Optimization attempts for Buchwald–Hartwig cross-coupling reaction on compound 2.
| |||
|---|---|---|---|
| Entry | Base | Phosphine | Putative outcomea |
| 1 | tBuONa | XPhos | Cyclopropylamine introduced at position 5 – saponification of the methyl ester |
| 2 | Cs2CO3 | XPhos | Homocoupling of 2 |
| 3 | LiHMDS | XPhos | Conversion of the methyl ester into cyclopropylamide |
| 4 | Cs2CO3 | BrettPhos | Homocoupling of 2 |
from LCMS observations.