Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | 1,4-Dioxane | HCID 31275 | — |
| Reactant | 1,8-Diazabicyclo(5.4.0)undec-7-ene | HCID 81184 | — |
| Reactant | Tricyclo(3.3.1.13,7)dec-1-ylmethylamine | HCID 86625 | — |
| Reactant | HCID 67203856 | HCID 67203856 | — |
| Catalyst | Molybdenum carbonyl (Mo(CO)6) | HCID 98885 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Product | HCID 24804720 | HCID 24804720 | — |
Reaction Steps
A 5-mL process vial was charged with (S)-2-(5-iodo-1-oxoisoquinolin-2(1H)-yl)propanamide (90 mg, 0.0003 mol), 1-adamantanemethylamine (90 mg, 0.0005 mol), molybdenum hexacarbonyl (90 mg, 0.0004 mol), palladium acetate (8 mg, 0.00004 mol), 1,8-diazabicyclo[5.4.0]undec-7-ene (80 mg, 0.0005 mol); and 1,4-dioxane (2 mL, 0.02 mol). The vessel was sealed under air and exposed to microwave heating for 15 min at 110° C. The reaction tube was thereafter cooled to room temperature, and the mixture was concentrated and dissolved in a small volume of dichloromethane. The crude product was purified via flash column chromatography (12 g of silica gel, 50-100% EtOAC/Hexane) then Prep. HPLC to give the desired product as a white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08779144B2 |
|---|
| Source dataset | uspto-grants-2014_07 |
|---|
| ORD ID | ord-67568e418d10414d8163f3b3013323e0 |
|---|
| Source note | uspto-grants-2014_07 |
|---|
