Month: April 2021

These common heterocyclic compound, 1145-01-3, name is 3,5-Diphenyl-1H-pyrazole, 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. COA of Formula: C15H12N2

To a flame dried flask was added 3,5-diphenylpyrazole (0.21 g, 0.95 mmol), Selectfluor (0.76 g, 2.1 mmol), and dried, ground molecular sieves (3 A) (0.5 g) followed by dry acetonitrile (distilled from CaH2 and stored over molecular sieves) (3 mL) and the mixture was heated at 80 C (oil bath temp) under N2 for 40 min. The dark yellow solution was then diluted with EtOAc and filtered. The filtrate was evaporated onto silica gel and subjected to flash chromatography on silica gel using 10:1 hexanes/EtOAc as eluent to give first difluoropyrazole 2 (0.19 g, 74% yield) and then the hydrated difluoropyrazole 3 (0.054 g, 20% yield) as yellow solids. The products were recrystallized from hexanes (2) or cyclohexane (3) to give analytical samples as pale yellow crystals. Data for 4,4-difluoro-3,5-diphenyl-4H-pyrazole (2): mp 91.2-91.8 C. IR (ATR): 3071, 3054, 1594, 1582, 1556, 1497, 1447, 1379, 1353, 1339, 1220, 1101, 1021, 872, 777, 720, 698, 681 cm-1. 1H NMR (300 MHz, DMSO-d6): 8.05 (d, J = 7.5 Hz, 4H), 7.74-7.64 (m, 6H). 13C NMR (75 MHz, DMSO-d6): 161.8 (t, J = 22.7 Hz), 133.8 (s), 129.9 (s), 127.8 (s), 125.7 (t, J = 265.9 Hz), 124.7 (s). 19F NMR (282 MHz, DMSO-d6): -116.4 (s). Anal. calcd for C15H10F2N2: C, 70.30; H, 3.93; N, 10.93; found: C, 70.41; H, 4.02; N, 10.82. Data for 4,4-difluoro-3,5-diphenyl-4,5-dihydro-1H-pyrazol-5-ol (3): mp 105.6-106.3 C. IR (ATR): 3354, 3238 (broad), 1593, 1571, 1491, 1332, 1449, 1238, 1136, 1068, 1050, 1016, 964, 889, 778, 688, 656, 635 cm-1. 1H NMR (300 MHz, DMSO-d6): 8.77 (s, 1H), 7.69 (d, J = 7.2 Hz, 2H), 7.59-7.56 (m, 2H), 7.48-7.40 (m, 6H), 7.31 (s, 1H). 13C NMR (75 MHz, acetone-d6): 143.9 (dd, J = 22.5 Hz, 24.0 Hz), 136.8 (d, J = 2.3 Hz), 134.2 (s), 130.1 (s), 129.8 (s), 129.6 (s), 128.9 (s), 128.2 (d, J = 1.6 Hz), 126.2 (d, J = 1.6 Hz), 125.3 (dd, J = 251.7 Hz, 261.9 Hz), 92.9 (dd, J = 20.8 Hz, 32.4 Hz). 19F NMR (282 MHz, DMSO-d6): -103.4 (d, J = 259 Hz), -122.7 (d, J = 259 Hz). Anal. calcd for C15H12F2N2O: C, 65.68; H, 4.41; N, 10.21; found: C, 65.58; H, 4.39; N, 10.23.

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

Reference of 26621-44-3, A common heterocyclic compound, 26621-44-3, name is 3-Nitro-1H-pyrazole, molecular formula is C3H3N3O2, 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.

To a mixture of 3-nitro-1H-pyrazole (5 g, 44.22 mmol, 1 eq) in DMF (50 mL) was added NaH (2.12 g, 53.06 mmol, 60 wt.% in mineral oil, 1.2 eq) at 0 C. The reaction mixture was stirred at 0 C for 0.5 hour. Then 2,2-dimethyloxirane (3.51 g, 48.64 mmol, 1.1 eq) was added into the above mixture at 0 C. The resulting mixture was warmed to 25 C and stirred at 25 C for 1 hour. The reaction mixture was quenched by addition of H2O (100 mL) and extracted with EtOAc (2 x 50 mL). The combined organic layers were washed with brine (2 x 30 mL), dried over Na2SO4, filtered and concentrated under reduced pressure to give the title compound (3.7 g, crude) as yellow oil, which was used directly in the next step.1H NMR (400 MHz, CDCl3): d 7.60 (dd, 1 H), 6.93 (d, 1 H), 4.21 (s, 2 H) and 1.27 (s, 6 H). One exchangable proton not observed.LCMS: m/z 208.1 (M+Na)+(ES+)

The synthetic route of 26621-44-3 has been constantly updated, and we look forward to future research findings.

