1,8-Diazabicyclo(5.4.0)undec-7-ene → 4-(Azidomethyl)-1-[4-(methylsulfonyl)phenyl]-1H-pyrazole

HRID 2060082Notes

Reaction equation

HRID 2060082 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH:15]=[C:14]([CH2:16]O)[CH:13]=[N:12]2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].C1(P([N:32]=[N+:33]=[N-:34])(C2C=CC=CC=2)=O)C=CC=CC=1.N12CCCN=C1CCCCC2>C1COCC1>[N:32]([CH2:16][C:14]1[CH:13]=[N:12][N:11]([C:8]2[CH:9]=[CH:10][C:5]([S:2]([CH3:1])(=[O:4])=[O:3])=[CH:6][CH:7]=2)[CH:15]=1)=[N+:33]=[N-:34]

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 199401P,P-Diphenylphosphinic azideHCID 59406331{1-[4-(Methanesulfonyl)phenyl]-1H-pyrazol-4-yl}methanol

Product 1

HCID 594064244-(Azidomethyl)-1-[4-(methylsulfonyl)phenyl]-1H-pyrazoleYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of [1-(4-methanesulfonyl-phenyl)-1H-pyrazol-4-yl]-methanol (1.80 g, 7.12 mmol, 1.00 equiv) and diphenylphosphoryl azide (2.35 g, 8.54 mmol, 1.2 equiv) in THF (15 mL) at rt was added 1,8-diazabicyclo[5.4.0]undec-7-ene (1.3 g, 8.54 mmol, 1.2 equiv). The resulting solution was stirred overnight, concentrated and chromatographically purified (15% ethyl acetate in hexanes) to give 4-azidomethyl-1-(4-methanesulfonyl-phenyl)-1H-pyrazole (1.90 g, 97%). LCMS: (MH)+=278.0 (1.45 min).

Workup

  1. concentrationconcentrated
  2. customchromatographically purified (15% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-770d329f1f9043cdbb54e6da9ede2d61
Source dataset
uspto-grants-2012_10
Patent number
US08278337B2

Reaction notes

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