Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Acetate | HCID 517045 | — |
| Reactant | HCID 58044167 | HCID 58044167 | — |
| Reactant | 2-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-4-fluoro-6-(1-oxo-3,4,6,7,8,9-hexahydropyrazino[1,2-a]indol-2(1H)-yl)benzyl Acetate | HCID 58044205 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | HCID 58043743 | HCID 58043743 | 15.3% |
Reaction Steps
A sealed tube was charged with the mixture of 331a (400 mg, 1 mmol), 4-fluoro-2-(1-oxo-3,4,6,7,8,9-hexahydropyrazino[1,2-a]indol-2(1H)-yl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl acetate 210d (578 mg, 1.2 mmol), Pd(dppf)Cl2 (82 mg, 0.1 mmol), K3PO4.3H2O(760 mg, 2 mmol), and NaOAc (164 mg, 2 mmol) in CH3CN (10 mL). The system was evacuated and then refilled with N2 and the reaction mixture was heated at 110° C. for 2 h. The mixture was then cooled to room temperature and filtered. The filtrate was concentrated under reduced pressure and the resulting residue was purified by flash column chromatography eluting with 50:1 methylene chloride/methanol to afford 331b as a yellow solid (100 mg, 14%). MS: [M+H]+ 655.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08618107B2 |
|---|
| Source dataset | uspto-grants-2013_12 |
|---|
| ORD ID | ord-a7b8352c6b96488c865cfc1b9c47fb47 |
|---|
| Source note | uspto-grants-2013_12 |
|---|
