Hexane → 1-[1-(4-cyanophenyl)4-(4-fluorophenyl)butyl]-1H-imidazole

HRID 1941287Notes

Reaction equation

[C:1]([C:3]1[CH:14]=[CH:13][C:6]([CH2:7][N:8]2[CH:12]=[CH:11][N:10]=[CH:9]2)=[CH:5][CH:4]=1)#[N:2].[Li]CCCC.CCCCCC.[F:26][C:27]1[CH:32]=[CH:31][C:30]([CH2:33][CH2:34][CH2:35]Br)=[CH:29][CH:28]=1.[Cl-].[NH4+]>C1COCC1>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([CH:7]([N:8]2[CH:12]=[CH:11][N:10]=[CH:9]2)[CH2:35][CH2:34][CH2:33][C:30]2[CH:31]=[CH:32][C:27]([F:26])=[CH:28][CH:29]=2)=[CH:13][CH:14]=1)#[N:2]

Participants

Conditions

Temperature: -70 °C

Procedure

1-(4-cyanobenzyl)-imidazole (1 g, 0.0054 mol) is dissolved into dry tetrahydrofuran (30 ml) and cooled to -70° C. n-BuLi in hexane (0.0054 mol) is added dropwise into the reaction mixture. After stirring for additional 30 min at -70° C. 3-(4-fluorophenyl)propyl bromide (1.5 g, 0,0069 mol) in THF (10 ml) is added to the mixture and stirring is continued for 2 hours. Then the mixture is allowed to warm to room temperature. Saturated aqueous ammonium chloride solution is added to the mixture, shaked and then the layers are separated. THF-phase is dried and evaporated to dryness. The residue is crystallized from isopropanol as hydrogen chloride salt. The filtrate is purified by flash chromatography.

Workup

additionis added dropwise into the reaction mixture
stirringstirring
waitis continued for 2 hours
temperatureto warm to room temperature
customshaked and then the layers are separated
dry with materialTHF-phase is dried
customevaporated to dryness
customThe residue is crystallized from isopropanol as hydrogen chloride salt
customThe filtrate is purified by flash chromatography

Sources & evidence

ORD record: ord-b23679e879fb45dba8749288c679f6cd
Source dataset: uspto-grants-1997_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05703109

Reaction notes

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