HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium Carbonate → (E)-3-{1-[4'-(3-Morpholin-4-yl-propoxy)-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-(3-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)propyl)morpholine | HCID 4649072 | — |
| Reactant | HCID 86621698 | HCID 86621698 | — |
| Solvent | 1,2-Dimethoxyethane | HCID 8071 | — |
| Product | (E)-3-{1-[4'-(3-Morpholin-4-yl-propoxy)-biphenyl-3-sulfonyl]-1H-pyrrol-3-yl}-N-(tetrahydro-pyran-2-yloxy)-acrylamide | HCID 86640144 | 78.1% |
Reaction Conditions
| Temperature | 100 °C |
|---|
Reaction Steps
(E)-3-[1-(3-Bromo-benzenesulfonyl)-1H-pyrrol-3-yl]-N-(tetrahydro-pyran-2-yloxy)-acrylamide (4.6 g) and 4-{3-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenoxy]-propyl}-morpholine (3.9 g) are dissolved in DME (200 mL). Under an inert gas atmosphere are added are added (Ph3P)3PdCl2 (1.4 g) and 2M Na2CO3-solution (31 mL). The mixture is heated to 100° C. for 2 h. After filtration and extraction, the crude product from the organic phase is purified by silica gel flash chromatography. 4.7 g of the title compound are obtained as brownish oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08815855B2 |
| Source dataset | uspto-grants-2014_08 |
| ORD ID | ord-0c3a7d2f3ab5490e93a1cd915c6059e3 |
| Source note | uspto-grants-2014_08 |