HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium Sulfate → (E)-3-{1-[4-(1-methyl-1H-indol-5-yl)-benzenesulfonyl]-1H-pyrrol-3-yl}-N-(tetrahydro-pyran-2-yloxy)-acrylamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium Sulfate | HCID 24436 | — |
| Reactant | 1-Methyl-1H-indole-5-boronic acid | HCID 2759867 | — |
| Reactant | (E)-3-[1-(4-Bromo-benzenesulfonyl)-1H-pyrrol-3-yl]-N-(tetrahydro-pyran-2-yloxy)-acrylamide | HCID 86621691 | — |
| Catalyst | Dichlorobis(triphenylphosphine)palladium | HCID 6102075 | — |
| Solvent | 1,2-Dimethoxyethane | HCID 8071 | — |
| Product | (E)-3-{1-[4-(1-methyl-1H-indol-5-yl)-benzenesulfonyl]-1H-pyrrol-3-yl}-N-(tetrahydro-pyran-2-yloxy)-acrylamide | HCID 86621684 | — |
Reaction Steps
A mixture of 0.4 g (E)-3-[1-(4-Bromo-benzenesulfonyl)-1H-pyrrol-3-yl]-N-(tetrahydro-pyran-2-yloxy)-acrylamide, 0.231 g N-Methylindol-5-boronic acid and 14 ml dimethoxyethane is slightly heated and to this mixture are added bis(triphenylphosphine)palladium(II)chloride and 1.5 ml of a 2M aqueous sodium sulfate solution. This mixture is heated to reflux temperature under an inert gas atmosphere overnight. After cooling the mixture is filtered, evaporated and the residue is partitioned between ethyl acetate and a 5% aqueous solution of sodium bicarbonate. The organic phase is dried and evaporated and the residue is purified by silica gel flash chromatography.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08815855B2 |
| Source dataset | uspto-grants-2014_08 |
| ORD ID | ord-376ee4baf3c74b70bfbc6d38e36617f4 |
| Source note | uspto-grants-2014_08 |