HuagongsheHuagongshe Chemistry Print Report · For research reference only
Bromoethene → 3-(2-Methyl-9,10-dihydro-1-oxa-3-aza-benzo[f]azulen-4-ylidenemethyl)-phenol
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Bromoethene | HCID 11641 | — |
| Reactant | (3-hydroxyphenyl)boronic Acid | HCID 2734359 | — |
| Reactant | 2-Methyl-9,10-dihydro-benzo[5,6]cyclohepta[1,2-d]oxazol-4-one | HCID 12200374 | — |
| Product | 3-(2-Methyl-9,10-dihydro-1-oxa-3-aza-benzo[f]azulen-4-ylidenemethyl)-phenol | HCID 68935026 | — |
Reaction Steps
Prepare the corresponding ketone (2-methyl-9,10-dihydro-1-oxa-3-aza-benzo[f]azulen-4-one) as described by E. E. Galantay, et al, J. Med. Chem. (17) 1316-1327 (1974) and convert to the corresponding Z-isomer of the vinyl bromide using procedures essentially as described in Preparations 23 and 24. Then, following procedures essentially as described in Example 219, combine the ketone with 3-hydroxyphenyl boronic acid (207 mg, 1.5 mmmol). Purify the crude product using column chromatography (15% EtOAc/hexane to 30% EtOAc/hexane) to give 26 mg title compound, MS (ES) 304 (M+1). HPLC shows 93% purity at t=2.48 min.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07411072B2 |
| Source dataset | uspto-grants-2008_08 |
| ORD ID | ord-d1beac0382e94efbbb63a4a0ab38495b |
| Source note | uspto-grants-2008_08 |