1,8-Diazabicyclo(5.4.0)undec-7-ene → 4-(azidomethyl)-1H-indole

HRID 1058371Notes

Reaction equation

HRID 1058371 reaction equation
[NH:1]1[C:9]2[CH:8]=[CH:7][CH:6]=[C:5]([CH2:10]O)[C:4]=2[CH:3]=[CH:2]1.C1(P([N:26]=[N+:27]=[N-:28])(C2C=CC=CC=2)=O)C=CC=CC=1.N12CCCN=C1CCCCC2>O1CCCC1>[N:26]([CH2:10][C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:4]=1[CH:3]=[CH:2][NH:1]2)=[N+:27]=[N-:28]

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 199401P,P-Diphenylphosphinic azideHCID 27734571H-indol-4-ylmethanol

Product 1

HCID 226613274-(azidomethyl)-1H-indoleYield 1,810.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1H-indole-4-methanol (Example 17; 71 mg, 0.48 mmol) in tetrahydrofuran (1 mL) at 0° C. was added diphenylphosphoryl azide (156 μL, 0.72 mmol) followed by 1,8-diazabicyclo[5.4.0]undec-7-ene (87.4 μL, 0.58 mmol). The cooling bath was removed and the solution was allowed to stir for 5 h. After the solvent was evaporated, ethyl acetate was added and the solution was washed with 1N hydrochloric acid solution and brine, dried (MgSO4), filtered and concentrated. The residual material was chromatographed over silica gel (12% ethyl acetateihexanes) to give 4-(azidomethyl)-1H-indole (1.496 g, 88% yield) as an oil.

Workup

  1. customThe cooling bath was removed
  2. customAfter the solvent was evaporated
  3. additionethyl acetate was added
  4. washthe solution was washed with 1N hydrochloric acid solution and brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residual material was chromatographed over silica gel (12% ethyl acetateihexanes)

Sources & evidence

ORD record
ord-4429e7c72f6147a79a9392360b8cbaed
Source dataset
uspto-grants-2003_02
Patent number
US06515124B2

Reaction notes

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