HuagongsheHuagongshe Chemistry Print Report · For research reference only
Cesium fluoride → Methyl 3-formyl-1-(3-(naphthalen-1-yloxy)propyl)-4-o-tolyl-1h-indole-2-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Cesium fluoride | HCID 25953 | — |
| Reactant | 2-Methylphenyl boronic acid | HCID 2733267 | — |
| Reactant | Tri-tert-butylphosphine tetrafluoroborate | HCID 2734635 | — |
| Reactant | Methyl 4-bromo-3-formyl-1-[3-(1-naphthalenyloxy)propyl]-1H-indole-2-carboxylate | HCID 87353272 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | Methyl 3-formyl-1-(3-(naphthalen-1-yloxy)propyl)-4-o-tolyl-1h-indole-2-carboxylate | HCID 87353147 | — |
Reaction Steps
To a mixture of EXAMPLE 107B (0.5 g) and o-tolylboronic acid (175 mg) in tetrahydrofuran (5 ml) was added tris(dibenzylideneacetone)dipalladium(0) (25 mg), tri-t-butyl-phosphonium tetrafluoroborate (16 mg) and CsF (489 mg). The mixture was purged with Argon and stirred at room temperature for 24 hours. The mixture was diluted with ethyl acetate (200 mL) and washed with water and brine and dried over Na2SO4. After filtration, concentration of the solvent and column purification (5% ethyl acetate in hexane) provided EXAMPLE 107C.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08853209B2 |
| Source dataset | uspto-grants-2014_10 |
| ORD ID | ord-8096cc126e8b4097a8fda770ff4a741a |
| Source note | uspto-grants-2014_10 |