Extended knowledge of 54605-72-0

The synthetic route of 1-Phenylpyrazole-4-carboxaldehyde has been constantly updated, and we look forward to future research findings.

These common heterocyclic compound, 54605-72-0, name is 1-Phenylpyrazole-4-carboxaldehyde, 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. Computed Properties of C10H8N2O

A mixture of 1-phenylpyrazole-4-carbaldehyde (18.5 mg, 0.11 mmol), paracyclophanyl piperazine (31.4 mg, 0.11 mmol) and sodium triacetoxyborohydride (27.5 mg, 0.13 mmol) in dichloromethane (1.5 mL) was stirred at room temperature for 24 h. Then, the mixture was added to a saturated aqueous solution of NaHCO3 and extracted with dichloromethane. The organic layer was dried (Na2SO4) and evaporated and the residue was purified by flash chromatography (petroleum ether/ethyl acetate 4:6) to give pure 4 (35.2 mg, 72%) as a colorless solid (mp 78 C). EI-MS: m/z 448 (M+); 1H NMR: (CDCl3, 360 MHz) delta (ppm): 2.60-2.81 (m, 5H), 2.85-3.12 (m, 9H), 3.25 (ddd, J = 12.3 Hz, 9.0 Hz, 6.0 Hz, 1H), 3.37 (ddd, J = 12.7 Hz, 9.7 Hz, 2.4 Hz, 1H), 3.60 (s, 2H), 5.71 (d, J = 1.8 Hz, 1H), 6.27 (dd, J = 7.8 Hz, 1.8 Hz, 1H), 6.35 (dd, J = 7.9 Hz, 1.9 Hz, 1H), 6.40 (d, J = 7.8 Hz, 1H), 6.44 (dd, J = 7.9 Hz, 1.9 Hz, 1H), 6.52 (dd, J = 7.9 Hz, 1.9 Hz, 1H), 6.69 (dd, J = 7.9 Hz, 1.9 Hz, 1H), 7.24-7.31 (m, 1H), 7.41-7.48 (m, 2H), 7.67-7.73 (m, 3H), 7.92 (s, 1H); IR: (KBr) nu (cm-1): 1596. Anal. Calcd for C30H32N4: C, 80.32; H, 7.19; N, 12.49. Found: C, 80.63; H, 7.13; N, 12.32.

The synthetic route of 1-Phenylpyrazole-4-carboxaldehyde has been constantly updated, and we look forward to future research findings.

Reference:
Article; Sanna, Fabrizio; Ortner, Birgit; Huebner, Harald; Loeber, Stefan; Tschammer, Nuska; Gmeiner, Peter; Bioorganic and Medicinal Chemistry; vol. 21; 7; (2013); p. 1680 – 1684;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Brief introduction of 54605-72-0

The synthetic route of 54605-72-0 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. 54605-72-0, name is 1-Phenylpyrazole-4-carboxaldehyde, A new synthetic method of this compound is introduced below., Recommanded Product: 1-Phenylpyrazole-4-carboxaldehyde

General procedure: To a well stirred mixture of 2,6-difluoro-3-aminobenzamide(10) (0.17 g, 1.0 mmol) and 3-n-butoxybenzaldehyde (0.17 g,1.0 mmol) in MeOH (10 mL) at 0 C, was added p-toluenesulfonicacid monohydrate (0.02 g, 0.11 mmol) and the reaction mixturewasstirred for 2 h. After that, excess sodium cyanoborohydride (0.63 g,10.0 mmol)was added in portions to the reaction mixture. After theaddition, the reaction mixture was stirred for further 12 h. The reactionwas quenched by pouring into a separating funnel containing50 mL water and extracted with ethyl acetate (20 mL x 3). Thecombined organic layers were dried over MgSO4, filtered andevaporated under reduced pressure to a crude product, which wassubjected to purification by flash column chromatography on silicagel with gradient elution (20%e50% ethyl acetate in hexane) toafford the titled compound (0.15 g) in 45% yield.

The synthetic route of 54605-72-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Lui, Hok Kiu; Gao, Wei; Cheung, Kwan Choi; Jin, Wen Bin; Sun, Ning; Kan, Jason W.Y.; Wong, Iris L.K.; Chiou, Jiachi; Lin, Dachuan; Chan, Edward W.C.; Leung, Yun-Chung; Chan, Tak Hang; Chen, Sheng; Chan, Kin-Fai; Wong, Kwok-Yin; European Journal of Medicinal Chemistry; vol. 163; (2019); p. 95 – 115;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Brief introduction of 1-Phenylpyrazole-4-carboxaldehyde

The chemical industry reduces the impact on the environment during synthesis 1-Phenylpyrazole-4-carboxaldehyde. I believe this compound will play a more active role in future production and life.

