Category: 2644-93-1

Electric Literature of 2644-93-1, 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. 2644-93-1, name is 1,3,5-Trimethyl-1H-pyrazole-4-carbaldehyde belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

n-BuLi (2.1 mL, 2.5 M in hexanes, 5.2 mmol) was added drop-wise to a -50 C. solution consisting of 3-(benzyloxy)-6-bromo-4-chloro-2-methoxyquinoline (2.0 g, 5.3 mmol, Intermediate 29: step d) and THF (50 mL). The resultant reaction mixture was stirred at -50 C. for 20 minutes and then treated with a solution of 1,3,5-trimethyl-1H-pyrazole-4-carbaldehyde (730 mg, 5.28 mmol) and THF (15 mL) at -50 C. The resulting mixture was stirred at room temperature for 20 minutes before quenching with saturated aqueous NH4Cl (20 mL) and extracting with dichloromethane:methanol (5:1, 50 mL*10). The combined organic extracts were dried over Na2SO4, filtered and concentrated to dryness under reduced pressure to give the crude product, which was purified by FCC (silica gel, eluent: petroleum ether:ethyl acetate=5:1 to 1:1) to afford the title compound.

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, 1,3,5-Trimethyl-1H-pyrazole-4-carbaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; JOHNSON & JOHNSON; LEONARD, KRISTI A.; BARBAY, KENT; EDWARDS, JAMES P.; KREUTTER, KEVIN D.; KUMMER, DAVID A.; MAHAROOF, UMAR; NISHIMURA, RACHEL; URBANSKI, MAUD; VENKATESAN, HARIHARAN; WANG, AIHUA; WOLIN, RONALD L.; WOODS, CRAIG R.; FOURIE, ANNE; XUE, XIAOHUA; CUMMINGS, MAXWELL D.; MCCLURE, KELLY; TANIS, VIRGINIA; US2015/111870; (2015); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 2644-93-1,Some common heterocyclic compound, 2644-93-1, name is 1,3,5-Trimethyl-1H-pyrazole-4-carbaldehyde, molecular formula is C7H10N2O, 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: Sodium triacetoxyborohydride (46.3 mg, 0.218 mmol) was added toa mixture of 10c (65 mg, 0.146 mmol) and tetrahydropyran-4-carbaldehyde(18.3 mg, 0.160 mmol) in 1,2-dichloroethane (1.30 mL). The mixture was stirred at room temperature for 2 h, sat.NaHCO3 aqueoussolution was added, and the mixture was extracted with CHCl3. The organic layer was washed with brine, dried with Na2SO4, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (CHCl3/MeOH) to give the desired compound as a white solid (41.0 mg, 52%). 1H NMR (DMSO-d6) delta1.00-1.29 (3H, m), 1.44-1.60 (3H, m), 1.64-1.85 (3H, m), 1.95-2.17(5H, m), 2.62-2.71 (1H, m), 2.78-2.88 (1H, m), 3.08 (3H, s), 3.15-3.29(2H, m), 3.70-3.83 (2H, m), 4.01 (3H, s), 4.05 (3H, s), 4.27-4.37 (2H,m), 7.26 (1H, s), 8.11 (1H, s), 8.43 (1H, d, J=2.3 Hz), 8.85 (1H, d,J=2.3 Hz), 9.37 (1H, s); ESI-MS m/z 545.3 [(M+H)+]; HRMS(ESI) m/z calcd for C26H37N6O5S [(M+H)+]: 545.2541, found: 545.2537

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,3,5-Trimethyl-1H-pyrazole-4-carbaldehyde, its application will become more common.

