Dimethylformamide → 4-bromo-1-trityl-1H-imidazole-2-carbaldehyde

HRID 2105000Notizen

Reaktionsgleichung

[Br:1][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.[Li]CCCC.CN([CH:34]=[O:35])C>C1COCC1>[Br:1][C:2]1[N:3]=[C:4]([CH:34]=[O:35])[N:5]([C:7]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:6]=1

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

To 4-bromo-1-trityl-1H-imidazole (2.00 g, 5.14 mmol) in 30 mL THF at 0° C., was added a solution of BuLi (1.6M in hexanes, 3.85 mL, 6.17 mmol). The mixture was stirred at 0° C. for 1.25 h, then DMF (0.80 mL, 10.3 mmol) was added. The mixture was stirred for 1 h at 0° C. and 1 h at rt, then was quenched with sat. NH4Cl. The mixture was diluted with EtOAc, washed with H2O and brine, dried (Na2SO4), filtered through a 1″ pad of SiO2 and concentrated. The crude product was purified by flash chromatography (0 to 40% EtOAc/hexanes gradient) to afford 1.24 g of Intermediate 175.1 as a colorless solid.

Aufarbeitung

stirringThe mixture was stirred for 1 h at 0° C. and 1 h at rt
customwas quenched with sat. NH4Cl
additionThe mixture was diluted with EtOAc
washwashed with H2O and brine
dry with materialdried (Na2SO4)
filtrationfiltered through a 1″ pad of SiO2
concentrationconcentrated
customThe crude product was purified by flash chromatography (0 to 40% EtOAc/hexanes gradient)

Quellen und Nachweise

ORD-Eintrag: ord-7180899fbd8c401dbffecbe179150294
Quelldatensatz: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07576098B2

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