HuagongsheHuagongshe Chemistry Print Report · For research reference only
Methylamine → N2-(2-chloro-4-(methylcarbamoyl)phenyl)-N2,N8-dimethyl-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine-2,8-dicarboxamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Methylamine | HCID 6329 | — |
| Reactant | Tetrahydrofuran | HCID 8028 | — |
| Reactant | 1,8-Diazabicyclo(5.4.0)undec-7-ene | HCID 81184 | — |
| Reactant | 8-bromo-N-(2-chloro-4-(methylcarbamoyl)phenyl)-N-methyl-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine-2-carboxamide | HCID 57900373 | — |
| Catalyst | Molybdenum carbonyl (Mo(CO)6) | HCID 98885 | — |
| Catalyst | trans-Bis(acetato)bis[2-[bis(2-methylphenyl)phosphino]benzyl]dipalladium(II) | HCID 11104995 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | N2-(2-chloro-4-(methylcarbamoyl)phenyl)-N2,N8-dimethyl-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine-2,8-dicarboxamide | HCID 56683543 | — |
Reaction Steps
To a solution containing 8-bromo-N-(2-chloro-4-(methylcarbamoyl)phenyl)-N-methyl-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine-2-carboxamide and methylamine in tetrahydrofuran was added molybdenumhexacarbonyl, trans-di(mu-acetato)bis[o-(di-o-tolylphosphino)benzyl]dipalladium (II). Then 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) was added and capped quickly to prevent CO gas from escaping. The reaction mixture was heated in a microwave, then diluted with EtOAc then filtered thru celite. The combined organics were dried (Na2SO4), filtered and concentrated. The crude was submitted for RP HPLC to give 179. MS: (ESI+) 484.1
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08846762B2 |
| Source dataset | uspto-grants-2014_09 |
| ORD ID | ord-dd7b253239a942cca41d8147b51f8bfd |
| Source note | uspto-grants-2014_09 |