Sodium Azide → HCID 67617091, compound

HRID 1467998Notes

Reaction equation

HRID 1467998 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([NH2:10])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[N-:11]=[N+:12]=[N-:13].[Na+].[CH2:15](OC(OCC)(OCC)C)C>C(O)(=O)C>[N:10]1([C:6]2[CH:5]=[C:4]3[C:9](=[CH:8][CH:7]=2)[NH:1][CH:2]=[CH:3]3)[CH:15]=[N:13][N:12]=[N:11]1

Participants

5

Reactant 3

HCID 33557Sodium AzideHCID 66221Triethyl orthoacetateHCID 788675-Aminoindole

Product 1

HCID 67617091HCID 67617091, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

To a stirring solution of 1H-indol-5-amine (0.6 g, 4.52 mmol) in acetic acid (9 mL), sodium azide (0.42 g, 6.2 mmol) and triethoxy ethane (1.0 mL, 6.2 mmol) were added and stirred at 100° C. for 3 h. The reaction was brought to room temperature and stirred for 10-12 h. The reaction was quenched with saturated NaHCO3 and the mixture was extracted with ethyl acetate. The organic layer was separated, washed with brine, dried over anhydrous NaSO4 and concentrated in vacuo. Resultant residue was purified by flash column chromatography to yield 5-(1H-tetrazol-1-yl)-1H-indole. (0.174 g, 21%); MS: 186 (M+1).

Workup

  1. customwas brought to room temperature
  2. stirringstirred for 10-12 h
  3. customThe reaction was quenched with saturated NaHCO3
  4. extractionthe mixture was extracted with ethyl acetate
  5. customThe organic layer was separated
  6. washwashed with brine
  7. dry with materialdried over anhydrous NaSO4
  8. concentrationconcentrated in vacuo
  9. customResultant residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-cb06e4f5693c489aa70eb6b7b4b8df7c
Source dataset
uspto-grants-2015_04
Patent number
US09000175B2

Reaction notes

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