Triethylsilane → HCID 57608633, compound

HRID 1015437Notes

Reaction equation

HRID 1015437 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:14][CH:15]=2)[C:10]([CH3:22])=[C:9]1[CH3:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([SiH](CC)CC)C>FC(F)(F)C(O)=O>[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:14][CH:15]=2)[CH:10]([CH3:22])[CH:9]1[CH3:23])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 2838501HCID 2838501, compound

Product 1

HCID 57608633HCID 57608633, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
50 °C

Procedure

A 460 mg portion of ethyl 1-benzyl-2,3-dimethyl-1H-indole-5-carboxylate was dissolved in 15 ml of trifluoroacetic acid, and 1.19 ml of triethylsilane was added at room temperature, followed by stirring at 50° C. for 3 hours. After evaporation of the solvent, ethyl acetate was added, followed by washing with a 1 M sodium hydroxide aqueous solution and saturated brine and subsequent drying over anhydrous sodium sulfate. After evaporation of the solvent, the residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:30 to 1:20) to obtain 437 mg of ethyl 1-benzyl-2,3-dimethylindoline-5-carboxylate as a pale yellow liquid.

Workup

  1. customAfter evaporation of the solvent, ethyl acetate
  2. additionwas added
  3. washby washing with a 1 M sodium hydroxide aqueous solution and saturated brine
  4. dry with materialsubsequent drying over anhydrous sodium sulfate
  5. customAfter evaporation of the solvent
  6. customthe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:30 to 1:20)

Sources & evidence

ORD record
ord-7473b195841543868c9486b3d1d66fa1
Source dataset
uspto-grants-2011_07
Patent number
US07985764B2

Reaction notes

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