HuagongsheHuagongshe Chemistry Print Report · For research reference only
6-Bromo-2-(4-methoxy-benzyl)-3,4-dihydro-2H-isoquinolin-1-one → [2-(4-Methoxy-benzyl)-1-oxo-1,2,3,4-tetrahydro-isoquinolin-6-yl]-acetic Acid Tert-Butyl Ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 6-Bromo-2-(4-methoxy-benzyl)-3,4-dihydro-2H-isoquinolin-1-one | HCID 59216481 | — |
| Reactant | HCID 178451183 | HCID 178451183 | — |
| Catalyst | (1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladium | HCID 6505921 | — |
| Catalyst | Ditert-butyl(cyclopenta-2,4-dien-1-yl)phosphane;iron(2+);(2,3,4,5-tetraphenylcyclopenta-1,4-dien-1-yl)benzene | HCID 129828017 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | [2-(4-Methoxy-benzyl)-1-oxo-1,2,3,4-tetrahydro-isoquinolin-6-yl]-acetic Acid Tert-Butyl Ester | HCID 59216409 | 95.6% |
Reaction Steps
6-Bromo-2-(4-methoxy-benzyl)-3,4-dihydro-2H-isoquinolin-1-one(1.9 g, 5.5 mmole), Q-phos (0.0632 g, 0.11 mmole) and Pd(dba)2 (0.0781 g, 0.11 mmole) in 10 ml THF were added to 2-tert-butoxy-2-oxoethylzinc chloride 15 ml (0.55 M) under argon. The reaction mixture was stirred at room temperature for 16 hours. Next a third of the initial amount of Q-phos, Pd(dba)2 and zinc enolate were added and the mixture heated for 1 hour at 70° C. to bring the reaction to completion. The desired product (2 g ; 95.6% yield) was isolated by flash chromatography using silica gel column chromatography with 10%-40% ethylacetate in hexane as eluent.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08299077B2 |
| Source dataset | uspto-grants-2012_10 |
| ORD ID | ord-a68ec2e177f54547a2f2903dcff2db43 |
| Source note | uspto-grants-2012_10 |