Triethylsilane → HCID 57608623, compound

HRID 1015442Notes

Reaction equation

HRID 1015442 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([C:17]([O:19][CH3:20])=[O:18])=[CH:14][CH:15]=2)[C:10]([CH:21]=O)=[CH:9]1)[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][CH3:20])=[O:18])=[CH:14][CH:15]=2)[CH:10]([CH3:21])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 86628479HCID 86628479, compound

Product 1

HCID 57608623HCID 57608623, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A 500 mg portion of methyl 1-benzyl-3-formyl-1H-indole-5-carboxylate was dissolved in 17 ml of trifluoroacetic acid, and 2.70 ml of triethylsilane was added at 0° C., followed by stirring at room temperature for 3 hours. After evaporation of the solvent, ethyl acetate was added thereto, followed by washing with water, a saturated sodium bicarbonate 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 433 mg of methyl 1-benzyl-3-methylindoline-5-carboxylate as a pale yellow liquid.

Workup

  1. customAfter evaporation of the solvent, ethyl acetate
  2. additionwas added
  3. washby washing with water
  4. dry with materiala saturated sodium bicarbonate aqueous solution and saturated brine and subsequent 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-df21d64c498c4ac49e87df68cdc146bf
Source dataset
uspto-grants-2011_07
Patent number
US07985764B2

Reaction notes

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