Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 5-Bromo-2,3-difluoropyridine | HCID 14549654 | — |
| Reactant | tert-butyl 4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole-1-carboxylate | HCID 16217654 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 86696253 | HCID 86696253 | 53.5% |
Reaction Steps
5-bromo-2,3-difluoropyridine (2.0 g, 10.31 mmol), tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole-1-carboxylate (3.03 g, 10.31 mmol), Na2CO3 (2.186 g, 20.62 mmol) and Pd(Ph3P)4 (1.191 g, 1.031 mmol) were dissolved in dioxane (20 ml). The mixture was bubbled with Ar for 10 min. The reaction was stirred at 100° C. for overnight, cooled and concentrated under reduced pressure. The residue was purified by silica gel chromatography (DCM/MeOH=30/1) to afford the title compound as white solid (1.0 g, 53.5% yield). LCMS (method B): [M+H]+=182, tR=1.98 min.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09062045B2 |
|---|
| Source dataset | uspto-grants-2015_06 |
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| ORD ID | ord-d7a8ee584d674ced85ece71ce3e3ec71 |
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| Source note | uspto-grants-2015_06 |
|---|