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Chemical Structure| 18503-89-4 Chemical Structure| 18503-89-4

Structure of 18503-89-4

Chemical Structure| 18503-89-4

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Product Details of [ 18503-89-4 ]

CAS No. :18503-89-4
Formula : C9H21NO2
M.W : 175.27
SMILES Code : CN(C)C(OC(C)C)OC(C)C
MDL No. :MFCD00008879
InChI Key :XOZZATXWQMOVHL-UHFFFAOYSA-N
Pubchem ID :87682

Safety of [ 18503-89-4 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H225-H315-H319-H335
Precautionary Statements:P210-P233-P240-P241-P242-P243-P261-P264-P271-P280-P303+P361+P353-P304+P340+P312-P305+P351+P338-P332+P313-P337+P313-P370+P378-P403+P233-P403+P235-P405-P501
Class:3
UN#:1993
Packing Group:

Application In Synthesis of [ 18503-89-4 ]

* 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 [ 18503-89-4 ]
  • Downstream synthetic route of [ 18503-89-4 ]

[ 18503-89-4 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 18503-89-4 ]
  • [ 502496-34-6 ]
  • [ 885520-59-2 ]
YieldReaction ConditionsOperation in experiment
68%
Stage #1: With triethylamine In N,N-dimethyl-formamide at 130℃; for 2 h;
Stage #2: With iron; acetic acid In toluene at 100℃; for 0.5 h;
A dry 100-mL round bottom flask is charged with 4-bromo-2-fluoro-6- nitrotoluene (1.3 g; 5.56 mmol; 1 eq.), A/,A/-dimethylformamide diisopropyl acetal (2.6 mL; 12.22 mmol; 2.2 eq.), triethylamine (0.85 mL; 6.1 1 mmol; 1.1 eq.), anhydrous DMF (5 mL) and the mixture is stirred at 130 °C for 2 h. After removal of the solvent, the residue is dissolved in a mixture of toluene (30 mL) and acetic acid (40 mL), followed by the addition of iron (6.2 g; 1 1 1.10 mmol; 20 eq.) and silica (6 g). The dark red mixture is heated to 100 °C with vigorous stirring, for 30 min. The mixture is then cooled to room temperature, diluted with EtOAc, filtered and the solids are thoroughly washed with EtOAc. The combined filtrates are washed with sat. aq. Na2S20s, sat. aq. NaHCG-3 and brine, dried over Na2S04 and concentrated in vacuo. The residue is purified by FCC (20percent DCM in hexanes) to afford 6-bromo-4-fluoro-1 /-/-indole (814 mg; 3.75 mmol; 68percent; UPLC purity: 99percent).
References: [1] Patent: WO2016/180537, 2016, A1, . Location in patent: Page/Page column 181; 182.
[2] ChemMedChem, 2019, vol. 14, # 1, p. 169 - 181.
  • 2
  • [ 18503-89-4 ]
  • [ 1143026-45-2 ]
  • [ 1245643-61-1 ]
References: [1] Journal of Medicinal Chemistry, 2014, vol. 57, # 14, p. 6128 - 6140.
 

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