Triethylamine hydrochloride → HCID 178462514, compound

HRID 907103Notes

Reaction equation

HRID 907103 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) was treated with triethylamine hydrochloride (1.03 g, 7.50 mmol) and sodium azide (0.49 g, 7.50 mmol) and was heated at reflux for 16 h. After cooling to room temperature, the reaction mixture was diluted with saturated NaHCO3 and extracted with EtOAc. The organic layer was then washed with additional NaHCO3 (2×). The combined aqueous phases were acidified to pH 2 with 6N HCl. The resultant thick precipitate was extracted with hot EtOAc (3×) and the combined organic phases were 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. temperaturewas heated
  2. temperatureat reflux for 16 h
  3. extractionextracted with EtOAc
  4. washThe organic layer was then washed with additional NaHCO3 (2×)
  5. extractionThe resultant thick precipitate was extracted with hot EtOAc (3×)
  6. washthe combined organic phases were washed with saturated NaCl
  7. customdried
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-d5482cd03475443ba75ff8a1ffcf14e0
Source dataset
uspto-grants-2011_09
Patent number
US08013006B2

Reaction notes

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