Triethylamine → 1H-Indole-3-carbonyl azide

HRID 1510216Notes

Reaction equation

HRID 1510216 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]([OH:12])=O)=[CH:2]1.C(N(CC)CC)C.C1(P([N:34]=[N+:35]=[N-:36])(C2C=CC=CC=2)=O)C=CC=CC=1.C(OCC)(=O)C>O1CCCC1>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]([N:34]=[N+:35]=[N-:36])=[O:12])=[CH:2]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 69867Indole-3-Carboxylic AcidHCID 199401P,P-Diphenylphosphinic azide

Product 1

HCID 122437911H-Indole-3-carbonyl azide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 1H-indole-3-carboxylic acid (500 mg) in tetrahydrofuran (10 mL) were added triethylamine (0.519 mL) and diphenylphosphoryl azide (0.802 mL) at ambient temperature. The mixture was stirred at 60° C. for 2 hours. Ethyl acetate (10 mL) was added to the mixture at room temperature, and then the organic layer was washed with saturated sodium bicarbonate aqueous solution×2, water and brine, dried over magnesium sulfate, and concentrated in vacuo. The residual solid was recrystallized from ethyl acetate (2 mL). The crystals were washed with n-hexane/chloroform (3:1, 1 mL). The crystals were recrystallized from ethyl acetate again to afford 1H-indole-3-carbonyl azide (192 mg) as white crystals.

Workup

  1. washthe organic layer was washed with saturated sodium bicarbonate aqueous solution×2, water and brine
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe residual solid was recrystallized from ethyl acetate (2 mL)
  5. washThe crystals were washed with n-hexane/chloroform (3:1, 1 mL)
  6. customThe crystals were recrystallized from ethyl acetate again

Sources & evidence

ORD record
ord-4387e41354884dc980676702bac3d2df
Source dataset
uspto-grants-2012_07
Patent number
US08211919B2

Reaction notes

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