Dabco → Indole

HRID 2393771Notes

Reaction equation

HRID 2393771 reaction equation
[CH3:1][Si:2]([CH3:13])([CH3:12])[C:3]1[NH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.INC1C=CC=CC=1.C1N2CCN(CC2)C1>CN(C=O)C.CC(O)=O.CC(O)=O.[Pd]>[CH3:1][Si:2]([CH3:13])([CH3:12])[C:3]1[NH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[NH:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:11]=[CH:3]1

Participants

7

Reactant 3

HCID 9237DabcoHCID 10921317Trimethylsilyl indoleHCID 18447960Iodoaniline

Product 2

HCID 798IndoleHCID 10921317Trimethylsilyl indole

Reagents, catalysts & solvents 2

HCID 4144353Palladium (II) acetateCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
105 °C

Procedure

Preparation of 2-trimethylsilyl indole ##STR15## A mixture of iodoaniline (2.19 g, 10 mmol), acyl silane (2.36 g, 20 mmol, prepared according to the procedures of reference example A), DABCO (1,4-diazabicyclo[2.2.2]octane, 3.36 g, 30 mmol) and Pd(OAC)2 (112.25 mg, 0.5 mmol) in 30 mL DMF was degassed via N2 /vacuum and heated at 105° C. for 36 h. The mixture was cooled to room temperature, diluted with IPAc (isopropyl acetate, 100 mL) and washed with 2×50 mL of water. The IPAc layer was concentrated in vacuum and chromatographed over silica gel to give 2-trimethylsilyl indole and indole.

Workup

  1. customprepared
  2. customwas degassed via N2 /vacuum
  3. temperatureThe mixture was cooled to room temperature
  4. additiondiluted with IPAc (isopropyl acetate, 100 mL)
  5. washwashed with 2×50 mL of water
  6. concentrationThe IPAc layer was concentrated in vacuum
  7. customchromatographed over silica gel

Sources & evidence

ORD record
ord-99d336822b7447189a1c0074f7ea2fb5
Source dataset
uspto-grants-1998_09
Patent number
US05808064

Reaction notes

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