Diazomethane → 4-Nitro-7-cyclopropyl-5-fluoro-1-isobutyl-2-(2-diethylphosphono-5-furanyl)benzimidazole

HRID 898101

Reaction equation

HRID 898101 reaction equation
[N+:1]([C:4]1[C:12]2[N:11]=[C:10]([C:13]3[O:17][C:16]([P:18]([O:23][CH2:24][CH3:25])([O:20][CH2:21][CH3:22])=[O:19])=[CH:15][CH:14]=3)[N:9]([CH2:26][CH:27]([CH3:29])[CH3:28])[C:8]=2[C:7]([CH:30]=[CH2:31])=[CH:6][C:5]=1[F:32])([O-:3])=[O:2].[N+](=[CH2:35])=[N-]>CCOCC.CC([O-])=O.CC([O-])=O.[Pd+2]>[N+:1]([C:4]1[C:12]2[N:11]=[C:10]([C:13]3[O:17][C:16]([P:18]([O:23][CH2:24][CH3:25])([O:20][CH2:21][CH3:22])=[O:19])=[CH:15][CH:14]=3)[N:9]([CH2:26][CH:27]([CH3:28])[CH3:29])[C:8]=2[C:7]([CH:30]2[CH2:35][CH2:31]2)=[CH:6][C:5]=1[F:32])([O-:3])=[O:2]

Participants

5

Reactant 2

HCID 9550DiazomethaneHCID 544096674-Nitro-7-vinyl-5-fluoro-1-isobutyl-2-(2-diethylphosphono-5-furanyl)benzimidazole

Product 1

HCID 539815924-Nitro-7-cyclopropyl-5-fluoro-1-isobutyl-2-(2-diethylphosphono-5-furanyl)benzimidazole

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 3283Diethyl EtherSolvent2×

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.

Workup

  1. customwas removed

Sources & evidence

ORD record
ord-2f23dc7ecd7945cfa67146ac4678a6ec
Source dataset
uspto-grants-2008_04
Patent number
US07351399B2

Linked notes

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