HuagongsheHuagongshe Chemistry Print Report · For research reference only
Tri-o-tolylphosphine → (E)-N-[1-(2-dimethylaminoethyl)-1H-indol-3-ylmethyl]-N-methyl-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Tri-o-tolylphosphine | HCID 80271 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 6-Bromo-3,4-dihydro-1,8-naphthyridin-2(1H)-one | HCID 11096325 | — |
| Reactant | N-[1-(2-dimethylaminoethyl)-1H-indol-3-ylmethyl]-N-methyl-acrylamide | HCID 66905455 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | Propionitrile | HCID 7854 | — |
| Product | (E)-N-[1-(2-dimethylaminoethyl)-1H-indol-3-ylmethyl]-N-methyl-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylamide | HCID 10252195 | — |
Reaction Steps
A solution of 6-bromo-3,4-dihydro-1H-1,8-naphthyridin-2-one (0.61 g, 2.70 mmole), N-[1-(2-dimethylaminoethyl)-1H-indol-3-ylmethyl]-N-methyl-acrylamide (1.00 g, 3.50 mmole), Pd(OAc)2 (0.08 g, 0.35 mmole), tri-ortho-tolylphosphine (0.21 g, 0.70 mmole), and diisopropylethylamine (0.91 mL, 5.25 mmole) in propionitrile (70 mL) was deoxygenated, then was and heated to reflux under a N2 overnight. The dark mixture was filtered through a pad of celite®, and the filter pad was rinsed with acetonitrile (250 mL).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08153652B2 |
| Source dataset | uspto-grants-2012_04 |
| ORD ID | ord-1e21122d16134bf0b159b234e3f5bc7e |
| Source note | uspto-grants-2012_04 |