Triethylamine hydrochloride → HCID 178505847, compound

HRID 394583Notes

Reaction equation

HRID 394583 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=1)[CH:7]=[CH:6]2)#[N:2].Cl.C(N(CC)CC)C.[N-:27]=[N+:28]=[N-:29].[Na+]>COCCOC>[F:18][C:15]1[CH:16]=[CH:17][C:12]([N:8]2[C:9]3[C:5](=[CH:4][C:3]([C:1]4[NH:29][N:28]=[N:27][N:2]=4)=[CH:11][CH:10]=3)[CH:6]=[CH:7]2)=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 11130Triethylamine hydrochlorideHCID 33557Sodium AzideHCID 150064291-(4-fluorophenyl)-5-cyano-1H-indole

Product 1

HCID 178505847HCID 178505847, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A suspension of 5-cyano-1-(4-fluorophenyl)-1H-indole (20 g) (prepared according to the method in Perregaard et al. J. Med. Chem. 1992 (35), 1092-1101), triethylamine hydrochloride (35 g) and sodium azide (20 g) in DME (250 mL) was boiled at reflux for 16 hours. Inorganic salts were filtered off and the solvent evaporated in vacuo. The remaining solid material was dissolved in ethyl acetate (500 mL) and water (500 mL) and glacial acetic acid was added. The organic phase was worked-up according to the general procedure above yielding 19 g of crystalline title compound 8a, mp 224-225° C. (washed with diethyl ether).

Workup

  1. customprepared
  2. temperatureat reflux for 16 hours
  3. filtrationInorganic salts were filtered off
  4. customthe solvent evaporated in vacuo
  5. dissolutionThe remaining solid material was dissolved in ethyl acetate (500 mL)
  6. additionwater (500 mL) and glacial acetic acid was added
  7. customabove yielding
  8. wash19 g of crystalline title compound 8a, mp 224-225° C. (washed with diethyl ether)

Sources & evidence

ORD record
ord-730beb1a9dc6452d8cfc984ce97552ee
Source dataset
uspto-grants-2003_08
Patent number
US06602889B1

Reaction notes

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