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[ CAS No. 240800-45-7 ] {[proInfo.proName]}

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Chemical Structure| 240800-45-7
Chemical Structure| 240800-45-7
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CAS No. :240800-45-7 MDL No. :MFCD00236281
Formula : C8H3F4N Boiling Point : -
Linear Structure Formula :- InChI Key :SQAZPEKSXOYPDX-UHFFFAOYSA-N
M.W : 189.11 Pubchem ID :2737551
Synonyms :

Safety of [ 240800-45-7 ]

Signal Word:Danger Class:6.1
Precautionary Statements:P261-P301+P310-P305+P351+P338-P311 UN#:3439
Hazard Statements:H301+H331-H315-H319-H335 Packing Group:Ⅲ
GHS Pictogram:

Application In Synthesis of [ 240800-45-7 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 240800-45-7 ]

[ 240800-45-7 ] Synthesis Path-Downstream   1~14

  • 1
  • [ 240800-45-7 ]
  • [ 354814-19-0 ]
YieldReaction ConditionsOperation in experiment
61.0% With ammonium hydroxide; In 1,4-dioxane; at 120.0℃; under 7600.51 Torr; mixture of 63 (15.0 g, 79.4 mmol, 1.0 eq) in NH4OH (150 mL) and 1,4-dioxane (40 mL) was heated to 120 C in a Parr bomb under 10 atm overnight. The reaction mixture was extracted with DCM (100 mL x 3). The combined organic extracts were washed with brine, dried over Na2SO4, filtered, and concentrated. The residue was purified by SGC (eluting with Petroleum ether / ethyl acetate, 4 / 1) to give the desired product 64 (9.00 g,48.4 mmols, 61.0%) as a white solid.[00453] LCMS: ESI-MS: m/z: 187.1 [M+H1 RT = 1.46 mm. (Method A)
52% With ammonia; In 1,4-dioxane; water; at 120.0℃; under 10343.2 Torr; for 18.0h; Preparation of intermediate 39; <n="40"/>Intermediate 36; 5-amino-2-(trifluoromethyl)benzonitrile; A solution of 5-fluoro-2-(trifluoromethyI)benzonitrile (7.Og, 37.0 mmol, 1 equiv) and 1 ,4-dioxane (10 mL) in ammonia hydroxide (100 mL) 1 ,4-dioxane (10 mL) was heated to 120 0C in Parr bomb under 200 psi for 18 h. The reaction mixture was concentrated down and the residue partitioned between dichloromethane and water. The organics were dried over Na2SO4, filtered and concentrated and the residue purified by silica gel flash column chromatography (0 → 40% ethyl acetate : hexanes) to give intermediate 36 (3.5 g, 52% yield) as a white solid. 1H NMR (400 MHz, DMSOd6) δ ppm 7.49 (d, J=8.79 Hz, 1 H), 7.02 (d, J=2.20 Hz, 1 H), 6.77 - 6.91 (m, 1 H), 6.32 (s, 2 H). ES-LCMS: m/z 187.2 (M+H).
With ammonium hydroxide; In 1,4-dioxane; at 130.0℃; under 10343.2 Torr; for 20.0h; Intermediate 37: 5-Amino-2-(trifluoromethyl)benzonitrile; Ammonium hydroxide solution (50 mL) was added to a stirred solution of 5-fluoro-2- (trifluoromethyl)benzonitrile (commercially available, for example from Alfa Aesar, Ward Hill, MA, USA, 2.0 g, 10.6 mmol) in 1 ,4-dioxane (10 mL) and the reaction mixture was heated to 130C for 20 h under 200 psi pressure in a steel bomb. The reaction mixture was evaporated to dryness, and the residue was diluted with DCM and washed with water. The organic layer was dried over anhydrous Na2S04 and concentrated under reduced pressure to afford the crude product. This was purified by column chromatography (100-200 mesh silica gel), eluting with 20%-40%EtOAc/petroleum ether, to give the title compound (1.2 g).MS ES+ve m/z 185 (M-H).1H NMR (400 MHz, Chloroform-d) δ ppm 4.02-4.30 (br s, 2 H), 6.85 (dd, 1 H), 7.00 (d, 1 H), 7.50 (d, 1 H).
  • 2
  • [ 240800-45-7 ]
  • [ 1354947-86-6 ]
  • 3
  • [ 240800-45-7 ]
  • [ 1354947-88-8 ]
  • 4
  • [ 240800-45-7 ]
  • [ 1354947-90-2 ]
  • 5
  • [ 240800-45-7 ]
  • [ 1354947-92-4 ]
  • 6
  • [ 240800-45-7 ]
  • [ 269409-70-3 ]
  • [ 1367127-42-1 ]
YieldReaction ConditionsOperation in experiment