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. 51985-95-6, name is Methyl 5-hydroxy-1-methyl-1H-pyrazole-3-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 51985-95-6

c) l-Methyl-5-(5-methyl-3-pyridin-2-yl-isoxazol-4-ylmethoxy)-lH-pyrazole-3-carboxylic acid methyl esterTo a stirred solution of 5 -hydroxy- 1 -methyl- lH-pyrazole-3-carboxylic acid methyl ester (400 mg, 2.6 mmol) and (5-methyl-3-pyridin-2-yl-isoxazol-4-yl)-methanol (500 mg, 2.6 mmol) inTHF(10 mL) at 5 0C under argon was added triphenylphosphine (862 mg, 3.3 mmol), then diethyl azodicarboxylate (573 mg, 3.3 mmol) was added dropwise. The reaction mixture was warmed to room temperature and stirred overnight. The reaction mixture was then evaporated. Purification by chromatography (silica, dichloromethane: methanol = 9:1) then purification using a 5 x 50 cm Chiralpak AD column at room temperature using an isopropanol:heptane (2:8) mobile phase with UV detection at 220 nM afforded the title compound (400 mg, 48percent) as a white solid. MS: m/e = 328.3 [M+H]+.

According to the analysis of related databases, 51985-95-6, the application of this compound in the production field has become more and more popular.

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. 943541-20-6, name is 3-Chloro-6-(1-methyl-1H-pyrazol-4-yl)pyridazine, A new synthetic method of this compound is introduced below., SDS of cas: 943541-20-6

A mixture of 3-chloro-6-(1-methyl-1H-pyrazol-4-yl)pyridazine (494 mg, 2.5 mmol) in AcOH (20 mL) was stirred at 120 C for 4 h. The reaction mixture was concentrated under reduced pressure, and water was added to the concentrates. The generated solids was filtered and dried to afford 6-(1-methyl-1H-pyrazol-4-yl)pyridazin-3(2H)-one (431 mg, 98 %). 6-(1-Methyl-1H-pyrazol-4-yl)pyridazin-3(2H)-one (2a) 1HNMR (300 MHz, CDCl3) delta 8.70 (d, J = 11.3 Hz, 1H), 7.96(s, 1H), 6.94 (s, 1H), 6.62 (d, J = 11.3 Hz, 1H), 3.95 (s, 3H).

The synthetic route of 943541-20-6 has been constantly updated, and we look forward to future research findings.

Related Products of 37687-18-6, A common heterocyclic compound, 37687-18-6, name is 1-(1-Methyl-1h-pyrazol-4-yl)-ethanone, molecular formula is C6H8N2O, 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.

Intermediate 282-Bromo- 1 -( 1 -methyl- 1 H-pyrazol-4-vDethanoneIn a 25 mL flask, 1 -(I -methyl- lH-pyrazol-4-yl)ethanone (0.602 g, 4.85 mmol) was dissolved in chloroform (20 mL). The colorless solution was made acidic with the addition of a few drops of HBr in acetic acid (3.92 mg, 0.05 mmol). A chloroform solution containing Br2 (0.262 mL, 5.09 mmol) was added dropwise via an addition funnel. The reaction mixture was stirred at room temperature for 1 h, and then concentrated under reduced pressure. The crude solid was triturated in ethyl acetate, filtered, and dried in vacuo. The free base was obtained by triturating the product in 5% NaHCCb for 2 h. The solid was collected by filtration, washed with water, isopropyl alcohol and then dried in vacuo. Isolation gave 874 mg of the title compound.LC/MS (ES+)[(M+H)+]: 204 for C6H7BrN2O.1H NMR (300 MHz, d6-DMSO): 3.88 (s, 3H), 4.56 (s, 2H), 7.99 (s, IH), 8.47 (s, IH).

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.

Application of 2075-46-9,Some common heterocyclic compound, 2075-46-9, name is 4-Nitro-1H-pyrazole, molecular formula is C3H3N3O2, 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.

