Triethylsilane → 1-[5-(2-Bromopropyl)-2,3-dihydro-1H-indol-1-yl]ethanone

HRID 273842Notes

Reaction equation

HRID 273842 reaction equation
[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([C:13](=O)[CH:14]([Br:16])[CH3:15])=[CH:10][CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].C([SiH](CC)CC)C>FC(F)(F)C(O)=O>[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([CH2:13][CH:14]([Br:16])[CH3:15])=[CH:10][CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 20094393HCID 20094393, compound

Product 1

HCID 200943701-[5-(2-Bromopropyl)-2,3-dihydro-1H-indol-1-yl]ethanoneYield 76.5%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of 1-acetyl-5-(2-bromopropionyl)indoline (210 g) in trifluoroacetic acid (700 ml) was added triethylsilane (190 g) over a period of 30 minutes with stirring under ice cooling, the mixture was stirred for 30 minutes under ice cooling, and then for 1 hour at room temperature. After the reaction mixture was concentrated under reduced pressure, the residue was poured into water (2 l), and to the mixture was added hexane (500 ml) and stirred. The precipitates were collected by filtration, washed with hexane, and recrystallized from ethyl acetate-hexane to give 153 g of 1-acetyl-5-(2-bromopropyl)indoline melting at 124°-126° C.

Workup

  1. stirringthe mixture was stirred for 30 minutes under ice cooling
  2. concentrationAfter the reaction mixture was concentrated under reduced pressure
  3. additionthe residue was poured into water (2 l)
  4. additionto the mixture was added hexane (500 ml)
  5. stirringstirred
  6. filtrationThe precipitates were collected by filtration
  7. washwashed with hexane
  8. customrecrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-6db7ef8e56644148954d7d9b13f4e8bb
Source dataset
uspto-grants-1995_02
Patent number
US05387603

Reaction notes

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