HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
3-Methoxyaniline → N-(3-Methoxyphenyl)-4-methyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzamide
Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|---|---|---|
| Edukt | 3-Methoxyaniline | HCID 10824 | — |
| Edukt | Diisopropylethylamine | HCID 81531 | — |
| Edukt | Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 9886157 | — |
| Edukt | 4-Methyl-3-(tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid | HCID 16086086 | — |
| Lösungsmittel | Dimethylformamide | HCID 6228 | — |
| Produkt | N-(3-Methoxyphenyl)-4-methyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzamide | HCID 59791522 | 73,5% |
Reaktionsschritte
4-Methyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid (Intermediate 4) (2 g) was dissolved in DMF (20 ml). To this was added 3-methoxyaniline (0.985 g), DIPEA (4 ml) and HATU (3.05 g). The mixture was stirred for 18 h at room temp. The solvent was removed under vacuum and the residue was partitioned between ethyl acetate (250 ml) and water (50 ml). The organic layer was dried (magnesium sulphate) concentrated under vacuum and purified using a silica Biotage cartridge (90 g) eluting with 1:4 ethyl acetate/cyclohexane to give the title compound as a white solid (2.06 g).
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patentnummer | US07642276B2 |
| Quelldatensatz | uspto-grants-2010_01 |
| ORD ID | ord-51bcc981ae6044e8889489b1673e0f57 |
| Quellennotiz | uspto-grants-2010_01 |