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Chemical Structure| 72159-22-9 Chemical Structure| 72159-22-9

Structure of 72159-22-9

Chemical Structure| 72159-22-9

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Product Details of [ 72159-22-9 ]

CAS No. :72159-22-9
Formula : C11H7N3O2
M.W : 213.19
SMILES Code : O=C1N(C2=CC=NN2)C(C3=C1C=CC=C3)=O
English Name :2-(1H-Pyrazol-5-yl)isoindoline-1,3-dione

Safety of [ 72159-22-9 ]

Application In Synthesis of [ 72159-22-9 ]

* 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 [ 72159-22-9 ]

[ 72159-22-9 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 886496-75-9 ]
  • [ 72159-22-9 ]
  • [ 1253188-39-4 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 2-(1H-pyrazol-3-yl)-1H-isoindole-1,3(2H)-dione With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.0833333h; Inert atmosphere; Stage #2: 1-(bromomethyl)-4-chloro-2-(trifluoromethyl)benzene In N,N-dimethyl-formamide at 20℃; Inert atmosphere; 37 A mixture of 2-(1 H-pyrazol-3-yl)-1 H-isoindole-1 ,3(2/-/)-dione (for a preparation see Intermediate 28)(3 g, 14.1 mmol) and potassium carbonate (2.92 g, 21.1 mmol) in DMF (30 ml) was stirred under nitrogen at ambient temperature for 5 min. To the pale yellow suspension was added 1-(bromomethyl)-4-chloro-2- (trifluoromethyl)benzene (3.85 g, 14.07 mmol, Alfa Aesar). The mixture turned to a colourless suspension. The reaction mixture was stirred at ambient temperature under nitrogen overnight. The reaction mixture was diluted with DCM (50 ml) and water (50 ml). To the emulsion was added brine (30 ml). The resulting phases were separated and the aqueous layer further extracted with DCM (50 ml). The combined organic extracts were filtered through a hydrophobic frit and the solvent removed in vacuo to give 2-(1-[4-chloro-2-(trifluoromethyl)phenyl]methyl}-1 H-pyrazol-3-yl)-1 H- isoindole-1 ,3(2H)-dione (6.14 g) as an off-white gum.
  • 2
  • [ 151412-12-3 ]
  • [ 72159-22-9 ]
  • [ 1251929-63-1 ]
YieldReaction ConditionsOperation in experiment
31% Stage #1: 2-(1H-pyrazol-3-yl)-1H-isoindole-1,3(2H)-dione With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.5h; Stage #2: 2-fluoro-3-methylbenzyl bromide In N,N-dimethyl-formamide at 0 - 80℃; for 47.0333h; 30 Intermediate 30: 2-{1-[(2-fluoro-3-methylphenyl)methyl]-1H-pyrazol-3-yl}-1H-isoindole-1,3(2H)-dione 1.00 g (4.69 mmol) of Intermediate 27 was dissolved in 15 mL of DMF (dry) at 0° C. 0.188 g of NaH (Aldrich, 4.69 mmol) were added to the solution and the mixture was stirred and kept at 0° C. for 30 min. To this mixture of reaction, was added dropwise a solution of 1-(bromomethyl)-2-fluoro-3-methylbenzene (ALFAAESAR, 953 mg, 4.69 mmol) in 5 mL DMF (dry), over a period of 2 min. The mixture was stirred at r.t. for 3 h. 1 eq more of 1-(bromomethyl)-2-fluoro-3-methylbenzene (953 mg, 4.69 mmoll) was added to the reaction and was heated to 80° C. 0.2 eq of NaH c.a. every 2 h until 0.8 eq were added. After 44 hours reaction was partitioned between NH4Cl (aq, sat) and EtOAc. Organic fraction was dried over MgSO4 (anh) and concentrated to dryness to yield 1.64 g of a crude that was purified three times by Si(II) chromatography with gradient Hex/EtOAc. 491 mg (yield: 31%) of 2-{1-[(2-fluoro-3-methylphenyl)methyl]-1H-pyrazol-3-yl}-1H-isoindole-1,3(2H)-dione were obtained as white solid. 1H NMR (300 MHz, DMSO-d6) δ ppm: 7.88-7.96 (m, 5H), 7.23-7.28 (m, 1H), 7.07-7.11 (m, 2H), 6.39 (d, 1H), 5.40 (s, 2H), 2.24 (d, 3H). [ES+MS] m/z 336 (MH+).
 

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