Sodium hydride → tert-Butyl 2-[4-(2-butyl-4-chloro-5-formyl-imidazol-1-yl-methyl)phenyl]-2-cyclopentylacetate

HRID 2210563Notes

Reaction equation

[H-].[Na+].[CH2:3]([C:7]1[NH:8][C:9]([CH:13]=[O:14])=[C:10]([Cl:12])[N:11]=1)[CH2:4][CH2:5][CH3:6].Br[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([CH:23]([CH:31]2[CH2:35][CH2:34][CH2:33][CH2:32]2)[C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])=[CH:19][CH:18]=1>CN(C=O)C>[CH2:3]([C:7]1[N:8]([CH2:16][C:17]2[CH:18]=[CH:19][C:20]([CH:23]([CH:31]3[CH2:32][CH2:33][CH2:34][CH2:35]3)[C:24]([O:26][C:27]([CH3:30])([CH3:28])[CH3:29])=[O:25])=[CH:21][CH:22]=2)[C:9]([CH:13]=[O:14])=[C:10]([Cl:12])[N:11]=1)[CH2:4][CH2:5][CH3:6]

Participants

Conditions

Temperature: 0 °C

Procedure

1.6 g (0.053 mol) of sodium hydride (80% strength) are suspended in 50 ml of DMF under protective gas, 10 g (0.053 mol) of 2-butyl-5-formyl-4-chloroimidazole (preparation according to EP 324 377) are added dropwise at 0° C. in 100 ml of DMF, then the mixture is stirred for 15 min at 0° C. and 18.9 g (0.053 mol) of tert-butyl 2-(4-bromomethylphenyl)-2-cyclopentylacetate in 100 ml of DMF are added dropwise. The mixture is additionally stirred at 0° C. for 2 h, the solvent is evaporated, the residue is taken up in diethyl ether, the solid is filtered off and, after concentration, the residue is chromatographed on silica gel 60 using dichloromethane.

Workup

stirringThe mixture is additionally stirred at 0° C. for 2 h
customthe solvent is evaporated
filtrationthe solid is filtered off
concentrationafter concentration
customthe residue is chromatographed on silica gel 60 using dichloromethane

Sources & evidence

ORD record: ord-a333590660ee47f5a270f4564a4be9c7
Source dataset: uspto-grants-1995_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05459156

Reaction notes

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