Category: 155377-19-8

155377-19-8, name is Ethyl 3-(trifluoromethyl)pyrazole-4-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. Application In Synthesis of Ethyl 3-(trifluoromethyl)pyrazole-4-carboxylate

To lambda/-(5-(chloromethyl)-2,3-dihydro-7/-/-inden-1-yl)propane-2-sulfonamide (0.250 mmol, 72 mg) in DMF (4 ml.) was added ethyl 3-(trifluoromethyl)-7/-/-pyrazole-4-carboxylate (0.250 mmol, 52.1 mg) and Potassium carbonate (0.750 mmol, 104 mg). The resultant solution was heated to 60 0C with stirring. After 1.5 h the reaction mixture was concentrated to remove DMF before partitioning between EtOAc/H2O and the phases mixed and separated. The organic layer was washed with water (x 4) and brine before drying and concentration to a yellow oil. Purification on 10g Si eluting with 1% MeOH/DCM gave the desired compound as an off-white solid (60 mg, 0.131 mmol, 52.2 %). 1H NMR (400 MHz, CDCI3) delta 1.33 (t, 3H) 1.44 (d, 6H) 1.95 (m, 1 H) 2.65 (m, 1 H) 2.85 (m, 1 H) 3.00 (m, 1 H) 3.25 (m, 1 H) 4.15 (d, 1 H) 4.29 (q, 2H) 4.95 (m, 1 H) 5.30 (s, 2H) 7.14 (s, 1 H) 7.18 (d, 1 H) 7.48 (d, 1 H) 7.88 (s, 1 H).

The synthetic route of 155377-19-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; N.V. ORGANON; WO2009/147167; (2009); 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. 155377-19-8, name is Ethyl 3-(trifluoromethyl)pyrazole-4-carboxylate, A new synthetic method of this compound is introduced below., HPLC of Formula: C7H7F3N2O2

Ethyl 3-(trifluoromethyl)-1H-pyrazole-4-carboxylate (95.00 g, 0.456 mol) was dissolved in dry THF (1 L) and the resulting solution cooled in an acetone/ice bath. A 1M solution of LiAlH4 in THF (550 mL, 0.550 mol) was added over 30 min, keeping the temperature <10 C. Cooling was then removed and the reaction mixture was stirred at RT for 4 h. The reaction was again cooled and a 1:1 THF:water solution (250 mL) was added with cooling (maintaining the temperature <20 C.), followed by 5M HCl (160 mL) to neutrality/pH 6. EtOAc (1.5 L) was added and the mixture stirred for 30 min then left to settle overnight. The resulting grey granular solid was removed by filtration through dicalite and washed with EtOAc. The combined filtrates were washed with brine and dried over MgSO4, before concentrating in vacuo to give a white solid (76.00 g, 0.457 mol, 100%).1H NMR (400 MHz, CD3OD): delta 4.61 (s, 2H), 7.75 (s, 1H). 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. Reference:
Patent; N.V. Organon; US2009/131455; (2009); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 155377-19-8, These common heterocyclic compound, 155377-19-8, name is Ethyl 3-(trifluoromethyl)pyrazole-4-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.

Example 118: Preparation of l-allyl-S-trifluoromethyl-lH-pyrazole^-carboxylic acid ethyl ester and 2-allyl-3-trifluoromethyl-2Hl-pyrazole-4-carboxylic acid ethyl ester3-Trifluoromethyl-lH-pyrazole-4-carboxylic acid ethyl ester (500 mg, 2.4 mmol) was dissolved in acetone and stirred. To the solution was added potassium carbonate(498 mg, 3.6 mmol), in one portion, followed by dropwise addition of allyl bromide (0.31 ml, 3.6 mmol). The reaction mixture was stirred at room temperature for 5 hours. The reaction mixture was poured into water and extracted twice with ethyl acetate. The combined organic extracts were dried over magnesium sulfate and concentrated to give a 9:1 mixture of l-allyl-3-trifluoromethyl-l//-pyrazole-4-carboxylic acid ethyl ester (isomer A) and 2-allyl-3-trifluoromethyl-2H-pyrazole-4-carboxylic acid ethyl ester (isomer B) (557 mg, 93% yield) as a yellow solid. Isomer A (major isomer) 1H-NMR (400 MHz, CDCl3): 1.39 (t, 3H, Me), 4.35 (q, 2H, CH2), 4.8 (d, 2H, CH2), 5.3-5.45 (dd, 2H, CH2), 6.05 (m, IH, CH), 8.01 (s, IH, CH) ppm. Isomer B (minor isomer) 1H-NMR (400 MHz, CDCl3): 1.39 (t, 3H, Me), 4.35 (q, 2H, CH2), 4.95 (d, 2H, CH2), 5.1-5.3 (dd, 2H, CH2), 6.05 (m, IH, CH), 7.98 (s, IH, CH) ppm.