Reference of 54605-72-0, 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. 54605-72-0, name is 1-Phenylpyrazole-4-carboxaldehyde, This compound has unique chemical properties. The synthetic route is as follows.

Example 78 This example illustrates the preparation of 7-Methoxy-2,2-dimethyl-benzo[1,3]dioxole-5-carboxylic acid ((S)-1-cyclobutyl-pyrrolidin-2-ylmethyl)-(1-phenyl-1H-pyrazol-3-ylmethyl)-amide. Experimental conditions analogous to Example 1, from 0.16 g (0.81 mmol) of (S)-2-aminomethyl-pyrrolidine-1-carboxylic acid tert-butyl ester, 70 mg (0.41 mmol) of 1-phenyl-1H-pyrazole-4-carbaldehyde, 4 mL dichloromethane, and 0.17 g (0.81 mmol) of sodium triacetoxyborohydride. (1-Phenyl-1H-pyrazol-3-ylmethyl)-pyrrolidin-2-ylmethyl-amine was treated with 566 muL (4.06 mmol) of triethylamine and 0.43 g (1.79 mmol) of 7-methoxy-2,2-dimethyl-benzo[1,3]dioxole-5-carbonyl chloride. The compound was deprotected using 3 mL of 10% TFA in dichloromethane. 7-Methoxy-2,2-dimethyl-benzo[1,3]-dioxolo-5-carboxylic acid (1-cyclobutyl-pyrrolidin-2-ylmethyl)-[1-(1-ethylidene-penta-2,4-dienyl)-1H-pyrazol-3-ylmethyl]-amide was alkylated using 98 mg (1.22 mmol) cyclobutanone and 0.25 g (1.22 mmol) of sodium triacetoxyborohydride. The compound was purified using reverse phase HPLC, mobile phase with a gradient 20-80% acetonitrile in 50 min, gave 50 mg of white solid as the trifluoroacetate. LC-MSD, m/z for C30H36N4O4 [M+H]+: 517.7. 1H NMR (400 MHz, CDCl3): delta 1.7-2.4 (m, 17H), 2.9-3.1 (m, 1H), 3.6-3.8 (m, 2H), 3.9 (s, 3H), 3.9-4.0 (m, 2H), 4.6-4.8 (m, 2H), 6.6 (s, 1H), 6.7 (s, 1H), 7.3-7.4 (m, 1H), 7.4-7.5 (m, 2H), 7.5 (bs, 1H), 7.6-7.8 (m, 4H), 8.0 (s, 1H), 11.1 (bs, 1H).

The chemical industry reduces the impact on the environment during synthesis 1-Phenylpyrazole-4-carboxaldehyde. I believe this compound will play a more active role in future production and life.

Some scientific research about 1-Phenylpyrazole-4-carboxaldehyde

The chemical industry reduces the impact on the environment during synthesis 1-Phenylpyrazole-4-carboxaldehyde. I believe this compound will play a more active role in future production and life.

Electric Literature of 54605-72-0, 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. 54605-72-0, name is 1-Phenylpyrazole-4-carboxaldehyde, This compound has unique chemical properties. The synthetic route is as follows.

Step 2: A solution of 4-(Piperazin-1 -yl)quinazoline (1.0 g, 4.7 mmol) and 1 -phenyl-1 H-pyrazole- 4-carbaldehyde (0.81 g, 4.7 mmol) in 1 ,2- dichloroethane (20 ml.) was treated with sodium triacetoxy borohydride (1.5 g, 7 mmol) and the reaction mixture was stirred overnight. The mixture was diluted with dichloromethane (30 ml.) and washed sequentially with 25 ml. portions of 1 M NaOH, water and brine. The organic layer was evaporated and the desired product was purified by column chromatography on silica gel column using ethyl acetate/hexane (10-50%) as the mobile phase the desired product was obtained as a white solid (1.5 g). Mass Spec, M+H = 371.

The chemical industry reduces the impact on the environment during synthesis 1-Phenylpyrazole-4-carboxaldehyde. I believe this compound will play a more active role in future production and life.

