HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium Carbonate → 6-Nitro-5-vinyl-indan-1-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | Dibutyl Vinylboronate (stabilized with Phenothiazine) | HCID 236543 | — |
| Reactant | 5-bromo-6-nitro-2,3-dihydro-1H-inden-1-one | HCID 53485149 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Oxolane--water (1/1) | HCID 21881883 | — |
| Product | 6-Nitro-5-vinyl-indan-1-one | HCID 57618480 | 79% |
Reaction Steps
A solution of 5-bromo-6-nitro-indan-1-one (58 mg, 0.23 mmol), (J. Med. Chem., 2003, 46, 399-408), vinylboronic acid dibutyl ester (74 μL, 0.34 mmol), Pd(PPh3)2Cl2 (7.8 mg, 0.0011 mmol), and Na2CO3 (167 mg, 1.57 mmol) in 4:1 THF/H2O (1.4 mL/360 μL) was heated to 80° C. overnight. The crude reaction was filtered over Celite and extracted with EtOAC. The organic phase was dried (MgSO4), filtered, and concentrated. The crude material was chromatographed (SiO2) to afford 36 mg (79%) of 6-Nitro-5-vinyl-indan-1-one; LC/MS calculated for [M+H]+ C11H9NO2: 204.1, found: 204.1.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08153671B2 |
| Source dataset | uspto-grants-2012_04 |
| ORD ID | ord-1e8c2994e86a498d92cf684018961c13 |
| Source note | uspto-grants-2012_04 |