1-[4-(2-Azidoethyl)phenyl]-3,5-dimethyl-4-phenyl-1H-pyrazole → 2-[4-(3,5-Dimethyl-4-phenyl-1H-pyrazol-1-yl)phenyl]ethylamine

HRID 891080Notes

Reaction equation

HRID 891080 reaction equation
[N:1]([CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([N:12]2[C:16]([CH3:17])=[C:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:14]([CH3:24])=[N:13]2)=[CH:8][CH:7]=1)=[N+]=[N-]>CO.[Pd].CC([O-])=O.CC([O-])=O.[Pb+2]>[CH3:24][C:14]1[C:15]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)=[C:16]([CH3:17])[N:12]([C:9]2[CH:8]=[CH:7][C:6]([CH2:5][CH2:4][NH2:1])=[CH:11][CH:10]=2)[N:13]=1

Participants

4

Reactant 1

HCID 222445571-[4-(2-Azidoethyl)phenyl]-3,5-dimethyl-4-phenyl-1H-pyrazole

Product 1

HCID 222446652-[4-(3,5-Dimethyl-4-phenyl-1H-pyrazol-1-yl)phenyl]ethylamineYield 92%

Reagents, catalysts & solvents 2

HCID 131709914Lindlars catalystCatalystHCID 887MethanolSolvent

Procedure

To a solution of 1-[4-(2-azidoethyl)phenyl]-3,5-dimethyl-4-phenyl-1H-pyrazole (step 2, 196 mg, 0.62 mmol) in methanol (10 mL) was added Lindlar catalyst (100 mg). The resulting mixture was stirred for 5 h under hydrogen atmosphere. The mixture was filtered through a pad of Celite and the filtrate was concentrated to give 166 mg (92%) of the title compound as colorless oil: MS (ESI) m/z 292 [M+H]+, 1H-NMR (CDCl3) δ 7.47-7.39 (4H, m), 7.34-7.29 (5H, m), 3.01 (2H, t, J=6.8 Hz), 2.81 (2H, t, J=6.8 Hz), 2.34 (3H, s), 2.30 (3H, s).

Workup

  1. filtrationThe mixture was filtered through a pad of Celite
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-ba43088f8a064e0581bfbc05218a4c20
Source dataset
uspto-grants-2006_02
Patent number
US07001917B2

Reaction notes

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