Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Toluene | HCID 1140 | — |
| Reactant | Potassium Phosphate, Tribasic | HCID 62657 | — |
| Reactant | Ethylboronic acid | HCID 521157 | — |
| Reactant | HCID 67773046 | HCID 67773046 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 67775631 | HCID 67775631 | 54.3% |
Reaction Steps
Under argon gas atmosphere, a mixture of methyl 4-bromo-1-(2,4,6-trifluorophenyl)isoquinoline-7-carboxylate (150 mg), ethylboronic acid (84 mg), tetrakis(triphenylphosphine)palladium (44 mg), tripotassium phosphate (241 mg), toluene (5 mL), and water (0.3 mL) was heated under stirring in an oil bath at 100° C. for one day. The reaction mixture was returned to room temperature, and diluted with water and ethyl acetate, and then the insoluble matter was separated by filtration. The filtrate was extracted with ethyl acetate, and the organic layer was concentrated under reduced pressure. The resulting residue was purified under silica gel column chromatography (hexane/ethyl acetate) to obtain methyl 4-ethyl-1-(2,4,6-trifluorophenyl)isoquinoline-7-carboxylate (71 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08853242B2 |
|---|
| Source dataset | uspto-grants-2014_10 |
|---|
| ORD ID | ord-e4f708e2e10d48a5ae7c66edb48efee1 |
|---|
| Source note | uspto-grants-2014_10 |
|---|