Sodium Iodide → 2-Methyl-2-(3-nitro-phenyl)-propionic acid 2-(2-isopropyl-imidazol-1-yl)-ethyl ester

HRID 1910797Notes

Reaction equation

Br[CH2:2][CH2:3][O:4][C:5](=[O:18])[C:6]([CH3:17])([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([N+:14]([O-:16])=[O:15])[CH:9]=1)[CH3:7].[I-].[Na+].[CH:21]([C:24]1[NH:25][CH:26]=[CH:27][N:28]=1)([CH3:23])[CH3:22].C(N(CC)CC)C>CN(C=O)C.O>[CH:21]([C:24]1[N:25]([CH2:2][CH2:3][O:4][C:5](=[O:18])[C:6]([CH3:17])([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([N+:14]([O-:16])=[O:15])[CH:9]=2)[CH3:7])[CH:26]=[CH:27][N:28]=1)([CH3:23])[CH3:22]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 2-methyl-2-(3-nitro-phenyl)-propionic acid 2-bromo-ethyl ester (1.5 g, 4.74 mmol) in DMF (8 mL) was added sodium iodide (0.73 g, 4.87 mmol) and heated at 100° C. for 1 h. 2-Isopropyl-imidazole (2.15 g, 19.5 mmol) and triethylamine (2 mL, 14.6 mmol) were added and then refluxed for 4 h. The reaction was diluted with water and extracted with DCM. The organic layer was washed thoroughly with water, dried over sodium sulfate and evaporated to obtain crude compound. Purification by column chromatography on silica gel (60-120 mesh), eluting with 30% ethyl acetate/hexane gave 2-methyl-2-(3-nitro-phenyl)-propionic acid 2-(2-isopropyl-imidazol-1-yl)-ethyl ester (320 mg, 20%) as a solid.

Workup

temperaturerefluxed for 4 h
extractionextracted with DCM
washThe organic layer was washed thoroughly with water
dry with materialdried over sodium sulfate
customevaporated
customto obtain crude compound
customPurification by column chromatography on silica gel (60-120 mesh)
washeluting with 30% ethyl acetate/hexane

Sources & evidence

ORD record: ord-05572f485ea442eeb386709dadd67828
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08604029B2

Reaction notes

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