HuagongsheHuagongshe Chemistry Print Report · For research reference only
Phenylboronic Acid → 7-methyl-6-phenyl-1H-indole-2,3-dione
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Phenylboronic Acid | HCID 66827 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | 6-Bromo-7-methyl-1H-indole-2,3-dione | HCID 11230188 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | 1,2-Dimethoxyethane | HCID 8071 | — |
| Product | 7-methyl-6-phenyl-1H-indole-2,3-dione | HCID 11368378 | 55.5% |
Reaction Steps
6-Bromo-7-methyl-1H-indole-2,3-dione (100 mg, 0.38 mmol) and phenylboronic acid (53 mg, 1.1 eq) were dissolved in 10 mL DME. Pd(PPh3)4 (22 mg, 0.05 eq) were added followed by NaHCO3 (65 mg, 2.0 eq) dissolved in 10 mL water. The mixture was refluxed for 2.5 hr and the organic solvent was removed by evaporation. The mixture was extracted with ethyl acetate and the combined organic layers were dried over Na2SO4 and purified by SiO2 chromatography to give the title compound (50 mg, 51%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07579313B2 |
| Source dataset | uspto-grants-2009_08 |
| ORD ID | ord-535c3c60a3474bf8b77cbfb99427d749 |
| Source note | uspto-grants-2009_08 |