Hydrochloric Acid → HCID 178487105, compound

HRID 2400283Notes

Reaction equation

HRID 2400283 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:12][C:13]1[N:18]=[C:17]([C:19]#[N:20])[CH:16]=[CH:15][CH:14]=1)[C:7]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[CH:6]2.C(O)(C)C.[N-:31]=[N+:32]=[N-:33].[Na+].Cl>C(OCC)(=O)C.[Br-].[Zn+2].[Br-].O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:12][C:13]1[CH:14]=[CH:15][CH:16]=[C:17]([C:19]3[NH:33][N:32]=[N:31][N:20]=3)[N:18]=1)[C:7]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[CH:6]2

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 3776IsopropanolHCID 33557Sodium AzideHCID 867079356-(5-Methoxy-2-phenylindol-1-ylmethyl)pyridine-2-carbonitrile

Product 1

HCID 178487105HCID 178487105, compoundYield 82.2%

Reagents, catalysts & solvents 3

HCID 10421208Zinc bromideCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 6-(5-methoxy-2-phenylindol-1-ylmethyl)pyridine-2-carbonitrile (95 mg), isopropyl alcohol (6 mL), and water (4 mL) were added sodium azide (36 mg) and zinc bromide (32 mg). This mixture was stirred overnight while heated to reflux. The reaction mixture was left to cool to room temperature, and then diluted with ethyl acetate. To the mixture was added 2 mol/L hydrochloric acid (4 mL), followed by stirring at room temperature for 30 minutes. The organic layer was separated, and the aqueous layer was extracted with ethyl acetate. The combined organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: dichloromethane-methanol) to obtain the title compound (88 mg). 1H-NMR (DMSO-d6) δ ppm: 3.78 (3H, s), 5.61 (2H, s), 6.54 (1H, d, J=7.8 Hz), 6.66 (1H, d, J=0.4 Hz), 6.78 (1H, dd, J=2.5, 8.9 Hz), 7.16 (1H, d, J=2.5 Hz), 7.29 (1H, d, J=8.9 Hz), 7.35-7.55 (5H, m), 7.90 (1H, t, J=7.8 Hz), 8.05 (1H, d, J=7.8 Hz). ESI-MS (m/z): 383 (M+H)+

Workup

  1. temperaturewhile heated to reflux
  2. waitThe reaction mixture was left
  3. stirringby stirring at room temperature for 30 minutes
  4. customThe organic layer was separated
  5. extractionthe aqueous layer was extracted with ethyl acetate
  6. washThe combined organic layer was washed with saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (eluting solvent: dichloromethane-methanol)

Sources & evidence

ORD record
ord-e5271f95b21947ae86ed22d13bad322d
Source dataset
uspto-grants-2014_08
Patent number
US08796247B2

Reaction notes

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