HuagongsheHuagongshe Chemistry Print Report · For research reference only
Cesium fluoride → ethyl 3-(3-hydroxypropyl)-7-(2-methoxyphenyl)-1H-indole-2-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Cesium fluoride | HCID 25953 | — |
| Reactant | 2-Methoxyphenylboronic acid | HCID 2733958 | — |
| Reactant | Tri-t-butylphosphine fluoroborate | HCID 44558591 | — |
| Reactant | ethyl 7-bromo-3-(3-hydroxypropyl)-1H-indole-2-carboxylate | HCID 68943187 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | ethyl 3-(3-hydroxypropyl)-7-(2-methoxyphenyl)-1H-indole-2-carboxylate | HCID 68940496 | — |
Reaction Steps
A mixture of EXAMPLE 1B (456 mg) and 2-methoxyphenylboronic acid (182.4 mg) in THF (10 mL), tris(dibenzylideneacetone)dipalladium(0) (46 mg), tri-tert-butylphosphine tetrafluoroborate (15 mg) and CsF (456 mg) was stirred at ambient temperature, diluted with ethyl acetate (200 mL), washed with water and brine, and dried (Na2SO4), filtered and concentrated. The concentrate was purified by flash column chromatography on silica gel with 20% ethyl acetate in hexanes.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09359296B2 |
| Source dataset | uspto-grants-2016_06 |
| ORD ID | ord-453d3d5134ad4186a962777432804195 |
| Source note | uspto-grants-2016_06 |