Triethylsilane → 1-(5-(2-Bromoethyl)indolin-1-yl)ethanone

HRID 535672Notes

Reaction equation

HRID 535672 reaction equation
C([SiH](CC)CC)C.[C:8]([N:11]1[C:19]2[C:14](=[CH:15][C:16]([C:20](=O)[CH2:21][Br:22])=[CH:17][CH:18]=2)[CH2:13][CH2:12]1)(=[O:10])[CH3:9]>FC(F)(F)C(O)=O>[Br:22][CH2:21][CH2:20][C:16]1[CH:15]=[C:14]2[C:19](=[CH:18][CH:17]=1)[N:11]([C:8](=[O:10])[CH3:9])[CH2:12][CH2:13]2

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 197113291-(1-acetyl-2,3-dihydro-1H-indol-5-yl)-2-bromoethanone

Product 1

HCID 517132361-(5-(2-Bromoethyl)indolin-1-yl)ethanone

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
55 °C

Procedure

Triethylsilane (8.8 mL, 54.9 mmol) was added to a solution of 1-(1-acetylindolin-5-yl)-2-bromo-ethanone (1.9 g, 6.73 mmol) in trifluoroacetic acid (70 mL) at rt. The mixture was heated at 55° C. for 18 h, then cooled and concentrated under reduced pressure. The product was purified by flash chromatography (SiO2; hexane/EtOAc; 75/25). Yield: 1.2 g (67%).

Workup

  1. temperaturecooled
  2. concentrationconcentrated under reduced pressure
  3. customThe product was purified by flash chromatography (SiO2; hexane/EtOAc; 75/25)

Sources & evidence

ORD record
ord-c570a7dbf4b74f799e44f48404509d05
Source dataset
uspto-grants-2014_10
Patent number
US08859534B2

Reaction notes

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