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Chemical Structure| 115661-37-5 Chemical Structure| 115661-37-5

Structure of 115661-37-5

Chemical Structure| 115661-37-5

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Product Details of [ 115661-37-5 ]

CAS No. :115661-37-5
Formula : C7H5FN2
M.W : 136.13
SMILES Code : NC1=C(C#N)C=CC=C1F
MDL No. :MFCD07368774
InChI Key :UNISSOLHERSZOW-UHFFFAOYSA-N
Pubchem ID :2783392

Safety of [ 115661-37-5 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of [ 115661-37-5 ]

* 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 [ 115661-37-5 ]

[ 115661-37-5 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 115661-37-5 ]
  • [ 425379-16-4 ]
YieldReaction ConditionsOperation in experiment
53% To a solution of 2-amino-3-fluorobenzonitrile (17.07 g, 0.125 mol) in 1,4-dioxane (20 ml) was added 48% aqueous hydrobromic acid (200 ml) and the solution was cooled to 0C before adding dropwise a solution of sodium nitrite (9.95 g, 0.144 mol) in water (22 ml) over 35 min so that the temperature did not rise above 3C. The resulting mixture was stirred at 2-3C for 2 h then poured onto a cooled (5C) solution of copper (I) bromide (26.98 g, 0.188 mol) in 48% hydrobromic acid (100 ml). The mixture was stirred for 10 min then heated to 50C over 1 h. The mixture was cooled to ambient temperature, diluted with water (11) and extracted with diethyl ether (2 x 500 ml). The combined organic extracts were washed with 1 M aqueous Na2SO3 (500 ml), then saturated aqueous NH4C1 (200 ml), dried (MgSO4), and evaporated to give a brown oil/solid. Purification by chromatography (silica gel, 10% EtOAc/isohexane) and trituration of a mixed fraction with isohexane afforded 13.22 g (53%) of 2-bromo-3- fluorobenzonitrile as a pale yellow solid : 1H NMR (360 MHz, CDCl3) 5 7.62-7. 68 (1H, m), 7.74-7. 85 (1H, ddd, J 9, 9,1), 7.74-7. 85 (1H, ddd, J 8, 1, 1).
2-Amino-3-fluorobenzonitrile (9.8 g, 71.9 mmol) was bromo-deaminated as described in Example 1 to afford 2-bromo-3-fluorobenzonitrile as a pale brown solid: 1H NMR (360 MHz, CDCl3) delta 7.62-7.68 (1H, m), 7.74-7.85 (1H, ddd, J 9, 9, 1 Hz), 7.74-7.85 (1H, ddd, J 8, 1, 1 Hz).
  • 2
  • [ 1124-16-9 ]
  • [ 115661-37-5 ]
  • [ 796851-03-1 ]
  • [ 1224888-11-2 ]
YieldReaction ConditionsOperation in experiment
53.4% Step 1 To a degassed solution of 2,5-dichloro-4-iodopyridine (8 g, 29.2 mmol), 2-amino-3-fluorobenzonitrile (3.98 g, 29.2 mmol) and potassium triphosphate (18.60 g, 88 mmol) in 1,4-dioxane (60 ml) stirred under nitrogen at the room temperature was added DPEPhos (1.258 g, 2.337 mmol) and palladium acetate (0.262 g, 1.168 mmol) The reaction mixture was stirred at reflux for 18 hr. The reaction mixture was filtered. 3-Methyl-1-(1-methylethyl)-1H-pyrazol-5-amine (4.07 g, 29.2 mmol) and cesium carbonate (28.6 g, 88 mmol) were added. The reaction mixture was degassed and palladium acetate (0.262 g, 1.168 mmol) and DPEPhos (1.258 g, 2.337 mmol) were added. The reaction mixture was refluxed overnight. The reaction mixture was filtered and the solid was dissolved in water, heated to 50° C. and stirred for 10 minutes, then filtered again. 2-[(5-Chloro-2-[3-methyl-1-(1-methylethyl)-1H-pyrazol-5-yl]amino}-4-pyridinyl)amino]-3-fluorobenzonitrile (6 g, 15.59 mmol, 53.4percent yield) was isolated as an orange solid. 1H NMR (400 MHz, DMSO-d6) d ppm 1.23 (d, J=6.57 Hz, 6H) 2.07 (s, 3H) 4.32 (quin, J=6.57 Hz, 1H) 5.64 (d, J=2.02 Hz, 1H) 5.83 (s, 1H) 7.39-7.58 (m, 1H) 7.63-7.82 (m, 2H) 7.88 (s, 1H) 8.26 (br. s., 1H) 8.41 (br. s., 1H); HPLC Rt=2.35 min, MS (ESI): 385.0 [M+H]+.
 

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