Reference:
Article; Hamajima, Toshihiro; Takahashi, Fumie; Kato, Koji; Sugano, Yukihito; Yamaki, Susumu; Moritomo, Ayako; Kubo, Satoshi; Nakamura, Koji; Yamagami, Kaoru; Hamakawa, Nozomu; Yokoo, Koji; Fukahori, Hidehiko; Bioorganic and Medicinal Chemistry; vol. 26; 14; (2018); p. 3917 – 3924;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

These common heterocyclic compound, 2644-93-1, name is 1,3,5-Trimethyl-1H-pyrazole-4-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. category: pyrazoles-derivatives

To a flask containing 6-bromo-4-chloro-2-methoxy-3-(4-(trifluoromethyl)benzyl)quinoline (1.37 g, 3.86 mmol, Intermediate 10: step d) was added THF (45 mL) at room temperature which resulted in a colorless homogeneous mixture. The solution was cooled to -78 C. and then n-BuLi (2.5 M in hexanes, 1.8 mL, 4.5 mmol) was added dropwise. The color of the solution became a reddish-brown color. After 4 minutes, 1,3,5-trimethyl-1H-pyrazole-4-carbaldehyde (300 mg, 2.17 mmol, in 3 mL THF) was introduced and the color of the mixture changed from reddish-brown to a yellow-greenish color over 5 minutes. The mixture was allowed to warm to 0 C. over 45 minutes at which time the reaction was quenched with aqueous NH4Cl solution. The mixture was diluted further with water and extracted with EtOAc (3*150 mL). The combined organics were washed with brine, dried over MgSO4, filtered and concentrated to give a light orange foam. FCC on silica gel (2% MeOH-DCM increasing to 8% MeOH-DCM) afforded the title compound as a light yellow amorphous solid. 1H NMR (500 MHz, CDCl3) delta ppm 8.23 (s, 1H), 7.78 (d, J=8.6 Hz, 1H), 7.56-7.47 (m, 3H), 7.40 (d, J=8.1 Hz, 2H), 6.01 (d, J=3.0 Hz, 1H), 4.35 (s, 2H), 4.06 (s, 3H), 3.70 (s, 3H), 2.14 (s, 3H), 2.12 (s, 3H), 2.09 (d, J=3.3 Hz, 1H). MS (ESI): mass calcd. for C25H23ClF3N3O2, 489.1; m/z found, 490.1 [M+H]+.

The synthetic route of 1,3,5-Trimethyl-1H-pyrazole-4-carbaldehyde has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; LEONARD, KRISTI A.; BARBAY, KENT; EDWARDS, JAMES P.; KREUTTER, KEVIN D.; KUMMER, DAVID A.; MAHAROOF, UMAR; NISHIMURA, RACHEL; URBANSKI, MAUD; VENKATESAN, HARIHARAN; WANG, AIHUA; WOLIN, RONALD L.; WOODS, CRAIG R.; FOURIE, ANNE; XUE, XIAOHUA; CUMMINGS, MAXWELL D.; US2015/105372; (2015); 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. 2644-93-1, name is 1,3,5-Trimethyl-1H-pyrazole-4-carbaldehyde belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. SDS of cas: 2644-93-1

(n-BuLi (1.02 mL, 2.5 M in hexane, 2.55 mmol) was added drop-wise to a -70 C. solution consisting of 3-(benzyloxy)-6-bromo-4-chloro-2-methoxy-8-methylquinoline (1.0 g, 2.5 mmol, Intermediate 89: step f) and THF (50 mL). The resultant reaction mixture was stirred at -70 C. for 20 minutes and then treated with a solution of 1,3,5-trimethyl-1H-pyrazole-4-carbaldehyde (352 mg, 2.55 mmol) and THF (15 mL) at -70 C. The resulting mixture was stirred at room temperature for 20 minutes before quenching with saturated aqueous NH4Cl (20 mL) and extracting with dichloromethane:methanol (5:1, 50 mL*10). The combined organic extracts were dried over Na2SO4, filtered and concentrated to dryness under reduced pressure to give the crude product, which was purified by FCC (silica gel, eluent: petroleum ether:ethyl acetate=5:1 to 1:1) to afford the title compound.

The synthetic route of 2644-93-1 has been constantly updated, and we look forward to future research findings.

Reference of 2644-93-1, These common heterocyclic compound, 2644-93-1, name is 1,3,5-Trimethyl-1H-pyrazole-4-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.

