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Chemical Structure| 17826-04-9 Chemical Structure| 17826-04-9
Chemical Structure| 17826-04-9

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CAS No.: 17826-04-9

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Synonyms: 6-Bromoindole-3-carboxaldehyde

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Product Details of 6-Bromo-1H-indole-3-carbaldehyde

CAS No. :17826-04-9
Formula : C9H6BrNO
M.W : 224.05
SMILES Code : O=CC1=CNC2=C1C=CC(Br)=C2
Synonyms :
6-Bromoindole-3-carboxaldehyde
MDL No. :MFCD00792689
InChI Key :WCCLQCBKBPTODV-UHFFFAOYSA-N
Pubchem ID :2794830

Safety of 6-Bromo-1H-indole-3-carbaldehyde

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

Application In Synthesis of 6-Bromo-1H-indole-3-carbaldehyde

* 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.

  • Upstream synthesis route of [ 17826-04-9 ]
  • Downstream synthetic route of [ 17826-04-9 ]

[ 17826-04-9 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 17826-04-9 ]
  • [ 224434-83-7 ]
References: [1] Bioorganic and Medicinal Chemistry Letters, 1999, vol. 9, # 4, p. 569 - 572.
[2] Bioorganic and Medicinal Chemistry, 2000, vol. 8, # 2, p. 363 - 371.
[3] Patent: WO2010/151737, 2010, A2, . Location in patent: Page/Page column 142.
[4] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 19, p. 5897 - 5900.
[5] CrystEngComm, 2013, vol. 15, # 37, p. 7490 - 7497.
  • 2
  • [ 67-56-1 ]
  • [ 17826-04-9 ]
  • [ 868656-97-7 ]
YieldReaction ConditionsOperation in experiment
51%
Stage #1: at 20℃; for 0.0833333 h;
Stage #2: at 20℃; Inert atmosphere		 13b) Methyl -bromo-lH-indole-S-carboxylateTo a stirred solution of -bromo-lH-indole-S-carbaldehyde (1.6 g, 7.1 mmol) in methanol (70 mL) was added sodium cyanide (1.7 g, 34.7 mmol) at room temperature. The reaction mixture was stirred for five minutes and then manganese (IV) oxide (7.4 g, 85.1 mmol) was added portionwise over a period of 2.5 hours. The reaction mixture was stirred overnight at room temperature under a nitrogen atmosphere. To the reaction mixture was added dichloromethane (75 mL). The reaction mixture was filtered through a pad of Celite.(R). and the pad was washed with <n="104"/>dichloromethane. The cloudy filtrate was concentrated in vacuo and the residue was partitioned between water and ethyl acetate. The organic phase was separated, washed with water, dried over magnesium sulfate, filtered, and the filtrate was concentrated to give the crude product as an off-white solid. The crude product was purified by flash chromatography over silica gel with a hexanes: ethyl acetate gradient (100:0 to 0: 100) to give 0.636 g (51percent based on recovered starting material) of methyl 6-bromo-lH-indole-3-carboxylate as an off-white solid. 1H NMR (J6-DMSO, 400 MHz): δ 12.02 (br s, IH), 8.09 (s, IH), 7.90 (d, J = 9 Hz, IH), 7.65 (d, J = 2 Hz, IH), 7.31 (dd, J = 9, 2 Hz, IH), 3.78 (s, 3H). ES-LCMS m/z 252 (M - H)".
References: [1] Patent: WO2008/157270, 2008, A1, . Location in patent: Page/Page column 102-103.
 

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