3-(4-(azidomethyl)phenyl)-1-(4-(perfluoroethoxy)phenyl)-1H-1,2,4-triazole → (4-(1-(4-(perfluoroethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)methanamine

HRID 62070Notes

Reaction equation

HRID 62070 reaction equation
[N:1]([CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:15]=[CH:14][N:13]([C:16]3[CH:21]=[CH:20][C:19]([O:22][C:23]([F:29])([F:28])[C:24]([F:27])([F:26])[F:25])=[CH:18][CH:17]=3)[N:12]=2)=[CH:7][CH:6]=1)=[N+]=[N-]>C(OCC)(=O)C.[Pd]>[F:29][C:23]([F:28])([O:22][C:19]1[CH:20]=[CH:21][C:16]([N:13]2[CH:14]=[N:15][C:11]([C:8]3[CH:9]=[CH:10][C:5]([CH2:4][NH2:1])=[CH:6][CH:7]=3)=[N:12]2)=[CH:17][CH:18]=1)[C:24]([F:27])([F:26])[F:25]

Participants

4

Reactant 1

HCID 1186751993-(4-(azidomethyl)phenyl)-1-(4-(perfluoroethoxy)phenyl)-1H-1,2,4-triazole

Product 1

HCID 118675081(4-(1-(4-(perfluoroethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)methanamineYield 98.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To 3-(4-(azidomethyl)phenyl)-1-(4-(perfluoroethoxy)phenyl)-1H-1,2,4-triazole (0.015 g, 0.037 mmol) in ethyl acetate (10 mL) was added palladium on carbon (10 wt %, 0.010 g, 0.037 mmol). The mixture was stirred under a hydrogen atmosphere (balloon) for 12 hours. The mixture was purged with nitrogen, filtered, and concentrated to provide the title compound as a white solid (0.014 g, 85%): 1H NMR (400 MHz, CDCl3) δ 8.56 (s, 1H), 8.12 (d, J=8.2 Hz, 2H), 7.80 (d, J=9.1 Hz, 2H), 7.39 (d, J=9.1 Hz, 4H), 3.87 (s, 2H), 2.42 (s, 2H); 19F NMR (376 MHz, CDCl3) δ −85.90, −87.86; ESIMS m/z 385 ([M+H]+).

Workup

  1. customThe mixture was purged with nitrogen
  2. filtrationfiltered
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-1eca9797e29f4c5d91bea594a0256288
Source dataset
uspto-grants-2016_09
Patent number
US09445594B2

Reaction notes

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