HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
4-(1H-imidazol-1-yl)aniline → (5-Bromo-imidazo[1,2-a]pyrazin-8-yl)-(4-imidazol-1-yl-phenyl)-amine
Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|---|---|---|
| Edukt | 4-(1H-imidazol-1-yl)aniline | HCID 320165 | — |
| Edukt | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | HCID 636044 | — |
| Edukt | Sodium t-butoxide | HCID 23676156 | — |
| Edukt | N-(4-Hydroxybenzyl)-4-[5-(1H-pyrazol-4-yl)imidazo[1,2-a]pyrazin-8-ylamino]benzamide | HCID 24857547 | — |
| Edukt | 5,8-Dibromoimidazo[1,2-a]pyrazine | HCID 53485949 | — |
| Katalysator | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Lösungsmittel | Toluene | HCID 1140 | — |
| Produkt | (5-Bromo-imidazo[1,2-a]pyrazin-8-yl)-(4-imidazol-1-yl-phenyl)-amine | HCID 59023113 | — |
Reaktionsschritte
In the same way as described for Compound 90, step 1, using 5,8-dibromoimidazo[1,2-a]pyrazine (203.8 mg, 0.736 mmol), 4-imidazol-1-yl-phenylamine (117.7 g, 0.739 mmol), NaOtBu (99 mg, 1.03 mmol), Pd2(dba)3 (27.0 mg, 0.0295 mmol), Xantphos (34.1 mg, 0.0589 mmol) and toluene (10 mL). The crude material is purified by Isolute FlashSilicaII cartridge chromatography eluting with 99:1 DCM:NH3 (7M in MeOH), followed by 97:3 DCM/NH3 (7M in MeOH). The title compound is isolated, after a second column chromatography purification using a 5:5:1 mixture EtOAc-petroleum ether-MeOH, as a yellow solid (104 mg, 40%).
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patentnummer | US08173656B2 |
| Quelldatensatz | uspto-grants-2012_05 |
| ORD ID | ord-014a48bc794a434eaa6d96046db06f60 |
| Quellennotiz | uspto-grants-2012_05 |