Triethylamine hydrochloride → HCID 178462514, compound

HRID 502121Notes

Reaction equation

HRID 502121 reaction equation
[CH2:1]([N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[C:5]([C:14]#[N:15])=[CH:4]1)[CH3:2].Cl.C(N(CC)CC)C.[N-:24]=[N+:25]=[N-:26].[Na+]>C1(C)C=CC=CC=1.C([O-])(O)=O.[Na+]>[CH2:1]([N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[C:5]([C:14]2[NH:26][N:25]=[N:24][N:15]=2)=[CH:4]1)[CH3:2]

Participants

6

Reactant 3

HCID 11130Triethylamine hydrochlorideHCID 33557Sodium AzideHCID 116441001-ethyl-6-methoxy-1H-indole-3-carbonitrile

Product 1

HCID 178462514HCID 178462514, compoundYield 45.2%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A mixture of 1-ethyl-6-methoxy-1H-indole-3-carbonitrile (1.00 g, 5.00 mmol) in toluene (30 mL) is treated with triethylamine hydrochloride (1.03 g, 7.50 mmol) and sodium azide (0.49 g, 7.50 mmol) and is heated at reflux for 16 h. After cooling to room temperature, the reaction mixture is diluted with saturated NaHCO3 and extracted with EtOAc. The organic layer is then washed with additional NaHCO3 (2×). The combined aqueous phases are acidified to pH 2 with 6N HCl. The resultant thick precipitate is extracted with hot EtOAc (3×) and the combined organic phases are washed with saturated NaCl and dried and concentrated to give 0.55 g (45%) of 1-ethyl-6-methoxy-3-(1H-tetrazol-5-yl)-1H-indole as a yellow solid.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 16 h
  3. extractionextracted with EtOAc
  4. washThe organic layer is then washed with additional NaHCO3 (2×)
  5. extractionThe resultant thick precipitate is extracted with hot EtOAc (3×)
  6. washthe combined organic phases are washed with saturated NaCl
  7. customdried
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-5cefb58b3d45487faa36736097dbf17f
Source dataset
uspto-grants-2010_08
Patent number
US07772271B2

Reaction notes

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