With caesium carbonate; In N,N-dimethyl-formamide; at 100.0℃; Compound 5d: A mixture of compound 6 (2.1 g, 10.9 mmol), compound 7 (2.4g, 10.9 mmol) and Cs2C03 (3.5 g, 10.9 mmol) in DMF (14 mL) was heated at 100C for 4 hours. After cooling to room temperature, the mixture was filtered through a plug of silica gel and the plug was washed with EtOAc (50 mL). The filtrate was concentrated and the residue was purified by column chromatography (40 g silica gel, 0-30% EtOAc/Hexane) to obtain compound 5d (2.3 g, 6.9 mmol). 1H NMR (400MHz, CD3OD): 7.81 (d, 2H, J=8.8Hz), 7.63 (d, 1H, J=8.8Hz), 7.26 (d, 1H, J=2.4Hz), 7.17 (dd, 1H, Jl=2.4, J2=8.8Hz), 6.98 (d, 2H, J=8.8Hz), 1.28 (s, 12H).
2.3 g With caesium carbonate; In N,N-dimethyl-formamide; at 100.0℃; for 4.0h; [0323] (c) Compound 12 was prepared as follows:[0324] A mixture of compound 16 (2.1 g, 10.9 mmol), compound 17 (2.4g, 10.9 mmol) and Cs2C03 (3.5 g, 10.9 mmol) in DMF (14 mL) was heated at 100C for 4 hours. After cooling to room temperature, the mixture was filtered through a plug of silica gel and the plug was washed with EtOAc (50 mL). The filtrate was concentrated and the residue was purified by column chromatography (40 g silica gel, 0-30% EtOAc/Hexane) to obtain compound 12 (2.3 g, 6.9 mmol). ? NMR (400MHz, CD3OD): ? 7.81 (d, 2H, J=8.8Hz), 7.63 (d, 1H, J=8.8Hz), 7.26 (d, 1H, J=2.4Hz), 7.17 (dd, 1H, Jl=2.4, J2=8.8Hz), 6.98 (d, 2H, J=8.8Hz), 1.28 (s, 12H).
  • 7
  • [ 240800-45-7 ]
  • [ 269409-70-3 ]
  • [ 1433051-89-8 ]
  • 8
  • [ 240800-45-7 ]
  • [ 71597-85-8 ]
  • [ 1437035-07-8 ]
YieldReaction ConditionsOperation in experiment
45% With potassium carbonate; In water; N,N-dimethyl-formamide; at 100.0℃; for 3.0h; A mixture of 3-cyano-4-trifluoromethyl- l -fluorobenzene (70 g, 0.37 mol, Oakwood), 4-hydroxyphenylboronic acid (50 g, 0.36 mol, Boron Molecular), K2C03 (70 g) and DMF/water (400 mL/40 mL) was heated to 100C for 3h. After cooling to RT, the mixture was diluted with water (1 L) and extracted with EtOAc (1.5 L). The organic layer was washed with water (0.5 L) and brine, concentrated and purified by chromatographed over silica gel with 4% MeOH in chloroform to give (4-(3-cyano-4-(trifluoromethyl)phenoxy)phenyl)boronic acid as pink solid (50 g, 45%).
42% With caesium carbonate; In N,N-dimethyl-formamide; at 100.0℃; for 4.0h; A mixture of compound 27 (2.1 g, 10.9 mmol), compound 28 (2.4 g), and Cs2C03 (3.5 g, 10.9 mmol) in DMF (14 mL) was heated at 100C for 4 hours. After cooling to room temperature, the mixture was diluted with water (l OOmL) and extracted with EtOAc (3x100 mL). The combined organic layer was washed with brine, concentrated and purified by column chromatography (silica gel,EtOAc/hexanes 1/1 ) to give (4-(3-cyano-4-trifluoromethyl)phenoxy)phenyl)boronic acid (29) (pink solid, 42%). ? NMR (400MHz, CD3OD): 7.59 - 7.86 (3H, m), 7.31 - 7.37 ( 1 H, m), 7.19 - 7.26 (1 H, m), 6.9 - 7.10 (2H, m).
  • 9
  • [ 240800-45-7 ]
  • [ 71597-85-8 ]
  • [ 1454918-08-1 ]
  • 10
  • [ 106-41-2 ]
  • [ 240800-45-7 ]
  • 5-(4-bromophenoxy)-2-(trifluoromethyl)benzonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% With potassium carbonate; In acetonitrile; at 80.0℃; for 14.0h;Inert atmosphere; (a) The starting compound 5-(4-bromophenoxy)-2-(trifluoromethyl)benzonitrile (30b) was prepared as shown below: Accordingly, a mixture of compound 40 (1.0 eq, Aldrich), compound 41 (2 g, 0.9 eq, Matrix Scientific) and K2CO3 (2 eq) in 25 mL of CH3CN was heated at 80 C. under argon for 14 hours. After cooling to room temperature, water (30 mL) was added, extracted with EtOAc (2*100 mL), concentrated and purified by column (silica gel, Hexanes, then Hexanes/EtOAc 10/1) to give compound 30b as a white solid (2.8 g, 81%). 1H-NMR (400 MHz, CDCl3) δ: 7.75 (d, 1H, 8.8 Hz), 7.57-7.61 (m, 2H), 7.36-7.37 (m, 1H), 6.97-7.01 (m, 2H), 7.08-7.11 (m, 2H).
  • 11
  • [ 240800-45-7 ]
  • 5-{4-[3-(1,2-dihydroxyethyl)-1H-indol-1-yl]phenoxy}-2-(trifluoromethyl)-benzonitrile [ No CAS ]
  • 12
  • [ 240800-45-7 ]
  • C26H17F3N2O4 [ No CAS ]
  • 13
  • [ 240800-45-7 ]
  • 2-(1-(4-(3-cyano-4-(trifluoromethyl)phenoxy)phenyl)-1H-indol-3-yl)-2-oxoacetamide [ No CAS ]
  • 14
  • [ 240800-45-7 ]
  • 2-(1-(4-(3-cyano-4-(trifluoromethyl)phenoxy)phenyl)-1H-indol-3-yl)-2-hydroxyacetamide [ No CAS ]
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