Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | 1,4-Dioxane | HCID 31275 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 1-methyl-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole | HCID 4912908 | — |
| Reactant | HCID 86681455 | HCID 86681455 | — |
| Catalyst | HCID 178418851 | HCID 178418851 | — |
| Product | HCID 86681454 | HCID 86681454 | 65.3% |
Reaction Steps
A mixture of 1-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (0.557 g, 2.68 mmol), bis(tri-t-butylphosphine)palladium (0.114 g, 0.223 mmol), 2-[(2S)-2-(5-bromo-1-oxo-1,3-dihydro-2H-isoindol-2-yl)-3-(3-fluorophenyl)propyl]-1H-isoindole-1,3(2H)-dione (1.10 g, 2.23 mmol) and N,N-diisopropylethylamine (1.16 mL, 6.69 mmol) in 1,4-dioxane (12 mL, 150 mmol) and water (0.60 mL, 33 mmol) was stirred under microwave at 110° C. for 15 minutes. The reaction mixture was filtered through a pad of celite and the filtrate was concentrated under reduced pressure. The residue was purified by combi-flash chromatography eluted with EtOAc/hexane (30-100%) to give 0.72 g (61% yield) of the desired product. LCMS found: 495.1 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08895571B2 |
|---|
| Source dataset | uspto-grants-2014_11 |
|---|
| ORD ID | ord-48338523239442e09562103fb9abc242 |
|---|
| Source note | uspto-grants-2014_11 |
|---|