HuagongsheHuagongshe Chemistry Print Report · For research reference only
Potassium Carbonate → 3-[4-(4-Cyano-phenyl)-pyrazol-1-ylmethyl]-benzoic acid methyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 4-Cyanophenylboronic acid | HCID 2734326 | — |
| Reactant | methyl 3-[(4-bromo-1H-pyrazol-1-yl)methyl]benzoate | HCID 17024610 | — |
| Product | 3-[4-(4-Cyano-phenyl)-pyrazol-1-ylmethyl]-benzoic acid methyl ester | HCID 67508533 | 32% |
Reaction Steps
Charge a microwave vial with 3-(4-bromo-pyrazol-1-ylmethyl)-benzoic acid methyl ester (0.60 g, 2.00 mmol), 4-cyanophenylboronic acid (0.35 g, 2.40 mmol), potassium carbonate (0.50 g, 4.80 mmol) and tetrakistriphenylphosphine palladium (0) (0.23 g, 0.2 mmol). Flush the vessel with inert gas and seal. Dissolve the contents of the vial in 10 mL of a 4:1 dioxane-water mixture and microwave at 150° C. for 5 minutes. Dilute the reaction mixture with EtOAc, dry over sodium sulfate, filter and concentrate to give an oil. Purify the residue by flash chromatography using a gradient of 0-50% EtOAc/hexanes to afford 0.20 g, 32% yield of 3-[4-(4-cyano-phenyl)-pyrazol-1-ylmethyl]-benzoic acid methyl ester as a solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09000154B2 |
| Source dataset | uspto-grants-2015_04 |
| ORD ID | ord-47a00b2feb4845f982e521bbacb817ad |
| Source note | uspto-grants-2015_04 |