Extracurricular laboratory: Synthetic route of 54605-72-0

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-Phenylpyrazole-4-carboxaldehyde, other downstream synthetic routes, hurry up and to see.

Related Products of 54605-72-0, The chemical industry reduces the impact on the environment during synthesis 54605-72-0, name is 1-Phenylpyrazole-4-carboxaldehyde, I believe this compound will play a more active role in future production and life.

A solution of 1-phenyl-1H-pyrazole-4-carbaldehyde (5.0 g, 29.0 mmol), (R)-2-methyl-2-propanesulfinamide (3.51 g, 29.0 mmol) and Ti(OiPr)4 (47.7 g, 50 mL, 0.168 mol) in THF (50 mL) was stirred with heating on a water bath at 50 C for 20 h. The resulting mixture was poured into water (250 mL) with stirring for 15 min, then filtered, and the precipitate was washed twice with DCM. The filtrate was diluted with water (200 mL) and extracted with DCM (50 mL * 3). The combined extracts were dried over K2CO3, filtered through the pad of silica gel and evaporated under reduced pressure, and crystallized from iPr2O/n-hexane to afford pure 2d 6.78 g (85%). Rf: 0.5 (EtOAc/n-hexane, 1:1) = -98.7 (c 1, CHCl3). Mp 67.5-68.5 C (iPr2O/n-hexane). 1H NMR (400 MHz, CDCl3): delta 8.58 (s, 1H, CH=N), 8.34 (s, 1H, CHpyr), 8.13 (s, 1H, CHpyr), 7.72 (d, J = 7.9 Hz, 2H, Ph), 7.51-7.47 (m, 2H, Ph), 7.38-7.34 (m, 1H, Ph), 1.26 (s, 9H, tBu) ppm. 13C NMR (100 MHz, CDCl3): delta 154.21, 141.15, 139.33, 129.63 2C, 128.62, 127.59, 121.38, 119.56 2C, 57.56, 22.51 3C ppm. MS (70 eV, EI): m/z (%) = 276 (27) [MH]+, 220 (14), 219 (91), 218 (11), 172 (21), 171 (100), 170 (24), 145 (12), 144 (52), 77 (11). C14H17N3OS (275.4): calcd C 61.06, H 6.22, N 15.26, S 11.64; found C 60.93, H 6.19, N 15.25, S 11.64.

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-Phenylpyrazole-4-carboxaldehyde, other downstream synthetic routes, hurry up and to see.

Analyzing the synthesis route of 54605-72-0

The chemical industry reduces the impact on the environment during synthesis 54605-72-0. I believe this compound will play a more active role in future production and life.

The chemical industry reduces the impact on the environment during synthesis 54605-72-0, name is 1-Phenylpyrazole-4-carboxaldehyde, I believe this compound will play a more active role in future production and life. 54605-72-0

General procedure: An oven-dried 3-neck round-bottomed ask equipped with amagnetic stir bar was charged with aryl aldehyde (1.0 equiv.) andtriphenylphosphine (1.2 or 1.5 equiv.). The system was sealed withthree PFTE septa, and subsequently evacuated and backlled withN2 three times. Dry NMP was added via syringe transfer (PTFE sy-ringe with oven-dried stainless-steel needle), and the system wasimmersed in a preheated 100C oil bath. Once no solid reagentsremained (approximately 2 min of heating), potassium bromodi-uoroacetate (1.5 or 1.8 equiv.) was added portionwise over 0.5 h,with the rate of addition controlling the evolution of CO2 gas. Onceall of the potassium bromodiuoroacetate was added, the solutionwas allowed to stir for 0.5e1 h. Upon completion, the reaction wascooled to room temperature and then quenched with H2O. Subse-quently, Et2O was added to the reaction, and the mixture waswashed with H2O (ve times), and the aqueous layer was back-extracted with Et2O (two times). The combined organic layerswere dried over Na2SO4 and concentrated. The crude material wasdry-packed onto silica gel and then eluted through a plug of silicagel with EtOAc:hexanes (1:1) to remove triphenylphosphine oxide.Subsequently, H2O2 (30% in H2O) was added to the mother liquorand allowed to react for 30 min to oxidize the residual triphenyl-phosphine. The organic layer was washed with H2O (three times),dried over Na2SO4, concentrated, and subjected to normal phaseash chromatography using EtOAc and hexanes.

The chemical industry reduces the impact on the environment during synthesis 54605-72-0. I believe this compound will play a more active role in future production and life.