HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → 1-(1-Acetyl-6-benzyloxy-3-methyl-1H-indol-5-yl)-ethanone
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Tri-o-tolylphosphine | HCID 80271 | — |
| Reactant | N-(4-Acetyl-5-benzyloxy-2-bromo-phenyl)-N-allyl-acetamide | HCID 57934833 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | 1-(1-Acetyl-6-benzyloxy-3-methyl-1H-indol-5-yl)-ethanone | HCID 57934843 | 54% |
Reaction Steps
A solution of N-(4-acetyl-5-benzyloxy-2-bromo-phenyl)-N-allyl-acetamide (0.662 g, 1.65 mmol), P(o-tolyl)3 (0.028 g, 0.092 mmol) and triethylamine (0.34 ml, 2.24 mmol) in MeCN (15 ml) was flushed with nitrogen, followed by the addition of a Pd(OAc)2 (0.005 g). The reaction was microwaved for 500 sec. at 150° C. The crude mixture was diluted with EtOAc, washed with water and dried over MgSO4. Purification by column chromatography in hexane/EtOAc (1:1) afforded (0.283 g, 54%) a cream solid. LC/MS: RT=2.742 min. 322 (MH+), 344 (MNa+), 280 (MH+-Ac).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07612201B2 |
| Source dataset | uspto-grants-2009_11 |
| ORD ID | ord-df7fb2c0567241dcb0490c145ab4a670 |
| Source note | uspto-grants-2009_11 |