Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 2,6-Dibromobenzaldehyde | HCID 12648641 | — |
| Reactant | HCID 59216518 | HCID 59216518 | — |
| Catalyst | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | HCID 636044 | — |
| Catalyst | (1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladium | HCID 6505921 | — |
| Product | HCID 59216385 | HCID 59216385 | 46% |
Reaction Steps
To 1.3 g (6.07 mmol) 2-methyl-2-(1-oxo-1,2,3,4-tetrahydroisoquinolin-6-yl)-propionitrile dissolved in 20 ml degassed dioxane was added 6.40 g (24.27 mmol) 2,6-dibromobenzaldehyde, 3.96 g (12.14 mmol) cesium carbonate, 70 mg (0.121 mmol) Pd(dba)2, and 105 mg (0.182 mmol) xantphos. The mixture was heated to 110° C. for 3 h, cooled to room temperature, and filtered over Celite rinsing with dioxane. The mixture was then concentrated and purified by column chromatography, eluting with ethyl acetate/hexanes to provide 1.10 g (46%) 2-[2-(3-bromo-2-formylphenyl)-1-oxo-1,2,3,4-tetrahydroisoquinolin-6-yl]-2-methylpropionitrile.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07683064B2 |
|---|
| Source dataset | uspto-grants-2010_03 |
|---|
| ORD ID | ord-cb58fc3036fc4e2d8261308043abd562 |
|---|
| Source note | uspto-grants-2010_03 |
|---|
