HCID 21866175, compound → HCID 21866317, compound

HRID 857778Notes

Reaction equation

HRID 857778 reaction equation
[N:1]1([C:6]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][C:7]=2[C:8]#[N:9])[CH:5]=[N:4][N:3]=[N:2]1>N.[Ni].O>[N:1]1([C:6]2[CH:13]=[CH:12][C:11]([C:14]([F:16])([F:17])[F:15])=[CH:10][C:7]=2[CH2:8][NH2:9])[CH:5]=[N:4][N:3]=[N:2]1

Participants

5

Reactant 1

HCID 21866175HCID 21866175, compound

Product 1

HCID 21866317HCID 21866317, compound

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 222AmmoniaSolventHCID 962WaterSolvent

Procedure

To a solution of 2-(1H-tetraazol-1-yl)-5-(trifluoromethyl)benzonitrile (166 mg, 0.69 mmol) in saturated ethanolic ammonia (12 mL) was added Raney nickel (50% slurry in water; the water was decanted and the catalyst rinsed with EtOH three times before use). The mixture was quickly degassed and purged with Ar, and was then placed under H2 atmosphere (balloon) and stirred for 16 h. The mixture was then filtered through Celite and the filter cake was rinsed thoroughly with EtOH. The filtrate was concentrated to a brown oil. Silica gel chromatography (70% EtOAc-hexanes then 5% MeOH-CHCl3) afforded the title compound as an orange-brown solid. 1H NMR (400 MHz, CDCl3): δ 9.41 (s, 1H), 7.93 (br s, 1H), 7.76 (d, J=8.0 Hz, 1H), 7.62 (d, J=8.0 Hz, 1H), 3.81 (s, 2H), 1.57 (br s, 2H). LCMS (M+H): 243.9.

Workup

  1. customthe water was decanted
  2. washthe catalyst rinsed with EtOH three times before use)
  3. customThe mixture was quickly degassed
  4. custompurged with Ar
  5. filtrationThe mixture was then filtered through Celite
  6. washthe filter cake was rinsed thoroughly with EtOH
  7. concentrationThe filtrate was concentrated to a brown oil

Sources & evidence

ORD record
ord-bc8f9dfb5134470eb7a1cdf139082551
Source dataset
uspto-grants-2006_12
Patent number
US07144899B2

Reaction notes

Loading…