At room temperature for 6-bromo-4-chloro-2-methoxy-3 – (4 – (trifluoromethyl) benzyl) quinoline (1.37 g, 3.86 mmol, Intermediate 10: step d) comprises that the flask, THF It was added (45 mL) to obtain a colorless, homogeneous mixture.Cooling the solution to -78 Next,ndropwise -BuLi (2.5 M, 1.8 mL, 4.5 mmol in hexane).The color of the solution was reddish brown.4 minutes after, 1,3,5-trimethyl -1H-pyrazole-4-carbaldehyde (300 mg, 2.17 mmol, 3 mL of THF) was introduced to he a mixture of red-brown color over 5 min It was in turn greenish yellow.The mixture was warmed to 0 over 45 minutes and, at this time the reaction NH4was quenched with aqueous solution of Cl.The mixture was diluted further with water and extracted with EtOAc (3 ¡Á 150 mL).The combined organics were washed with brine, MgSO4dried, filtered, and concentrated to give a light orange foam.Silica gel by FCC on (2% MeOH-DCM, increased to 8% MeOH-DCM), to give the title compound as a pale yellow non-crystalline solid.

The synthetic route of 2644-93-1 has been constantly updated, and we look forward to future research findings.

Reference of 2644-93-1, These common heterocyclic compound, 2644-93-1, name is 1,3,5-Trimethyl-1H-pyrazole-4-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.

At room temperature for 6-bromo-4-chloro-2-methoxy-3 – (4 – (trifluoromethyl) benzyl) quinoline (1.37 g, 3.86 mmol, Intermediate 10: step d) comprises that the flask, THF It was added (45 mL) to obtain a colorless, homogeneous mixture.Cooling the solution to -78 Next,ndropwise -BuLi (2.5 M, 1.8 mL, 4.5 mmol in hexane).The color of the solution was reddish brown.4 minutes after, 1,3,5-trimethyl -1H-pyrazole-4-carbaldehyde (300 mg, 2.17 mmol, 3 mL of THF) was introduced to he a mixture of red-brown color over 5 min It was in turn greenish yellow.The mixture was warmed to 0 over 45 minutes and, at this time the reaction NH4was quenched with aqueous solution of Cl.The mixture was diluted further with water and extracted with EtOAc (3 ¡Á 150 mL).The combined organics were washed with brine, MgSO4dried, filtered, and concentrated to give a light orange foam.Silica gel by FCC on (2% MeOH-DCM, increased to 8% MeOH-DCM), to give the title compound as a pale yellow non-crystalline solid.

The synthetic route of 2644-93-1 has been constantly updated, and we look forward to future research findings.

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. 2644-93-1, name is 1,3,5-Trimethyl-1H-pyrazole-4-carbaldehyde, A new synthetic method of this compound is introduced below., category: pyrazoles-derivatives

Sodium triacetoxyborohydride (17.5 mg, 0.082 mmol) was added to a solution of piperidin-4-yl-benzothiazole (15 mg, 0.069 mmol, Compound 2h, Step 2) and 1,3,5- trimethyl-1H-pyrazole-4-carbaldehyde (9.5 mg, 0.069 mmol, Bionet) in DCE (340 .iL) at room temperature. After three hours, the reaction was purified directly by flash chromatography (4g silica, 0-10% MeOH/DCM). The title compound was obtained as a yellow solid (15 mg, 65% yield). LCMS (ESI) m/z 341.4 (M+1) retention time 3.2 mm. ?H NMR (300MHz, CD3OD) oe = 7.97-7.89 (m, 2H), 7.52-7.37 (m, 2H), 3.71 (s, 3H), 3.63 (s, 2H), 3.28-3.17 (m, 3H), 2.53 (dt,J=2.3, 11.7 Hz, 2H), 2.28 (s, 3H), 2.24 (m, 2H), 2.22 (s, 3H), 2.09-1.97 (m, 2H).

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.