HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → HCID 57860171, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 3-Bromobenzonitrile | HCID 23381 | — |
| Reactant | 2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl | HCID 11155794 | — |
| Reactant | Sodium t-butoxide | HCID 23676156 | — |
| Reactant | HCID 57860479 | HCID 57860479 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Methyl Ethyl Ketone | HCID 6569 | — |
| Product | HCID 57860171 | HCID 57860171 | 7.4% |
Reaction Steps
A solution of the compound of Example 77 (300 mg, 0.59 mmol), 3-bromobenzonitrile (143 mg, 1.2 mmol), tris(dibenzylideneacetone)dipalladium (0) (54 mg, 0.059 mmol), x-phos (56 mg, 0.12 mmol), sodium tert-butoxide (142 mg, 1.5 mmol) and triethylamine (0.082 mL, 0.59 mmol) in 2-butanone (4.0 mL) was stirred under microwave irradiation at 130° C. for 40 min. The reaction mixture was diluted with water, and extracted twice with ethyl acetate. The extract was dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by aminosilica gel chromatography (eluate; ethyl acetate/hexane=40/60-100/0) and recrystallized from ethyl acetate-hexane to give the title compound (25 mg, 7.4%) as a white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08399449B2 |
| Source dataset | uspto-grants-2013_03 |
| ORD ID | ord-ddce4c75cdc44a83a161b813f17633e0 |
| Source note | uspto-grants-2013_03 |