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Chemical Structure| 6576-05-2 Chemical Structure| 6576-05-2

Structure of 6576-05-2

Chemical Structure| 6576-05-2

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Product Details of [ 6576-05-2 ]

CAS No. :6576-05-2
Formula : C13H10FNO
M.W : 215.22
SMILES Code : FC1=CC=C(C(CC2=CC=NC=C2)=O)C=C1
MDL No. :MFCD03069461

Safety of [ 6576-05-2 ]

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

Application In Synthesis of [ 6576-05-2 ]

* 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 [ 6576-05-2 ]

[ 6576-05-2 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 108-89-4 ]
  • [ 116332-54-8 ]
  • [ 6576-05-2 ]
YieldReaction ConditionsOperation in experiment
With lithium diisopropyl amide; In tetrahydrofuran; heptane,THF ethyl benzene; Step 1 1-(4-fluorophenyl)-2-(4-pyridyl)-ethanone To a solution of lithium diisopropyl amide (Aldrich Chemical Co. 2.0 M in heptane,THF ethyl benzene) 3.1 mL (6.3 mmol) in 6 mL of anhydrous THF at -78C under nitrogen was added 0.5 g (5.3 mmol) of 4-picoline dropwise. The reaction mixture was stirred for 20 minutes and then treated with a solution of 0.9 g (5.3 mmol) of 4-fluoro-(N-methyl-N-methoxy)-benzamide in THF. The reaction mixture was warmed to 0C and quenched by addition of 10 mL of brine. The mixture was extracted with ethyl acetate (3 x 10 mL) and the combined organic phases were dried over MgSO4. The mixture was filtered and the filtrate was concentrated in vacuo to give the title compound as an orange solid. H1 NMR (CDCl3 300 MHz): 4.23 s (d, 2H), 7.1-7.18 m (4H), 8.02 (dd, 2H), 8.55 (dd, 2H).
  • 2
  • [ 116332-54-8 ]
  • [ 6576-05-2 ]
YieldReaction ConditionsOperation in experiment
100% To A solution OF DIISOPROPYLAMINE (23. 4 ML, 165. 7 MMOL) IN THF (250 ML), COOLED TO-78 C, BULI (103. 5 ML OF A 1. 6 M SOLUTION IN HEXANE, 165. 7 MMOL) WAS ADDED dropwise under argon atmosphere. After 5 minutes, A solution OF 4-METHYLPYRIDINE (10. 28 G, 110. 4 MMOL) IN THF (85 ML) WAS ADDED OVER 20 min. The mixture was stirred at 0C for 15 min and A solution OF 4-FLUORO-N-METHOXY-N-METHYLBENZAMIDE (obtained in section A) in THF (85 ML) was added over 30 min period. The REACTION WAS ALLOWED TO REACH ROOM TEMPERATURE. WATER (100 ML) AND ETOAC (100 ML) were added and the mixture was stirred for 30 min. The organic phase was separated, dried over NA2S04 and concentrated to dryness, to afford 24. 32 G OF the desired compound (YIELD : 100%). H NMR (300 MHz, CDCI3) 5 (TMS) : 4. 29 (S, 2 H), 7.14 - 7.23 (complex signal, 4 H), 8. 05 (M, 2 H), 8.59 (dd, Jo = 1.6 Hz, Jm = 4.4 Hz, 2 H).
  • 3
  • [ 108-89-4 ]
  • [ 100-41-4 ]
  • [ 116332-54-8 ]
  • [ 6576-05-2 ]
YieldReaction ConditionsOperation in experiment
With lithium diisopropyl amide; In tetrahydrofuran; n-heptane; Step 1. 1-(4-fluorophenyl)-2-(4-pyridinyl)-ethanone To a solution of lithium diisopropyl amide (2.0 M in heptane, tetrahydrofuran, ethyl benzene) 3.1 mL (6.3 mmol) in 6 mL of anhydrous tetrahydrofuran at -78 C. under nitrogen was added 0.5 g (5.3 mmol) of 4-picoline dropwise. The reaction mixture was stirred for 20 minutes and then treated with a solution of 0.9 g (5.3 mmol) of 4-fluoro-(N-methyl-N-methoxy)-benzamide in tetrahydrofuran. The reaction mixture was warmed to 0 C. and quenched by addition of 10 mL of brine. The mixture was extracted with ethyl acetate (3*10 mL) and the combined organic phases were dried over MgSO4. The mixture was filtered and the filtrate was concentrated in vacuo to give the title compound as an orange solid. H1 NMR (CDCl3 300 MHz): 4.23 s (d, 2H), 7.1-7.18 m (4H), 8.02 (dd, 2H), 8.55 (dd, 2H).
With lithium diisopropyl amide; In tetrahydrofuran; n-heptane; Step 1. 1-(4-fluorophenyl)-2-(4-pyridinyl)-ethanone To a solution of lithium diisopropyl amide (2.0 M in heptane, tetrahydrofuran, ethyl benzene) 3.1 mL (6.3 mmol) in 6 mL of anhydrous tetrahydrofuran at -78 C. under nitrogen was added 0.5 g (5.3 mmol) of 4-picoline dropwise. The reaction mixture was stirred for 20 minutes and then treated with a solution of 0.9 g (5.3 mmol) of 4-fluoro-(N-methyl-N-methoxy)-benzamide in tetrahydrofuran. The reaction mixture was warmed to 0 C. and quenched by addition of 10 mL of brine. The mixture was extracted with ethyl acetate (3*10 mL) and the combined organic phases were dried over MgSO4. The mixture was filtered and the filtrate was concentrated in vacuo to give the title compound as an orange solid. H1NMR (CDCl3300 MHz): 4.23 s (d, 2H), 7.1-7.18 m (4H), 8.02 (dd, 2H), 8.55 (dd, 2H).
  • 4
  • [ 108-89-4 ]
  • THF ethyl benzene [ No CAS ]
  • [ 116332-54-8 ]
  • [ 6576-05-2 ]
YieldReaction ConditionsOperation in experiment
With lithium diisopropyl amide; In tetrahydrofuran; n-heptane; Step 1 1-(4-fluorophenyl)-2-(4-pyridyl)-ethanone STR39 To a solution of lithium diisopropyl amide (Aldrich Chemical Co. 2.0M in heptane, THF ethyl benzene) 3.1 mL (6.3 mmol) in 6 mL of anhydrous THF at -78 C. under nitrogen was added 0.5 g (5.3 mmol) of 4-picoline dropwise. The reaction mixture was stirred for 20 minutes and then treated with a solution of 0.9 g (5.3 mmol) of 4-fluoro-(N-methyl-N-methoxy)-benzamide in THF. The reaction mixture was warmed to 0 C. and quenched by addition of 10 mL of brine. The mixture was extracted with ethyl acetate (3*10 mL) and the combined organic phases were dried over MgSO4. The mixture was filtered and the filtrate was concentrated in vacuo to give the title compound as an orange solid. H1 NMR (CDCl3 300 MHz): 4.23 s (d, 2H), 7.1-7.18 m (4H), 8.02 (dd, 2H), 8.55 (dd, 2H).
 

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