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Chemical Structure| 113423-51-1 Chemical Structure| 113423-51-1

Structure of 113423-51-1

Chemical Structure| 113423-51-1

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Product Details of [ 113423-51-1 ]

CAS No. :113423-51-1
Formula : C7H4Br2N2O
M.W : 291.93
SMILES Code : BrC1(Br)C(=O)NC2=NC=CC=C12
MDL No. :MFCD09028452
InChI Key :JHDQERQROBFSSO-UHFFFAOYSA-N
Pubchem ID :13864094

Safety of [ 113423-51-1 ]

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

Application In Synthesis of [ 113423-51-1 ]

* 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 [ 113423-51-1 ]

[ 113423-51-1 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 113423-51-1 ]
  • [ 5654-97-7 ]
YieldReaction ConditionsOperation in experiment
91% With acetic acid; zinc; In acetonitrile; 7-Azaoxindole 3,3-Dibromo-7-azaoxindole (2.9 g) was dissolved in a mixture of 20 mL of acetic acid and 30 mL of acetonitrile. To the solution was added 6.5 g of zinc dust. The mixture was stirred for 2 hrs at room temperature. The solid was filtered from the mixture and the solvent evaporated. The residue was slurried with ethyl acetate. The ethyl acetate solution containing insoluble solid was passed through a short column of silica gel. The collected ethyl acetate solution was evaporated and the residue dried under vacuum to give 1.8 g (yield 91%) of 7-azaoxindole acetic acid salt.
91% With acetic acid; zinc; In acetonitrile; 7-Azaoxindole 3,3-Dibromo-7-azaoxindole (2.9 g) was dissolved in a mixture of 20 mL of acetic acid and 30 mL of acetonitrile. To the solution was added 6.5 g of zinc dust. The mixture was stirred for 2 hrs at room temperature. The solid was filtered from the mixture and the solvent evaporated. The residue was slurried with ethyl acetate. The ethyl acetate solution containing insoluble solid was passed through a short column of silica gel. The collected ethyl acetate solution was evaporated and the residue dried under vacuum to give 1.8 g (yield 91%) of 7-azaoxindole acetic acid salt.
91% With acetic acid; zinc; In acetonitrile; at 20℃; for 2h; 7-Azaoxindole 3,3-Dibromo-7-azaoxindole (2.9 g) was dissolved in a mixture of 20 ML of acetic acid and 30 ML of acetonitrile.. To the solution was added 6.5 g of zinc dust.. The mixture was stirred for 2 hrs at room temperature.. The solid was filtered from the mixture and the solvent evaporated.. The residue was slurried with ethyl acetate.. The ethyl acetate solution containing insoluble solid was passed through a short column of silica gel.. The collected ethyl acetate solution was evaporated and the residue dried under vacuum to give 1.8 g (yield 91%) of 7-azaoxindole acetic acid salt.
76% General procedure: To a stirred solution of azaindole (10a or 10b, 12.7 mmol) in tert-butyl alcohol (100 mL) and H2O (100 mL) at room temperature, Br2 (2.6 mL, 50.5 mmol) was added dropwise over 20 min. The mixture was stirred for 1 h and the yellow precipitate (10b, or 11b) was collected by filtration. The dried precipitate (10b, or 11b, 4.8 mmol) was refluxed with 5% Pd-C (1.0 g) in 60 mL of 8.8% HCOOH/CH3OH for 12 h under nitrogen. The catalyst was removed by filtration through a pad of celite. After removal of the solvent, the residual was adjusted to pH 8-9 by addition of saturated K2CO3 solution. The solution was stored in the refrigerator overnight and the precipitate was filtered to give 5-azaindolin-2-one (10) or 7-azaindolin-2-one (11).
70% With ammonium chloride; zinc; In tetrahydrofuran; water; at 20℃; for 2h; b) 7-Azaoxindole A solution of 3,3-dibromo-7-azaoxindole (2.0 g, 7.2 mmol) in THF (50 ML) is stirred at room temperature and a saturated aqueous solution of NH4Cl is added.. Activated zinc powder is added and the reaction mixture is stirred for 2 h.. The zinc is removed by filtration through a pad of diatomaceous earth and the organic layer is separated.. The aqueous layer is extracted with THF (10 ML) and the combined organic layers are dried over anhydrous MgSO4, filtered and evaporated.. The residue is slurried in 10:1 CHCl3:MeOH (15 ML) and filtered through a pad of silica gel and the filtrate is evaporated.. The residue is triturated with water and the solid is collected by filtration and dried under vacuum to give 7-azaoxindole, 0.668 g (70%). 1H NMR (DMSO-d6) delta 10.94 (s, 1H), 8.02 (d, 1H, J=5.2 Hz), 7.52 (d, 1H, J=6.8 Hz), 6.90 (dd, 1H, J=6.8, 5.2 Hz), 3.53 (s, 2H). MS(AP-ve) 133 (100) (M-H)
Step 2: 1 ,3-Dihydro-pyrrolo[2,3-b]pyridin-2-oneTo a solution of 3,3-dibromo-1 ,3-dihydro-pyrrolo[2,3-b]pyridin-2-one (4.6 g, 15.76 mmol) in AcOH (80 ml) under N2 was added zinc powder (10.30 g, 10 eq). The mixture was stirred at RT for 30 min under N2 and then filtered through Celite (filter material) to remove the Zn. AcOH was removed in vacuo and the mixture was diluted with EtOAc and washed with NaHC03. The organic phase was separated dried(MgS04) and concentrated in vacuo to afford the title product; 1H NMR (400 MHz, DMSO-d6) delta 10.95 (1 H, s), 8.05(1 H, d), 7.55 (1 H, d), 6.95 (1 H, t), 3.55 (2H, s).