Intermediate 5: 1 H-Pyrazol-4-amine. 4-Nitro-1H-pyrazole (Manchester organics; 1.13 g, 9.99 mmol) was dissolved in ethanol (50 ml). This solution was added carefully to 10% palladium on carbon (Aldrich; 102 mg) under a nitrogen atmosphere. The atmosphere was exchanged to hydrogen, and the mixture was stirred vigorously at room temperature under a hydrogen atmosphere. After 45 min, ca. 700 ml of hydrogen had been taken up, and no further hydrogen was taken up over the next 30 min. Stirring was stopped and the atmosphere was exchanged to nitrogen. The solution was filtered through cellite (10 g cartridge) and washed with further ethanol (150 ml). Relevant fractions (as verified by TLC) were combined and concentrated in vacuo to give a red oil. Trituration with DCM gave the title compound (815 mg) as a red solid; 1 H NMR (MeOH-d4, 400 MHz) delta (ppm) 7.20 (2 H, s).

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

Synthetic Route of 2033-45-6, 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. 2033-45-6 name is 3,5-Dimethyl-4-iodopyrazole, 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.

(b) 4-iodo–3,5-dimethyl- I -tosyl- 1 H-pyrazole: Triethylamine (1 2.73g, 126. 8nunol) was added toa solution of 4-iodo-3,5-dimeihyl-1H-pyrazole (141)7g. 63.4nimol) in DCM (250 mL), followed byaddition of TsC1 (13.3g 69,7minoi). The mixture was then stirred overnight. After completionof the reaction, water (100 mL) was added and the mixture was extracted with EtOAc (3x80m1). The orgamie solvent was collected and removed under reduced pressure, the residue was purified by silica gel-column to obtaine 4-iodo-3,5-dhnethyl-1-tosyl-IH-pyrazoie (8.0g. yield 33.6%) as a white solid ,LCMS (022): 222.7 [M+H]t Rt :1.65 mm

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3,5-Dimethyl-4-iodopyrazole, and friends who are interested can also refer to it.

Electric Literature of 5932-27-4, 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. 5932-27-4, name is Ethyl 1H-pyrazole-3-carboxylate, This compound has unique chemical properties. The synthetic route is as follows.

EXAMPLE 19; The fluoro bromopyridine (1 eq, Ig), pyrazole (4 eq, 5.023 g), ligand (0.2 eq, 0.196 g), Cu2O (0.05 eq, 51 mg) and Cs2CO3 (2 eq, 4.65 g) were mixed in CH3CN (8 mL) and heated to 82 0C in a sealed vessel for 16 h under N2. The solution was diluted with DCM and filtered through Celite, partitioned with water, and then brine. The product was evaporated in vacuo, and purified by column chromatography (SiO2) with 10 to 20percent EtOAc/hexanes to obtain the major regioisomeric product as a white solid. Then LiBELi (2 eq, 128 mg) was added to this ester intermediate (1 eq, 690 mg) in THF (30 mL) and heated to reflux for 15 h. Then 0.1 N HCl (a few drops) was added and stirred for 1 h, followed by a DCM/H2O partition, and the aqueous layer was basified with NaOH to pH = 9 and extracted with DCM. The combined organic phase was dried to obtain the alcohol as a white solid. Iodine (1.52 eq, l.O58g) in AcOEt (25 ml) was added to an AcOEt (25 mL ) solution of this alcohol (1 eq, 530 mg), followed by Ph3P (1.52 eq, 1.094 g) and imidazole (1.52eq, 0.284 g) over 10 min at RT. The solution was stirred for 1 h and washed with Na2S2O3 and brine. The product was dried in vacuo, and the solid residue was extracted with Hexanes 3 x 70 ml and filtered. The filtration was dried to obtain the iodide product as a white solid. Then KOtBu ( 1.5 eq, 250 mg) was added to N-(diphenylmethylene)- glycine ethyl ester (1.5 eq, 595 mg) in THF at RT and stirred for 10 min. To this solution was added the iodide intermediate (1 eq, 450 mg) in THF (5 mL) at -78 0C, and the mixture was slowly warmed to RT over 2 h. An additional 1 eq of KOtBu was added to the solution at RT and stirred for 50 h at RT. The mixture was quenched with NH4Cl and extracted with DCM, washed with H2O and then brine, and dried in vacuo. The residue was purified by column chromatography (hex/AcOEt – 20percent) to obtain the product. This intermediate (1 eq. 200 mg) was dissolved in saturated 7 N NH3/MeOH (7 mL) solution and heated to 60 0C for 24 h in a sealed tube. The reaction mixture was dried in vacuo and, the residue was dissolved in 5 ml THF and 1 N HCl (2 mL) at RT and heated to 60 0C for 20 min. The THF was removed in vacuo. The aqueous layer was washed with Et2O, dried in vacuo to obtain the amino carboxamide as a white solid HCl-salt. The amide intermediate (1 eq, 68 mg), triflate (1.2 eq, 82 mg), Pd2(DBA)3 (0.1 eq. ), Xantphos (0.2 eq, ) and Cs2CO3 (2.4 eq, 186 mg) were combined in dioxane (2 mL) under N2 and heated to 75 0C for 13 h. The mixture was cooled and diluted with CH2C12 (2 mL), filtered through Celite, and the CH2CI2 removed in vacuo, and Et2psi was added to the filtrate and extracted with 3 N HCl (3 x 10 mL). The combined aqueous layer was basified with Na2CO3 to pH== 9 at 0 0C and extracted with AcOEt (3 xlO mL). The combined organic layer was dried in vacuo to obtain the crude product as a light yellow oil. Lastly, LiOH (0.5 M, 3 mL) was added to this ester in THF/MeOH at 0 0C and stirred for 20 h. Then AcOH was added to acidify to pH= 7 at 0 0C and HPLC purification provided the product. 1HNMR, CD3OD delta 8.48 (d, IH), 8.30 (d, IH), 7.99(dd, IH), 7.74 (m, IH), 6.43(d, IH), 4.37 (t, IH), 3.50(d, 2H), 2.88 (m, 2H), 2.29 (br, 2H), 1.62 (m, 4H); LCMS m/z 374 (M+H).

