tert-butyl 4-(4-iodo-1H-pyrazol-1-yl)piperidine-1-carboxylate used for the synthesis of the compound 0214-2 in Example 214 was used to obtain a compound 0219-2 (0.22 g) as a position isomer mixture (pale yellow solid). MS m/z (M+H): 525. A 1 M aluminum lithium hydride solution in diethylether (24 muL) was added to a solution of the compound 0215 (5.0 mg) in tetrahydrofuran (1.0 mL) at room temperature, and the mixture was stirred for 0.5 hours. To the reaction solution, a saturated aqueous ammonium chloride solution and methanol were added, and the solvent was removed under reduced pressure. The obtained residue was purified by silica gel column chromatography (chloroform-methanol) to obtain a compound 0216 (4.5 mg). (Synthesis of Compound 0219-3) The same method as in Example 216 except for using the compound 0219-2 instead of the compound 0215 used for the synthesis of the compound 0216 in Example 216 was used to obtain a compound 0219-3 (59 mg) as a position isomer mixture (brown solid). MS m/z (M+H): 483.

The synthetic route of 179692-08-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FUJIFILM Corporation; FURUYAMA, Hidetomo; KURIHARA, Hideki; FURUYA, Kentarou; TERAO, Takahiro; SEKINE, Shinichirou; NAKAGAWA, Daisuke; EP2727920; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 179692-08-1, 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. 179692-08-1, name is Ethyl 4-iodo-1H-pyrazole-5-carboxylate belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Example 15, Step C [00154] To a solution of compound 15c (38 g, 143 mmol) in acetonitrile (380 mL) at r.t. was added K2C03 (39.5 g, 286 mmol) and then PMBCI (24 mL, 177 mmol). The reaction mixture was stirred at 60C overnight. After cooling to r.t., the mixture was filtered and concentrated under reduced pressure. The residue was purified by chromatography on silica gel to afford compound 15d (32 g, 58%).[00155] This compound was characterized by proton NMR (1HNMR) and mass spectroscopy (MS) in accordance with the procedures described herein. Proton NMR yielded the following results: 1H NMR (DMSO-d6, 400MHz): delta 8.13(s, 1 H), 7.23(d, J = 8.8 Hz, 2H), 6.90(d, J = 8.8 Hz, 2H), 5.29(s, 2H), 4.24 (q, J = 6.8 Hz, 2H), 3.71 (s, 3H); 1.26(t, J = 6.8 Hz, 3H). Mass spectroscopy indicated MS (ESI): m/z 387 (M+H)+.

The synthetic route of Ethyl 4-iodo-1H-pyrazole-5-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; ADDEX PHARMA SA; LIVERTON, Nigel, J.; BOLEA, Christelle; CELANIRE, Sylvain; LUO, Yunfu; WO2012/6760; (2012); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 179692-08-1, These common heterocyclic compound, 179692-08-1, name is Ethyl 4-iodo-1H-pyrazole-5-carboxylate, 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 suspension of Intermediate 74b (2.72 g, 10.2 mmol) in acetonitrile (27 mL) was treated with caesium carbonate (5.0 g, 15.3 mmol) then 2-(2- bromoethoxy)tetrahydro-2H-pyran (1.70 mL, 11.2 mmol) and the mixture was stirred at 60 C for 3.5 h. The mixture was evaporated in vacuo and the residue was partitioned between EtOAc and water. The aqueous layer was then extracted with EtOAc (2 x). The combined organic layers were washed with saturated aqueous sodium bicarbonate solution and brine, dried (Na2S04), filtered and evaporated in vacuo. The residue was purified by FCC, using 0-50% EtOAc in cyclohexane, isolating the lower running spot to give the title compound as a colourless glass (1.57 g, 39%). LCMS (Method 3): Rt 3.67 min, m/z 417 [M+Na+].

The synthetic route of 179692-08-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CHIESI FARMACEUTICI S.P.A.; ALCARAZ, Lilian; HURLEY, Christopher; CRIDLAND, Andrew, Peter; JENNINGS, Andrew, Stephen, Robert; WO2014/195402; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

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. 179692-08-1, name is Ethyl 4-iodo-1H-pyrazole-5-carboxylate belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Product Details of 179692-08-1

Intermediate 28 (1-28) Ethyl 2-[ 1 -[(tert-butoxycarbonylamino)methyl]-2-[tert-butyl(dimethyl)silyl]oxy-ethyl]- 4-iodo-pyrazole-3-carboxyla Di-tert-butyl azodicarboxylate (1.97 g, 8.53 mmol) was added to a stirred solution of 4- iodo-lH-pyrazole-3-carboxylic acid ethyl ester (1.26 g, 4.74 mmol), [3-(tert- butyldimethylsilanyloxy)-2-hydroxypropyl]carbamic acid tert- vXy ester (2.90 g, 9.48 mmol) and triphenylphosphine (2.24 g, 8.53 mmol) in THF (23.6 mL) under nitrogen atmosphere. The mixture was stirred at rt for 2.5 h. The solvent was evaporated and the residue was treated with DIPE. The solid (Ph3PO) was filtered off and the filtrate was evaporated in vacuo. The crude product was purified by flash column chromatography (silica; DCM in Heptane 50/50 to 100/0 then EtOAc in DCM 0/100 to 3/97). The desired fractions were collected and concentrated in vacuo to yield intermediate compound 1-28 (2.57 g, 98%) as a colorless oil.

