2-Bromo-5-bromomethylpyridine → 5-(4-Cyanobenzyl)-1-(2-bromopyrid-5-ylmethyl)imidazole

HRID 365467Notizen

Reaktionsgleichung

C([N:20]1[CH:24]=[C:23]([CH2:25][C:26]2[CH:31]=[CH:30][C:29]([C:32]#[N:33])=[CH:28][CH:27]=2)[N:22]=[CH:21]1)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Br:34][C:35]1[CH:40]=[CH:39][C:38]([CH2:41]Br)=[CH:37][N:36]=1>CN(C=O)C>[C:32]([C:29]1[CH:28]=[CH:27][C:26]([CH2:25][C:23]2[N:22]([CH2:41][C:38]3[CH:39]=[CH:40][C:35]([Br:34])=[N:36][CH:37]=3)[CH:21]=[N:20][CH:24]=2)=[CH:31][CH:30]=1)#[N:33]

Komponenten

Reaktionsbedingungen

Temperatur: 100 °C

Versuchsvorschrift

To a flask was charged 1-trityl -4-p-cyanobenzyl imidazole (2.77 mmol, 1.18 g) from Step 1 and 2-bromo-5-bromomethyl pyridine (2.77 mmol, 0.67 g) from Step 2 in DMF (10 mL) and the mixture heated at 100° C. for 6 hr. The DMF was then removed in vacuo and the residue was triturated with ethyl ether. The ethyl ether was then decanted off and replaced with methanol (20 mL). This solution was then refluxed for 4 hr, cooled to ambient temperature and purified on a C18 preperative hplc column to provide the title compound. High resolution FAB-MS: calc; 353.040183 found; 353.040183. 1H-NMR (CD3OD): 4.2 ppm (s, 2H); 5.4 ppm (s, 2H); 7.2 and 7.6 ppm (d, 2H); 8.1 ppm (s, 1H); 9.1 ppm (s, 1H).

Aufarbeitung

customThe DMF was then removed in vacuo
customthe residue was triturated with ethyl ether
customThe ethyl ether was then decanted off
temperatureThis solution was then refluxed for 4 hr
temperaturecooled to ambient temperature
custompurified on a C18 preperative hplc column

Quellen und Nachweise

ORD-Eintrag: ord-97e920e5ef3f44a5afc1d1811b1613ca
Quelldatensatz: uspto-grants-2000_10
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06127390

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