Dimethylformamide → HCID 18437822, compound

HRID 457402Notes

Reaction equation

COCC[N:5]1[C:9]([CH:10]([O:12][CH3:13])[CH3:11])=[C:8]([Cl:14])[N:7](Cl)[CH:6]1[C:16]1[C:21]([CH2:22][CH3:23])=[CH:20][CH:19]=[CH:18][C:17]=1[CH2:24][CH3:25].[Li]CCCC.CN([CH:34]=[O:35])C>C1COCC1>[CH2:24]([C:17]1[CH:18]=[CH:19][CH:20]=[C:21]([CH2:22][CH3:23])[C:16]=1[C:6]1[N:7]([CH:34]=[O:35])[C:8]([Cl:14])=[C:9]([CH:10]([O:12][CH3:13])[CH3:11])[N:5]=1)[CH3:25]

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of N-methoxyethyl 2-(2,6-diethylphenyl)-1-methoxyethyl-3,4-dichloroimidazole (3.27 g, 10 mmol.) in anhydrous THF is added n-BuLi (1.6M in hexane) (9.4 ml, 15 mmol) dropwise at −78° C. After the reaction mixture is stirred at −78° C. for 2 h, anhydrous DMF (3 equiv.) is added in one portion. The mixture is stirred at −78° C. for 30 min, then allowed to warm to room temperature slowly. The reaction mixture is quenched with water and extracted with ethyl acetate, dried over MgSO4, filtered, concentrated in vacuo and purified by chromatography on silica gel to give 2-(2,6-diethylphenyl)-1-methoxyethyl-4-chloro-imidazole-3-carboxaldehyde. This material is used to make various compounds of Formula I as depicted in Scheme 10 and further illustrated in Examples 4–9 and related examples.

Workup

stirringThe mixture is stirred at −78° C. for 30 min
temperatureto warm to room temperature slowly
customThe reaction mixture is quenched with water
extractionextracted with ethyl acetate
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated in vacuo
custompurified by chromatography on silica gel

Sources & evidence

ORD record: ord-71bc900842fd496eb9e4eee85e5b276c
Source dataset: uspto-grants-2007_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07186734B2

Reaction notes

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