Hydrochloric Acid → HCID 178420162, compound

HRID 2409974Notes

Reaction equation

HRID 2409974 reaction equation
[CH:1]1([C:4]2[CH:12]=[C:11]3[C:7]([C:8]([CH2:19][C:20]4[N:25]=[C:24]([C:26]#[N:27])[CH:23]=[CH:22][CH:21]=4)=[C:9]([C:13]4[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=4)[NH:10]3)=[CH:6][CH:5]=2)[CH2:3][CH2:2]1.[N-:28]=[N+:29]=[N-:30].[Na+].C(O)(C)C.Cl>[Br-].[Zn+2].[Br-].O>[CH:1]1([C:4]2[CH:12]=[C:11]3[C:7]([C:8]([CH2:19][C:20]4[CH:21]=[CH:22][CH:23]=[C:24]([C:26]5[NH:30][N:29]=[N:28][N:27]=5)[N:25]=4)=[C:9]([C:13]4[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=4)[NH:10]3)=[CH:6][CH:5]=2)[CH2:2][CH2:3]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3776IsopropanolHCID 33557Sodium AzideHCID 86703283HCID 86703283, compound

Product 1

HCID 178420162HCID 178420162, compoundYield 85.4%

Reagents, catalysts & solvents 2

HCID 10421208Zinc bromideCatalystHCID 962WaterSolvent

Procedure

To a mixture of 6-(6-cyclopropyl-2-phenyl-1H-indol-3-ylmethyl)pyridine-2-carbonitrile (93 mg), sodium azide (86.5 mg), isopropyl alcohol (3.2 mL), and water (2.1 mL) was added zinc bromide (74.9 mg), and this mixture was heated under reflux for 23 hours while stirring. The reaction mixture was left to be cooled. To the reaction mixture was added 1 mol/L hydrochloric acid, followed by extraction with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: methanol-dichloromethane) to obtain the title compound (89.2 mg).

Workup

  1. temperaturethis mixture was heated
  2. temperatureunder reflux for 23 hours
  3. waitThe reaction mixture was left
  4. temperatureto be cooled
  5. extractionfollowed by extraction with ethyl acetate
  6. washThe organic layer was washed with saturated brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (eluting solvent: methanol-dichloromethane)

Sources & evidence

ORD record
ord-eac306127bf24b96af10739e95f11421
Source dataset
uspto-grants-2014_08
Patent number
US08815903B2

Reaction notes

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