HuagongsheHuagongshe Chemistry Print Report · For research reference only
Potassium Carbonate → tert-Butyl 7-(4-(trifluoromethyl)phenyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 4-(Trifluoromethyl)phenylboronic acid | HCID 2734389 | — |
| Reactant | tert-Butyl 7-bromo-3,4-dihydroisoquinoline-2(1H)-carboxylate | HCID 15885175 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Ethanol toluene water | HCID 86587398 | — |
| Product | tert-Butyl 7-(4-(trifluoromethyl)phenyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate | HCID 70974981 | 92.7% |
Reaction Steps
A mixture 4-(trifluoromethyl)phenylboronic acid (987 mgs, 5.2 mmol), 7-Bromo-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester (1.2 g, 4.0 mmol), potassium carbonate (1.1 g, 8.0 mmol), PdCl2(dppf) (146 mgs, 0.2 mmol) in toluene/ethanol/water (3 mL/1.5 mL/1.5 mL) was heated in pressure vessel at 120° C. for 2 h. The mixture was then concentrated and chromatographed (40 grams of SiO2, 30% EtOAc/hexanes) to provide the title compound (1.4 g, 92% yield over two steps).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09403782B2 |
| Source dataset | uspto-grants-2016_08 |
| ORD ID | ord-2ac6344b8e1548319751ec0f185ba9e4 |
| Source note | uspto-grants-2016_08 |