The synthetic route of 179692-08-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; VAN GOOL, Michiel, Luc, Maria; ALONSO-DE DIEGO, Sergio-Alvar; CID-NUNEZ, Jose, Maria; DELGADO-GONZALEZ, Oscar; DECORTE, Annelies, Marie, Antonius; MACDONALD, Gregor, James; MEGENS, Antonius, Adrianus, Hendrikus, Petrus; TRABANCO-SUAREZ, Andres, Avelino; GARCIA-MOLINA, Aranzazu; ANDRES-GIL, Jose, Ignacio; WO2014/195311; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 179692-08-1, name is Ethyl 4-iodo-1H-pyrazole-5-carboxylate, molecular formula is C6H7IN2O2, 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. COA of Formula: C6H7IN2O2

At 0C, NaH (902.12 mg, 22.55 mmol, 60%) was added portionwise into a solution of Example 1A (5 g, 18.79 mmol) in DMF (30 mL) and stirred for 30 min. A solution of dibromodifluoromethane (9.00 g, 42.89 mmol) in DMF (30 mL) was added and stirred at 20C for 16 h. The reaction solution was quenched with water (100 mL) and extracted with ethyl acetate (50 mL * 3). The combined organic phase was washed with brine (100 mL), dried over anhydrous sodium sulfate, filtered and evaporated to give a residue. The residue was purified by column chromatography to give the title compound as a brown liquid (2 g, 26.95%). 1H NMR (400 MHz, CHLOROFORM-d) delta=8.00 (s, 1H), 4.48 (q, J=7.3 Hz, 2H), 1.45 (t, J=7.2 Hz, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 179692-08-1, its application will become more common.

Reference:
Patent; Chai Tai Tianqing Pharmaceutical Group Co., Ltd.; Medshine Discovery Inc.; LIU, Shilan; WANG, Dahai; LIANG, Guibai; HU, Guoping; LI, Jian; CHEN, Shuhui; (167 pag.)EP3418282; (2018); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

179692-08-1, name is Ethyl 4-iodo-1H-pyrazole-5-carboxylate, belongs to pyrazoles-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Product Details of 179692-08-1

Example 15, Step C [00154] To a solution of compound 15c (38 g, 143 mmol) in acetonitrile (380 mL) at r.t. was added K2C03 (39.5 g, 286 mmol) and then PMBCI (24 mL, 177 mmol). The reaction mixture was stirred at 60C overnight. After cooling to r.t., the mixture was filtered and concentrated under reduced pressure. The residue was purified by chromatography on silica gel to afford compound 15d (32 g, 58%).[00155] This compound was characterized by proton NMR (1HNMR) and mass spectroscopy (MS) in accordance with the procedures described herein. Proton NMR yielded the following results: 1H NMR (DMSO-d6, 400MHz): delta 8.13(s, 1 H), 7.23(d, J = 8.8 Hz, 2H), 6.90(d, J = 8.8 Hz, 2H), 5.29(s, 2H), 4.24 (q, J = 6.8 Hz, 2H), 3.71 (s, 3H); 1.26(t, J = 6.8 Hz, 3H). Mass spectroscopy indicated MS (ESI): m/z 387 (M+H)+.

The synthetic route of 179692-08-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; ADDEX PHARMA SA; LIVERTON, Nigel, J.; BOLEA, Christelle; CELANIRE, Sylvain; LUO, Yunfu; WO2012/6760; (2012); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

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 179692-08-1 as follows. name: Ethyl 4-iodo-1H-pyrazole-5-carboxylate

General procedure: Aryl Halide, tetrakis (triphenylphosphine)palladium or Palladium (II)bis(triphenylphosphine) dichloride (0.05eq) and boronic acid or pinnacol ester (1.2eq) were weighed out into a microwave vessel or sealed tube. Acetonitrile (3mL/mmol) and a 1M aqueous solution of Sodium Carbonate (3eq) were added. The vessel was capped and heated thermally 3-18hrs at 100C. Upon completion, the reaction was cooled and crude product was either triterated via addition of water and collection by filtration or extracted with sat ammonium chloride and DCM. If the crude product was an intermediate, it was taken into the next step in most cases w/o further purification or alternatively submitted for reverse phase HPLC purification when it was a final product.Similar to the procedure as described in General Procedure M, ethyl 4-iodo-lH- pyrazole-3-carboxylate was reacted with 1 -ethyl- lH-pyrazol-4-ylboronic acid to give the title compound (343 mg, 27%) as a yellow oil. LC-MS (ES, m/z): 235 [M+H]+.

According to the analysis of related databases, 179692-08-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; BLAQUIERE, Nicole; CASTANEDO, Georgette; FENG, Jianwen A.; CRAWFORD, James John; LEE, Wendy; LIN, Xingyu; HU, Baihua; WU, Guosheng; (218 pag.)WO2016/135163; (2016); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics