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Chemical Structure| 16264-67-8 Chemical Structure| 16264-67-8

Structure of 16264-67-8

Chemical Structure| 16264-67-8

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Product Details of [ 16264-67-8 ]

CAS No. :16264-67-8
Formula : C8H3F4N
M.W : 189.11
SMILES Code : FC1=C(F)C(F)=C(F)C2=C1NC=C2
MDL No. :MFCD00236717
InChI Key :DTNBMVQXEVNTLO-UHFFFAOYSA-N
Pubchem ID :140051

Safety of [ 16264-67-8 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319
Precautionary Statements:P264-P280-P302+P352-P305+P351+P338-P332+P313-P337+P313-P362

Application In Synthesis of [ 16264-67-8 ]

* 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 [ 16264-67-8 ]

[ 16264-67-8 ] Synthesis Path-Downstream   1~35

  • 1
  • [ 623-73-4 ]
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  • [ 124614-51-3 ]
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  • 3
  • [ 50-00-0 ]
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  • [ 124-40-3 ]
  • [ 30683-41-1 ]
  • 4
  • [ 16264-67-8 ]
  • [ 33513-42-7 ]
  • [ 30683-38-6 ]
  • 5
  • acetaldehyde pentafluorophenylhydrazone [ No CAS ]
  • [ 16264-67-8 ]
  • 6
  • [ 19282-55-4 ]
  • [ 16264-67-8 ]
YieldReaction ConditionsOperation in experiment
47% With manganese(IV) oxide; In benzene; at 20 - 30℃; for 60h;Molecular sieve; Inert atmosphere; A magnetically stirred mixture of indoline 6 (4.50 g, 23.5 mmol), activated MnO2(22.0 g), type 4A molecular sieves, and 190 ml of dry benzene was stirred for 60 h during which time thetemperature was maintained at 20 oC, occasionally reaching 30 oC. After the mixture was filtered usingFiltercell, the solid residue was placed in a Soxhlet apparatus and extracted with 300 mL of dry benzene for 7h. The filtrate and the extraction liquid were then combined and concentrated in vacuo to yield a brown oil.The oil was then purified by chromatography over neutral alumina (25 g) in hexanes (3 cm column), elutingfirst with hexanes (250 mL), then 50:50 hexane-Et2O (250 mL), and finally, with Et2O (250 mL). The hexane andhexane-ether fractions were concentrated in vacuo to yield 2.1 g (47%) of 7: mp 92-94 oC (lit.26 mp 93-93.5 oC;lit.27 mp 91-92.5 oC). IR (KBr) 3470, 1540, 1480, 1420, 1390, 1350, 980, 880 cm-1; UV (95% EtOH) λmax 227, 250nm; 1H NMR (CDCl3) δ 8.36 (s, broad, 1H), 7.20 (m, 1H), 6.62 (m, 1H).
  • 7
  • [ 653-30-5 ]
  • [ 16264-67-8 ]
  • 1-(2'-Pentafluorophenylethyl)-4,5,6,7-tetrafluoroindole [ No CAS ]
  • 10
  • [ 16264-67-8 ]
  • [ 4330-21-6 ]
  • 1',2'-dideoxy-1'-(N-4,5,6,7-tetrafluoroindole)-3',5'-di-O-p-toluoyl-D-ribofuranose [ No CAS ]
  • 11
  • [ 16264-67-8 ]
  • [ 19099-93-5 ]
  • N-benzyloxycarbonyl-4-(4,5,6,7-tetrafluoroindol-3-yl)piperidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
66% With triethylsilane; trimethylsilyl trifluoromethanesulfonate; In dichloromethane; Step 1 To a solution of N-benzyloxycarbonyl-4-piperidone (20.2 g, 90.6 mmol) in methylene chloride (600 ml) at 0 C. was added trimethylsilyl trifluoromethanesulfonate (35.1 ml, 181.2 mmol) followed by the slow dropwise addition of a solution of <strong>[16264-67-8]4,5,6,7-tetrafluoroindole</strong> (17.1 g, 90.6 mmol) in methylene chloride (300 ml) over 2.5 h. After 1.5 h, triethylsilane (57.9 ml, 362.4 mmol) was added and the reaction was allowed to warm to RT over 30 min. The reaction mixture was quenched with sat. sodium bicarbonate and the separated organic layer was dried over MgSO4 and concentrated in vacuo. The residue was partitioned between 50% acetonitrile/hexanes (1400 ml) and the separated acetonitrile layer was concentrated in vacuo. The solid residue was recrystallized from absolute EtOH to afford N-benzyloxycarbonyl-4-(4,5,6,7-tetrafluoroindol-3-yl)piperidine (66%) as a white solid.
  • 12
  • [ 16264-67-8 ]
  • [ 1001013-72-4 ]
  • 4,5,6,7-tetrafluoro-1-(4-(4-(pyridin-2-yl)-1-(pyridin-3-yl)-1H-imidazol-2-yl)phenyl)-1H-indole [ No CAS ]
YieldReaction ConditionsOperation in experiment
31% With potassium phosphate;copper(l) iodide; trans-1,2-cyclohexanediamine; In 1,4-dioxane; at 150℃; for 1h;Microwave irradiation; Example 38; 4.5.6.7-tetrafluoro-1-f4-(4-(pyridin-2-vl)-1-fpvridin-3-vl)-1H-imidazol-2-vl)pheϖvlV1 H-iϖdole; <n="122"/>A mixture of 2-(2-(4-iodophenyl)-1-(pyridin-3-yl)-1H-imidazol-4-yl)pyridine (200 mg,0.47 mmol), <strong>[16264-67-8]4,5,6,7-tetrafluoroindole</strong> (106 mg, 0.56 mmol), CuI (134 mg, 0.7 mmol), K3PO4(199 mg, 0.94 mmol) and fraϖs-1,2-cyclohexanediamiϖe (6 mg, 0.05 mmol) in p-dioxane (2 mL) was heated by microwave at 150 0C for 1h, filtered, concentrated, and the residue purified by SGC (0.5 and 1% MeOH in DCM, 0.5 % NH4OH). Yield 70 mg, 31%. 1H NMR(CDCI3) .58.68 (dd, 1H, J = 1.5, 4.9 Hz), 8.64 (d, 1H, J = 2 Hz), 8.56 (ddd, 1H, J = 1, 2, 5 Hz),8.13 (dt, 1H1 J = ~1, 8 Hz), 7.93 (s, 1H), 7.77 (dt, 1H, J = 2, 7.9 Hz), 7.65 (ddd, 1H1 J = 1.7,2.5, 8.2 Hz), 7.65 (m, 2H), 7.42 (ddd, 1H1 J = 1, 5, 8 Hz)1 7.37-7.34 (m, 2H), 7.19 (m, 2H),6.76 (dd, 1H, J = 2, 3.3 Hz). MS (AP+) m/e 486 (MH+). IC50 = 170 nM
  • 13
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  • [ 680193-27-5 ]
  • 14
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  • [ 680193-28-6 ]
  • 15
  • [ 16264-67-8 ]
  • Diisopropyl-phosphoramidous acid (2R,3S,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(4,5,6,7-tetrafluoro-indol-1-yl)-tetrahydro-furan-3-yl ester 2-cyano-ethyl ester [ No CAS ]
  • 18
  • [ 16264-67-8 ]
  • [ 28834-98-2 ]
  • 19
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  • [ 34063-68-8 ]
  • 20
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  • [ 88752-74-3 ]
  • 22
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  • [ 31845-30-4 ]
  • 23
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  • [ 30419-39-7 ]
  • 24
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  • [ 124614-50-2 ]
  • 26
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  • [ 124614-49-9 ]
  • 27
  • [ 110-86-1 ]
  • [ 16264-67-8 ]
  • C5H5N*C8H3F4NO3S [ No CAS ]
  • 28
  • [ 16264-67-8 ]
  • [ 24303-61-5 ]
  • [ 895157-63-8 ]
  • 29
  • [ 16264-67-8 ]
  • [ 1255171-72-2 ]
  • [ 1255172-25-8 ]
  • 30
  • [ 16264-67-8 ]
  • [ 202596-67-6 ]
  • [ 1255172-27-0 ]
  • 31
  • [ 50-00-0 ]
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  • [ 210562-49-5 ]
  • [ 1266605-94-0 ]
  • 34
  • [ 1228813-89-5 ]
  • [ 16264-67-8 ]
  • [ 1450916-36-5 ]
  • 35
  • [ 1363411-74-8 ]
  • [ 16264-67-8 ]
  • [ 1450916-36-5 ]
YieldReaction ConditionsOperation in experiment
140 mg; 42 mg With potassium hydroxide; In acetonitrile; for 2h;Reflux; General procedure: To a stirred solution of aniline 4 (1mmol), 2-methyl-3-butyn-2-ol 5b (252mg, 3mmol) in dry MeCN (9mL) were added Pd(PPh3)2Cl2 (28mg, 0.04mmol), CuI (17mg, 0.09mmol) and Et3N (1.5mL) at room temperature under an argon atmosphere. The reaction mixture was stirred at 50C for 1h. Then the mixture was heated up to boiling, and KOH (168mg, 3mmol) was added. The mixture was maintained under reflux with stirring, cooled to room temperature and diluted with CH2Cl2 (5mL). The suspension was placed into a chromatography column filled with silica gel (to minimize volatilization of indoles 2(a-c)c). The column was washed with hexane/ethyl acetate (15:1) and then with hexane/ethyl acetate (5:1) under the TLC control to isolate indoles 2(a-c)c and 2(a-c)b, respectively, after evaporation of solvents in vacuo.
 

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