Statistics shows that Ethyl 3-(trifluoromethyl)pyrazole-4-carboxylate is playing an increasingly important role. we look forward to future research findings about 155377-19-8.

Reference:
Patent; SYNGENTA LIMITED; WO2007/71900; (2007); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 155377-19-8, A common heterocyclic compound, 155377-19-8, name is Ethyl 3-(trifluoromethyl)pyrazole-4-carboxylate, molecular formula is C7H7F3N2O2, 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.

According to the procedure of Buchwald et al . (J. Org. Chem. 2004, 69, 5578), to a 50 mL sealed tube flushed with argon were added copper (I) iodide (0.02288 g, 0.1201 mmol) , K2CO3 (0.6972 g, 5.045 mmol), and ethyl 3- (trifluoromethyl) -IH- pyrazole-4-carboxylate (0.500 g, 2.402 mmol). ( IS, 2S) -N1,N2- Dimethylcyclohexane-1, 2-diamine (0.06834 g, 0.4805 mmol) and 2-bromophenol (0.3343 mL, 2.883 mmol) were then added along with 3 mL of toluene (degassed under argon) . The tube was sealed and heated to 1100C overnight, then cooled to room temperature and the mixture was filtered through celite to remove the solid. The filtrate was concentrated under vacuum and the residue was purified by chromatography (10% ether/DCM) to give ethyl 1- (2-hydroxyphenyl) -3- (trifluoromethyl) -IH- pyrazole-4-carboxylate (0.660 g, 91%) as a solid: 1H NMR (400 MHz, CDCl3) delta 1-40 (t, 3H, J = 7.0 Hz), 4.39 (q, 2H, J = 7.0 Hz), 7.00 (m, IH), 7.16 (m, IH), 7.31 (m, IH), 7.42 (m, .1H), 8.56 (m, IH).

The synthetic route of 155377-19-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; WO2008/11130; (2008); A2;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 155377-19-8,Some common heterocyclic compound, 155377-19-8, name is Ethyl 3-(trifluoromethyl)pyrazole-4-carboxylate, molecular formula is C7H7F3N2O2, 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 solution of ethyl 3- {trifluoromethyl) -lH-pyrazole-4- carboxylate (0.208 g, 1.0 mmol) in DMF were added lH-indol-5- ylboronic acid (0.322 g, 2.00 mmol), Cu(OAc)2 (0.136 g, 0.75 rninol)/ and pyridine (0.162 ml, 2.00 mmol) and the mixture was stirred at room temperature for 3 days . The mixture was diluted with DCM and filtered through a pad of silica gel. The filtrate was concentrated in vacuo and the residue was purified by silica gel column chromatography (3:1 hexanes/EtOAc) to give ethyl 1- (lH-indol-5-yl) -3- (trifluoromethyl) -lH-pyrazole-4- carboxylate (0.313 g, 97%) as a solid: 1H NMR (CDCl3) delta 1.39 (t, 3H7 J = 7.0 Hz), 4.37 Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; WO2008/11131; (2008); A2;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

These common heterocyclic compound, 155377-19-8, name is Ethyl 3-(trifluoromethyl)pyrazole-4-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. Computed Properties of C7H7F3N2O2