The chemical industry reduces the impact on the environment during synthesis Ethyl 1H-pyrazole-3-carboxylate. I believe this compound will play a more active role in future production and life.

These common heterocyclic compound, 175277-11-9, name is 3-tert-Butyl-1-methylpyrazole-5-carboxylic Acid, 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

EXAMPLE 7 N-{5-[(2-aminopyrimidin-5-yl)ethynyl]pyridin-3-yl}-3-tert-butyl-1-methyl-1H-pyrazole-5-carboxamide DIPEA (387 mg) was added to a mixture of 5-[(5-aminopyridin-3-yl)ethynyl]pyrimidin-2-amine (Intermediate 11) (211 mg), 3-tert-butyl-1-methyl-1H-pyrazole-5-carboxylic acid (364 mg) and HBTU (642 mg) in DMF (3 mL) and stirred for 65 hours at ambient temperature. The mixture was added dropwise to stirred 1M aqueous sodium hydroxide (100 mL). The solid formed was filtered off, and purified by RPHPLC to give the title compound (121 mg, 32%); 1H NMR (DMSO-d6) 1.28 (s, 9H), 4.02 (s, 3H), 6.97 (s, 1H), 7.19 (s, 2H) 8.32 (t, 1H), 8.42 (d, 1H), 8.47 (s, 2H), 8.79 (d, 1H) 10.39 (br s, 1H); MS m/e MH+376.

The synthetic route of 3-tert-Butyl-1-methylpyrazole-5-carboxylic Acid 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. 217073-76-2, name is 1-(4-Fluorophenyl)-5-methyl-1H-pyrazole-4-carboxylic acid, A new synthetic method of this compound is introduced below., Safety of 1-(4-Fluorophenyl)-5-methyl-1H-pyrazole-4-carboxylic acid

To a suspension of 6-(2-amino-5-chlorothiazol-4-yl)-3,4-dihydroquinolin-2(1-H)-one (0.100 g, 0.41 mmol), 1-(4-fluorophenyl)-5-methyl-1H-pyrazole-4-carboxylic acid (0.0.99 g, 0.45 mmol), pyridine (0.15 mL, 1.83 mmol) in acetonitrile (4 mL) in a sealed tube was added propylphosphonic anhydride solution (50 wt % in ethyl acetate, 0.61 mL, 1.02 mmol). The sealed tube was heated to 100 C. for 16 h. After cooling, the precipitate was collected by filtration and washed with cold 1:1 acetonitrile/water to give 1-(4-fluorophenyl)-5-methyl-N-(4-(2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)thiazol-2-yl)-1H-pyrazole-4-carboxamide (0.111 g, 61%). 1H NMR (400 MHz, DMSO-d): delta 12.43 (bs, 1H), 10.19 (s, 1H), 8.58 (s, 1H), 7.74 (m, 1H), 7.69 (dd, 1H, J=8.4, 2.0 Hz), 7.63 (m, 2H), 7.48 (s, 1H), 7.44 (m, 2H), 6.90 (d, 1H, J=8.0 Hz), 2.93 (t, 2H, J=7.2 Hz), 2.57 (s, 3H), 2.50 (partial masked under d-DMSO, in, 2H); MS (ESI): Calcd. For C23H18FN5O2S: 447 found 448 (M+1)+.

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.