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

HRID 2243123Notes

Reaction equation

HRID 2243123 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-7a1e7b911969423bb008379880fc4ad4
Source dataset
uspto-grants-2010_03
Patent number
US07674813B2

Reaction notes

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