(S)-Benzyl 5-(hydroxymethyl)-2,3-dihydro-7/-/-inden-2-ylcarbamate (2.96 mmol, 880mg) was dissolved in DCM (10 ml.) and thionyl chloride (5.92 mmol, 0.432 ml, 704 mg) added. The mixture was stirred at room temperature for 30 min TLC before the solvent was removed under reduced pressure and residual thionylchloride azeotroped with DCM (x3). To the residue was added potassium carbonate (8.88 mmol, 1227 mg) followed by DMF (8 ml) then ethyl 3-(trifluoromethyl)-7/-/-pyrazole-4-carboxylate (2.96 mmol, 616 mg) and the mixture heated to 60 0C. After 1 h the mixture was concentrated and partitioned between EtOAc/H2O and the organic layer was washed with water (x 3). The organic layer was dried, filtered and concentrated to give a yellow oil which was purified by flash chromatography eluting with 15% EtOAc/Heptane to give the desired isomer as a colourless oil (45 mg, 0.092 mmol, 3.1%). 1H NMR (400 MHz, CDCI3) delta 1.34 (t, 3H) 2.75 (m, 2H) 3.25 (m, 2H) 4.33 (q, 2H), 4.50 (m, 1 H) 4.95 (m, 1 H), 5.08 (s, 2H) 5.48 (s, 2H) 7.00 (m, 2H) 7.15 (d, 1 H) 7.34 (m, 5H) 7.99 (s, 1 H).

The synthetic route of Ethyl 3-(trifluoromethyl)pyrazole-4-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; N.V. ORGANON; WO2009/147167; (2009); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 155377-19-8, These common heterocyclic compound, 155377-19-8, name is Ethyl 3-(trifluoromethyl)pyrazole-4-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.

Example 122: Preparation of l-difluoromethyl-3-trifluoromethyl-l//-pyrazole-4- carboxylic acid ethyl ester and 2-difluoromethyl-3-trifluoromethyl-2/:/-pyrazole-4- carboxylic acid ethyl esterSodium hydride (60% in mineral oil) (320 mg, 7.93 mmol) was washed with hexane (2x 10 ml) and suspended in tetrahydrofiiran (20 ml) in a three necked flask. 3- Trifluoromethyl-l//-pyrazole-4-carboxylic acid ethyl ester (1.5 g, 7.21 mmol) (prepared according to JP 2000/044541) in tetrahydrofiiran (10 ml) was added dropwise and the solution stirred at room temperature for 30 minutes. Chlorodifluoromethane was bubbled through the solution for 5 minutes and then the mixture was stirred at room temperature for 3 hours, with additional chlorodifluoromethane bubbled through the solution after every hour for 5 minutes. The reaction mixture was stored at room temperature for 16 hours. The reaction mixture was quenched by addition of water and extracted with ethyl acetate. The organic extract was washed with water and brine, dried over magnesium sulfate and concentrated. The residue was purified by column chromatography on silica gel (eluent: 0-25% ethyl acetate in hexane) to give l-difluoromethyl-3-trifluoromethyl- l//-pyrazole-4-carboxylic acid (isomer A) (870 mg, 47% yield) and 2-difluoromethyl-3- trifluoromethyl-2H-pyrazole-4-carboxylic a’cid (isomer B) (500 mg, 27% yield). Isomer A 1H-NMR (400 MHz, CDCl3): 1.37 (t, 3H, Me), 4.37 (q, 2H, CH2), 7.37 (t, IH, CH), S.07 (s, IH, CH) ppm. Isomer B 1H-NMR (400 MHz, CDCl3): 1.37 (t, 3H, Me), 4.37 (q, 2H, CH2), 7.22 (t, IH, CH), 8.43 (s, IH, CH) ppm.

Statistics shows that Ethyl 3-(trifluoromethyl)pyrazole-4-carboxylate is playing an increasingly important role. we look forward to future research findings about 155377-19-8.

Synthetic Route of 155377-19-8, These common heterocyclic compound, 155377-19-8, name is Ethyl 3-(trifluoromethyl)pyrazole-4-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.

