Triphenylphosphine → 5-(1-azido-2-ethylbutyl)-1-[(4-methylphenyl)sulfonyl]-1H-pyrazole

HRID 748044Notes

Reaction equation

HRID 748044 reaction equation
[CH2:1]([CH:3]([CH2:21][CH3:22])[CH:4]([C:6]1[N:10]([S:11]([C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=2)(=[O:13])=[O:12])[N:9]=[CH:8][CH:7]=1)O)[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.C1(P([N:68]=[N+:69]=[N-:70])(C2C=CC=CC=2)=O)C=CC=CC=1>C1COCC1>[N:68]([CH:4]([C:6]1[N:10]([S:11]([C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=2)(=[O:13])=[O:12])[N:9]=[CH:8][CH:7]=1)[CH:3]([CH2:21][CH3:22])[CH2:1][CH3:2])=[N+:69]=[N-:70]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 199401P,P-Diphenylphosphinic azideHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 685938962-ethyl-1-{1-[(4-methylphenyl)sulfonyl]-1H-pyrazol-5-yl}butan-1-ol

Product 1

HCID 866000035-(1-azido-2-ethylbutyl)-1-[(4-methylphenyl)sulfonyl]-1H-pyrazoleYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 2-ethyl-1-{1-[(4-methylphenyl)sulfonyl]-1H-pyrazol-5-yl}butan-1-ol (0.250 g, 0.778 mmol) in THF (10 mL) at 0° C. was added triphenylphosphine (0.307 g, 1.17 mmol), diethyl azodicarboxylate (0.18 mL, 1.2 mmol), and diphenylphosphoryl azide (0.25 mL, 1.2 mmol). The reaction mixture was warmed to room temperature and stirred for 20 h. The solvent was removed in vacuo and the resulting residue was purified by column chromatography (EtOAc/hexanes, 15:85) to give 0.260 g (97%) of 5-(1-azido-2-ethylbutyl)-1-[(4-methylphenyl)sulfonyl]-1H-pyrazole with an aromatic impurity as judged by 1H NMR. This compound was used in the next step without further purification.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe resulting residue was purified by column chromatography (EtOAc/hexanes, 15:85)

Sources & evidence

ORD record
ord-65eb0e510eed4b329307347e3511d58d
Source dataset
uspto-grants-2008_07
Patent number
US07399778B2

Reaction notes

Loading…