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[ CAS No. 741717-63-5 ]

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2D
Chemical Structure| 741717-63-5
Chemical Structure| 741717-63-5
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Product Details of [ 741717-63-5 ]

CAS No. :741717-63-5MDL No. :MFCD10568308
Formula : C13H11F3N2O2 Boiling Point : 304.8°C at 760 mmHg
Linear Structure Formula :-InChI Key :RNOJREZLCGQMPX-UHFFFAOYSA-N
M.W :284.23Pubchem ID :11448972
Synonyms :

Computed Properties of [ 741717-63-5 ]

TPSA : 44.1 H-Bond Acceptor Count : 6
XLogP3 : 3 H-Bond Donor Count : 0
SP3 : 0.23 Rotatable Bond Count : 4

Safety of [ 741717-63-5 ]

Signal Word:WarningClassN/A
Precautionary Statements:P261-P305+P351+P338UN#:N/A
Hazard Statements:H315-H319-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 741717-63-5 ]

  • Upstream synthesis route of [ 741717-63-5 ]
  • Downstream synthetic route of [ 741717-63-5 ]

[ 741717-63-5 ] Synthesis Path-Upstream   1~6

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YieldReaction ConditionsOperation in experiment
85% With trans-N,N'-dimethyl-1,2-cyclohexanediamine; copper(l) iodide; potassium carbonate In toluene at 110℃; for 24.00 h; A mixture of 3-trifluoromethyl-lH-pyrazole-4-carboxylic acid ethyl ester (2.5 g, 12.0 mmol), copper (I) iodide (0.69 g, 3.6 mmol) and potassium carbonate (3.49 g, 25.3 mmol) in toluene (12 mL) in a round bottom flask was purged with argon. To the reaction mixture was then added iodobenzene (1.61 mL, 14.4 mmol) and racemic trans- N,N'-dimethyl-cyclohexane-l,2-diamine (1.16 mL, 7.2 mmol). The slurry was heated under Ar in an oil bath at HO0C for 24 hours. After cooling to room temperature, the reaction mixture was diluted with ethyl acetate and filtered over a bed of celite. The organic washings were combined and concentrated to give a crude which was purified by silica gel chromatography (Isco 120 g column, 0 -> 30percent ethyl acetate/hexanes) to give 1- phenyl-3-trifluoromethyl-lH-pyrazole-4-carboxylic acid ethyl ester (2.91 g, 85percent) as an off-white solid. The NMR spectrum obtained on the sample is compatible with its structure.
85% With potassium carbonate In toluene at 110℃; for 24.00 h; Inert atmosphere Part I:
Preparation of Preferred Intermediates
Preparation of 1-phenyl-3-trifluoromethyl-1H-pyrazole-4-carboxylic acid
A mixture of 3-trifluoromethyl-1H-pyrazole-4-carboxylic acid ethyl ester (2.5 g, 12.0 mmol), copper (I) iodide (0.69 g, 3.6 mmol) and potassium carbonate (3.49 g, 25.3 mmol) in toluene (12 mL) in a round bottom flask was purged with argon.
To the reaction mixture was then added iodobenzene (1.61 mL, 14.4 mmol) and racemic trans-N,N'-dimethyl-cyclohexane-1,2-diamine (1.16 mL, 7.2 mmol).
The slurry was heated under Ar in an oil bath at 110° C. for 24 hours.
After cooling to room temperature, the reaction mixture was diluted with ethyl acetate and filtered over a bed of celite.
The organic washings were combined and concentrated to give a crude which was purified by silica gel chromatography (Isco 120 g column, 0-->30percent ethyl acetate/hexanes) to give 1-phenyl-3-trifluoromethyl-1H-pyrazole-4-carboxylic acid ethyl ester (2.91 g, 85percent) as an off-white solid.
The NMR spectrum obtained on the sample is compatible with its structure.
A mixture of 1-phenyl-3-trifluoromethyl-1H-pyrazole-4-carboxylic acid ethyl ester (1.25 g, 4.4 mmol) and 1N aqueous sodium hydroxide solution (17.3 mL) in methanol (20 mL) was stirred at room temperature overnight.
The reaction mixture was concentrated and acidified to pH~1 with 1N aqueous hydrochloric acid.
The slurry was extracted with methylene chloride and the combined organic layers were washed with saturated sodium chloride and dried over sodium sulfate.
Filtration and concentration gave 1-phenyl-3-trifluoromethyl-1H-pyrazole-4-carboxylic acid (1 g, 89percent yield) as an off-white solid, which was directly used in the next step without further purification. LCMS calcd for C11H7F3N2O2 (m/e) 256, obsd 255 (M-H).
77% With potassium carbonate In toluene at 110℃; for 24.00 h; Sealed tube 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, 77percent) as a solid: 1H NMR (400 MHz, CDCl3) δ 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).
77% With potassium carbonate In toluene at 110℃; for 24.00 h; sealed tube 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, 77percent) as a solid: 1H NMR (400 MHz, CDCl3) δ 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).

Reference: [1] Patent: WO2008/141976, 2008, A1. Location in patent: Page/Page column 55
[2] Patent: US2010/152445, 2010, A1. Location in patent: Page/Page column 8
[3] Journal of Organic Chemistry, 2004, vol. 69, # 17, p. 5578 - 5587
[4] Patent: WO2008/11130, 2008, A2. Location in patent: Page/Page column 134-135
[5] Patent: WO2008/11131, 2008, A2. Location in patent: Page/Page column 270-271
[6] Patent: WO2006/13939, 2006, A1. Location in patent: Page/Page column 47-48
[7] Patent: US2007/123504, 2007, A1. Location in patent: Page/Page column 29
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Reference: [1] Molecules, 2012, vol. 17, # 12, p. 14205 - 14218
[2] Bioorganic and Medicinal Chemistry, 2010, vol. 18, # 7, p. 2785 - 2795
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Reference: [1] Patent: WO2015/97658, 2015, A1. Location in patent: Page/Page column 19; 20
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Reference: [1] Molecules, 2012, vol. 17, # 12, p. 14205 - 14218
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Reference: [1] Molecules, 2012, vol. 17, # 12, p. 14205 - 14218
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Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 12, p. 2527 - 2531
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