Reaction #985283

ord-2f23dc7ecd7945cfa67146ac4678a6ec

Reaction equation

C=[N+]=[N-]
diazomethane
C=Cc1cc(F)c([N+](=O)[O-])c2nc(-c3ccc(P(=O)(OCC)OCC)o3)n(CC(C)C)c12
4-nitro-7-vinyl-5-fluoro-1-isobutyl-2-(2-diethylphosphono-5-furanyl)benzimidazole
→
CCOP(=O)(OCC)c1ccc(-c2nc3c([N+](=O)[O-])c(F)cc(C4CC4)c3n2CC(C)C)o1
4-nitro-7-cyclopropyl-5-fluoro-1-isobutyl-2-(2-diethylphosphono-5-furanyl)benzimidazole

Reactants

C=[N+]=[N-]
diazomethane
C=Cc1cc(F)c([N+](=O)[O-])c2nc(-c3ccc(P(=O)(OCC)OCC)o3)n(CC(C)C)c12
4-nitro-7-vinyl-5-fluoro-1-isobutyl-2-(2-diethylphosphono-5-furanyl)benzimidazole

Reagents

CC(=O)[O-].CC(=O)[O-].[Pd+2]
Pd(OAc)2

Solvents

CCOCC
ether
CCOCC
ether

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Otherwas removed

Procedure

To a suspension of 1.0 mmol of 4-nitro-7-vinyl-5-fluoro-1-isobutyl-2-(2-diethylphosphono-5-furanyl)benzimidazole and 0.1 mmol of Pd(OAc)2 in 8 mL of ether was added an ether solution of diazomethane(generated from 3.0 g of 1-methyl-3-nitro-1-nitrosoguanidine) at 0° C. After stirring at rt 20 h. solvent was removed and the residue was subjected to chromatography to give 4-nitro-7-cyclopropyl-5-fluoro-1-isobutyl-2-(2-diethylphosphono-5-furanyl)benzimidazole.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07351399B2uspto-grants-2008_04