Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | 75053-81-5 | HCID 12940619 | — |
| Reactant | (1-((2-(Trimethylsilyl)ethoxy)methyl)-1H-pyrazol-5-yl)boronic acid | HCID 21874652 | — |
| Reactant | Water ethylacetate | HCID 22728543 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | 1,2-Dimethoxyethane | HCID 8071 | — |
| Solvent | Sodium Carbonate | HCID 10340 | — |
| Product | HCID 71227825 | HCID 71227825 | — |
Reaction Steps
A suspension of Intermediate E (6.0 g, 23 mmol) and 1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazole-5-boronic acid (SM-2) (6.6 g, 27 mmol) in a mixture of DME (60 mL) and 2N aqueous Na2CO3 (33 mL) is sparged with Argon for 30 minutes. The mixture is treated with tetrakis(triphenylphosphine)palladium(0) (2.6 g, 2 mmol) and heated to 100° C. for 16 hours. The solution is cooled, poured into water/EtOAc, and the organic layer is collected. The aqueous layer is extracted twice with EtOAc, and the combined organic layers are washed with brine, dried over Na2SO4, filtered and concentrated. The residue is purified on SiO2 (EtOAc/heptanes) to provide F.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09139567B2 |
|---|
| Source dataset | uspto-grants-2015_09 |
|---|
| ORD ID | ord-53916348739c4d508ea2171794da36ef |
|---|
| Source note | uspto-grants-2015_09 |
|---|