According to the procedure of Buchwald et al. [J. Org. Chem. 2004, 6″S, 5578), to a 350 mL sealed tube flushed vigorously with nitrogen were added ethyl 3- (trifluoromethyl) – lH-pyrazole-4-carboxylate (20.0 g, 96.1 ramol) , 1-iodobenzene s (12.9 ml, 115 mmol) , potassium carbonate (27.9 g, 202 mmol), copper (I) iodide (0.915 g, 4.80 mmol), and (IS, 2S) -N1,N2- dimethylcyclohexane-l,2-diamine (1.37 g, 9.61 mmol), followed by degassed toluene (100 ml) . The mixture was stirred for 24 hours a.t 1100C7 cooled to room temperature, and filtered through o a short silica pad which was rinsed with toluene and EtOAc thoroughly. The filtrate was concentrated in vacuo to give ethyl l-phenyl-3- (trifluoromethyl) -lH-pyrazole-4-carboxylate(21 g, 77%) as a solid: 1H NMR (400 MHz, CDCl3) delta 1.39 (t, 3H, J = 7.0 Hz), 4.37 (q, 2H, J = 7.0 Hz), 7.42 (m, IH), 7.52 (m, 2H), 5 7.72 (m, 2H), 8.48 (m, IH).

The synthetic route of 155377-19-8 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. 155377-19-8, name is Ethyl 3-(trifluoromethyl)pyrazole-4-carboxylate, A new synthetic method of this compound is introduced below., Formula: C7H7F3N2O2

According to the procedure of Buchwald et al . (J. Oxg. Chem. 2004, 69, 5578), to a 350 iaL sealed tube flushed vigorously with nitrogen was added ethyl 3- (trifluoromethyl) – lH-pyrazole-4-carboxylate (20.0 g, 96.1 mmol) , 1-iodobenzene (12.9 inL, 115 mmol), potassium carbonate (27.9 g, 202 mmol), copper(I) iodide (0.915 g, 4.80 mmol), and (IS, 2S) -N1,N2- dimethylcyclohexane-l,2-diamine (1.37 g, 9.61 mmol), followed by degassed (argon) toluene (100 mL) . The mixture was stirred for 24 hours at 1100C, cooled to room temperature, and filtered through a short silica pad which was thoroughly rinsed with toluene and AcOEt- The filtrate was concentrated in vacuo to give ethyl l-phenyl-3- (trifluoromethyl) -lH-pyrazole-4- carboxylate (21 g, 77%) as a solid: 1H NMR (400 MHz, CDCl3) delta 1.39 (t, 3H, J = 7.0 Hz), 4.37 (q, 2H, J = 7.0 Hz), 7.42 (m, IH), 7.52 (m, 2H), 7.72 (m, 2H), 8.48 (m, 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.

Electric Literature of 155377-19-8, The chemical industry reduces the impact on the environment during synthesis 155377-19-8, name is Ethyl 3-(trifluoromethyl)pyrazole-4-carboxylate, I believe this compound will play a more active role in future production and life.

Ethyl 3-(trifluoromethyl)-1H-pyrazole-4-carboxylate (1.50 g, 7.21 mmol) was dissolved in dry THF (50 mL) and the resulting solution cooled to -78 oC. To the resulting solution was added, 2 M solution of LAH (6.01 mL, 14.41 mmol) in THF over 30 min by keeping the temperature <10 C. The reaction mixture was allowed to come to ambient temperature, stirred for 4 h and was cooled again with to -10 oC. The reaction was quenched with the addition of 1:1 THF:water (50 mL) mixture with cooling (maintaining the temperature <20 C), followed by 5M HCl to neutralise to pH 6. The reaction mixture was diluted with EtOAc (100 mL), stirred for 30 min and left to settle for 1 h. The resulting solid was removed by filtration through Celite and washed with EtOAc. The filtered organic layer was washed with brine, dried over MgSO4 and evaporated under reduced pressure. The crude product was triturated with ether (2 x 25 mL) to obtain Intermediate 89A (0.60 g, 50.10%).1H NMR (400 MHz, DMSO-d6) delta ppm 4.44 (s, 2 H), 5.02 (s, 1 H), 7.83 (s, 1 H), 13.73 (br. s., 1 H). LCMS (Method-H): retention time 0.54 min, [M- H] 165.0. 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, Ethyl 3-(trifluoromethyl)pyrazole-4-carboxylate, other downstream synthetic routes, hurry up and to see.