  • 2
  • [ 113423-51-1 ]
  • [ 7440-66-6 ]
  • [ 5654-97-7 ]
YieldReaction ConditionsOperation in experiment
With ammonium chloride; In tetrahydrofuran; CHCl3:MeOH; b 7-Azaoxindole A solution of 3,3-dibromo-7-azaoxindole (2.0 g, 7.2 mmol) in THF (50 mL) is stirred at room temperature and a saturated aqueous solution of NH4Cl is added. Activated zinc powder is added and the reaction mixture is stirred for 2 hours. The zinc is removed by filtration through a pad of diatomaceous earth and the organic layer is separated. The aqueous layer is extracted with THF (10 mL) and the combined organic layers are dried over anhydrous MgSO4, filtered and evaporated. The residue is slurried in 10:1 CHCl3:MeOH (15 mL) and filtered through a pad of silica gel and the filtrate is evaporated. The residue is triturated with water and the solid is collected by filtration and dried under vacuum to give 7-azaoxindole, 0.668 g (70%). 1H NMR (DMSO-d6) delta10.94 (s, 1H), 8.02 (d, 1H, J=5.2 Hz), 7.52 (d, 1H, J=6.8 Hz), 6.90 (dd, 1H, J=6.8, 5.2 Hz), 3.53 (s, 2H). MS(AP-ve) 133 (100) (M-H)
With ammonium chloride; In tetrahydrofuran; CHCl3:MeOH; b 1,3-Dihydro-2H-pyrrolo[2,3-b]pyridin-2-one A solution of 3,3-dibromo-1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-one (2.0 g, 7.2 mmol) in THF (50 mL) was stirred at room temperature, and a saturated aqueous solution of NH4Cl was added. Activated zinc powder was added, and the reaction mixture was stirred for 2 hours. The zinc was removed by filtration through a pad of diatomaceous earth, and the organic layer was separated. The aqueous layer was extracted with THF (10 mL), and the combined organic layers were dried over anhydrous MgSO4, filtered and evaporated. The residue was slurried in 10:1 CHCl3:MeOH (15 mL) and filtered through a pad of silica gel, and the filtrate was evaporated. The residue was triturated with water, and the solid was collected by filtration and dried under vacuum to give the title compound, 0.668 g (70%). 1H NMR (d6-DMSO) delta10.94 (s, 1H), 8.02 (d, 1H, J=5.2 Hz), 7.52 (d, 1H, J=6.8 Hz), 6.90 (dd, 1H, J=6.8, 5.2 Hz), 3.53 (s, 2H). MS (AP-ve) 133 (100) (M-H)
With ammonium chloride; In tetrahydrofuran; CHCl3:MeOH; b 1,3-Dihydro-2H-pyrrolo[2,3-b]pyridin-2-one A solution of 3,3-dibromo-1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-one (2.0 g, 7.2 mmol) in THF (50 mL) was stirred at room temperature, and a saturated aqueous solution of NH4Cl was added. Activated zinc powder was added, and the reaction mixture was stirred for 2 h. The zinc was removed by filtration through a pad of diatomaceous earth, and the organic layer was separated. The aqueous layer was extracted with THF (10 mL), and the combined organic layers were dried over anhydrous MgSO4, filtered and evaporated. The residue was slurried in 10:1 CHCl3:MeOH (15 mL) and filtered through a pad of silica gel, and the filtrate was evaporated. The residue was triturated with water, and the solid was collected by filtration and dried under vacuum to give the title compound, 0.668 g (70%). 1H NMR (d6-DMSO) delta 10.94 (s, 1H), 8.02 (d, 1H, J=5.2 Hz), 7.52 (d, 1H, J=6.8 Hz), 6.90 (dd, 1H, J=6.8, 5.2 Hz), 3.53 (s, 2H). MS (AP-ve) 133 (100) (M-H).
 

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