Hydrochloric Acid → HCID 57658763, compound

HRID 910020Notes

Reaction equation

HRID 910020 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:5]([O:6][CH2:7][C:8]#[N:9])=[C:4]([C:12]([C:14]2[CH:15]=[N:16][N:17]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH:18]=2)=[O:13])[CH:3]=1.[N-:25]=[N+:26]=[N-:27].[Na+].C(O)(C)C.Cl>[Zn+2].[Br-].[Br-].CCOC(C)=O.O>[Br:1][C:2]1[CH:11]=[CH:10][C:5]([O:6][CH2:7][C:8]2[N:25]=[N:26][NH:27][N:9]=2)=[C:4]([C:12]([C:14]2[CH:15]=[N:16][N:17]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH:18]=2)=[O:13])[CH:3]=1

Participants

8

Reactant 4

HCID 313Hydrochloric Acid2×HCID 3776IsopropanolHCID 33557Sodium AzideHCID 57658838HCID 57658838, compound

Product 1

HCID 57658763HCID 57658763, compoundYield 111.2%

Reagents, catalysts & solvents 3

HCID 10421208Zinc bromideCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

[4-Bromo-2-(1-phenyl-1H-pyrazole-4-carbonyl)phenoxy]-acetonitrile (38 mg) was added NaN3 (66 mg), ZnBr2 (59 mg), isopropanol (1.3 mL) and water (1.6 mL), and the reaction mixture was heated to reflux for 1 h. The mixture was added 3% HCl (1 mL) and EtOAc (4 mL) and stirred until two clear phases appeared. The aqueous phase was added 3% HCl until pH<1 and extracted with EtOAc. The combined organic phases were washed with brine, dried (MgSO4) and concentrated to give 47 mg white foam: LC/MS (an10n8): Rt 2.93, m/z 243.0 [M−H]−; 1H NMR (CDCl3): δ 5.69 (s, 2H), 7.13 (d, J=8.6 Hz, 1H), 7.39-7.45 (m, 1H), 7.49-7.56 (m, 2H), 7.62-7.71 (m, 2H), 7.71-7.79 (m, 1H), 8.13 (s, 1H), 8.45 (s, 1H); 13C NMR (CDCl3): δ 63.3, 115.6, 117.7, 120.3, 124.5, 128.6, 130.0, 131.2, 132.0, 132.9, 136.3, 139.1, 143.5, 154.7, 188.4.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for 1 h
  3. extractionextracted with EtOAc
  4. washThe combined organic phases were washed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-002cd7e87c5d4ffd9f49c8cfb3880272
Source dataset
uspto-grants-2011_09
Patent number
US08022063B2

Reaction notes

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