4-Iodo-1-tritylimidazole → (4-Cyano-3-fluorophenyl)[1-(triphenylmethyl)imidazol-4-yl]methanol

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Reaktionsgleichung

I[C:2]1[N:3]=[CH:4][N:5]([C:7]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=1.C([Mg]Br)C.[F:30][C:31]1[CH:38]=[C:37]([CH:39]=[O:40])[CH:36]=[CH:35][C:32]=1[C:33]#[N:34]>C(Cl)Cl>[F:30][C:31]1[CH:38]=[C:37]([CH:39]([OH:40])[C:2]2[N:3]=[CH:4][N:5]([C:7]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH:6]=2)[CH:36]=[CH:35][C:32]=1[C:33]#[N:34]

Komponenten

Reaktionsbedingungen

Temperatur: -78 °C

Versuchsvorschrift

To a solution of 4-iodo-1-trityl-1H-imidazole (5.00 g, 11.5 mmol) in anhydrous CH2Cl2 (30 mL) was added a 3.0M solution of ethylmagnesium bromide (6.58 mL, 19.7 mmol) with stirring under Ar. After 3 h, the reaction mixture was cooled to −78° C. and a solution of 2-fluoro-4-formyl-benzonitrile (1.70 g, 11.5 mmol) dissolved in CH2Cl2 (20 mL) was added dropwise. The reaction was allowed to warm to RT over 2 h, quenched with saturated NH4Cl solution, diluted with satd. NaHCO3 solution to pH=8.5, and extracted with CH2Cl2 (3×). The combined organic layers were dried (MgSO4), concentrated and purified using SiO2 chromatography (0-1% MeOH/CH2Cl2) to yield the title compound.

Aufarbeitung

additionwas added dropwise
temperatureto warm to RT over 2 h
customquenched with saturated NH4Cl solution
additiondiluted with satd
extractionNaHCO3 solution to pH=8.5, and extracted with CH2Cl2 (3×)
dry with materialThe combined organic layers were dried (MgSO4)
concentrationconcentrated
custompurified

Quellen und Nachweise

ORD-Eintrag: ord-44723afb7ff442e89d8c29a40697db92
Quelldatensatz: uspto-grants-2001_10
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06297239B1

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