HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
Tetrahydrofuran → N-(3,4-Dimethoxybenzyl)-3H-benzo[d]imidazol-5-amine
Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|---|---|---|
| Edukt | Tetrahydrofuran | HCID 8028 | — |
| Edukt | Veratrylamine | HCID 79832 | — |
| Edukt | 6-Bromo-1H-benzimidazole | HCID 785299 | — |
| Edukt | Lithium Hexamethyldisilazide | HCID 2733832 | — |
| Edukt | 2-(Dicyclohexylphosphino)-2'-(dimethylamino)biphenyl | HCID 2734217 | — |
| Katalysator | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Produkt | N-(3,4-Dimethoxybenzyl)-3H-benzo[d]imidazol-5-amine | HCID 67444547 | — |
Reaktionsschritte
The compound was synthesized starting from 5-bromobenzimidazole (200 mg; 1 mmol; 1 eq.), 3,4-dimethoxybenzylamine (201 mg; 0.181 ml; 1.2 mmol; 1.2 eq.), 2-dicyclohexylphosphino-2′-(N,N-dimethylamino)biphenyl (9 mg; 0.024 mmol; 0.024 eq.; 2.4 mol %), Pd2 dba3 (9 mg; 0.01 mmol; 0.01 eq.; 1 mol %) and lithiumbis(trimethylsilyl)amide 1 M in THF (2.2 ml; 2.2 mmol; 2.2 eq.) according to method 1; Yield: 0.064 g (22.6%); MS m/z: 284.1 [M+H]+; 1H-NMR (500 MHz, DMSO d6): δ 3.69 (s, 3H); 3.71 (s, 3H); 4.17 (d, 2H, 3J=5.8 Hz); 5.96 (br s, 1H); 6.48 (br s, 1H); 6.58-6.60 (m, 1H); 6.85-6.89 (m, 2H); 6.99 (s, 1H); 7.27-7.29 (m, 1H); 7.80 (s, 1H); 11.78 (br s, 1H); HPLC (METHOD [A]): rt 8.92 min (100%)
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patentnummer | US08541596B2 |
| Quelldatensatz | uspto-grants-2013_09 |
| ORD ID | ord-900fc40b0b2a41c596b389099d73e2a8 |
| Quellennotiz | uspto-grants-2013_09 |