Water → HCID 131719929, compound

HRID 976592Notes

Reaction equation

HRID 976592 reaction equation
C(C1C=CC=CC=1[C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([CH:18]([C:23]1[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][CH:24]=1)[CH2:19][CH2:20][CH2:21][CH3:22])[CH:13]=[CH:12]2)#N.C(#N)C.O>C(O)(=O)C>[F:32][C:29]([F:30])([F:31])[C:26]1[CH:27]=[CH:28][C:23]([CH:18]([N:14]2[C:15]3[C:11](=[CH:10][CH:9]=[CH:17][CH:16]=3)[CH:12]=[CH:13]2)[CH2:19][CH2:20][CH2:21][CH3:22])=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6342AcetonitrileHCID 21468877HCID 21468877, compound

Product 1

HCID 131719929HCID 131719929, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
95 °C

Procedure

5-(2-Cyanophenyl)-1-[1-(4-trifluoromethylphenyl)-1pentyl]indole (1.9 moles, 800 mg) was dissolved in 2.0 g of tributyltinazide and heated at 95° C. for 24 hours. The solution was cooled. Acetonitrile, water, and acetic acid (50 ml of 8:1:1) were added. The acetonitrile solution was washed with hexane, concentrated, diluted with ethyl acetate, washed with water, dried over sodium sulfate and concentrated. The product was chromatographed on silica gel eluted with ethyl acetate to yield 120 mg of 5-[2-tetrazol-5-yl)phenyl]-1-[1-(4- trifluoromethylphenyl)-1-pentyl]indole.

Workup

  1. temperatureThe solution was cooled
  2. washThe acetonitrile solution was washed with hexane
  3. concentrationconcentrated
  4. additiondiluted with ethyl acetate
  5. washwashed with water
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated
  8. customThe product was chromatographed on silica gel
  9. washeluted with ethyl acetate

Sources & evidence

ORD record
ord-93ae78f6bd974f88afc88926ca29b73d
Source dataset
uspto-grants-1997_03
Patent number
US05612360

Reaction notes

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