HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium Carbonate → (E)-3-{1-[4'-(2-Morpholin-4-yl-ethyl)-biphenyl-3-sulfonyl]-1H-pyrrol-3-yl}-N-(tetrahydro-pyran-2-yloxy)-acrylamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 4-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenethyl)morpholine | HCID 4439286 | — |
| Reactant | (E)-3-[1-(3-Bromo-benzenesulfonyl)-1H-pyrrol-3-yl]-N-(tetrahydro-pyran-2-yloxy)-acrylamide | HCID 86621698 | — |
| Solvent | 1,2-Dimethoxyethane | HCID 8071 | — |
| Product | (E)-3-{1-[4'-(2-Morpholin-4-yl-ethyl)-biphenyl-3-sulfonyl]-1H-pyrrol-3-yl}-N-(tetrahydro-pyran-2-yloxy)-acrylamide | HCID 86621697 | 85.8% |
Reaction Steps
(E)-3-[1-(3-Bromo-benzenesulfonyl)-1H-pyrrol-3-yl]-N-(tetrahydro-pyran-2-yloxy)-acrylamide (7.60 g) and 4-{2-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-ethyl}-morpholin (8.00 g) are dissolved in DME (300 mL). (Ph3P)3PdCl2 (2.40 g) and a 2M Na2CO3-solution (25 mL) are added and the mixture is heated 5 h to reflux temperature under an inert gas atmosphere. The reaction mixture is filtered and evaporated. After addition of a NaHCO3-solution and ethyl acetate, the organic phase is dried and evaporated. The crude product is purified by silica gel flash chromatography. 8.1 g of the title compound are obtained.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08815855B2 |
| Source dataset | uspto-grants-2014_08 |
| ORD ID | ord-81565e84454f4d87b54ee4e9e865e91a |
| Source note | uspto-grants-2014_08 |