HuagongsheHuagongshe Chemistry Print Report · For research reference only
Tetrahydrofuran → [4-(1-Cyclopropyl-4,4-dimethyl-1,2,3,4-tetrahydro-quinolin-6-yl-ethynyl)phenyl]acetic Acid Methyl Ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Tetrahydrofuran | HCID 8028 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Methyl 4-Iodophenylacetate | HCID 10378700 | — |
| Reactant | 4-[(8-Cyclopropyl-3 4-dihydro-4,4-dimethylspiro[2H-1-benzopyran-2,1'-cyclopropane]-6-yl)ethynyl]-2-fluoro-benzoic acid methyl ester | HCID 69548418 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Hexane | HCID 8058 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | [4-(1-Cyclopropyl-4,4-dimethyl-1,2,3,4-tetrahydro-quinolin-6-yl-ethynyl)phenyl]acetic Acid Methyl Ester | HCID 10270709 | — |
Reaction Steps
Following general procedure F and using 1-cyclopropyl-6-ethynyl-4,4-dimethyl-1,2,3,4-tetrahydro quinoline (Intermediate 53, 0.05 g, 0.22 mmol), methyl-4-iodo-phenyl acetate (Reagent B, 0.055 g, 0.2 mmol), triethyl amine (5 mL), tetrahydrofuran, copper(I)iodide (0.025 g, 0.13 mmol) and dichlorobis(triphenylphosphine)palladium(II) (0.75 g, 0.11 mmol) followed preparative normal phase HPLC using 10% ethyl acetate in hexane as the mobile phase, the title compound was obtained (0.089 g, 100%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06369225B1 |
| Source dataset | uspto-grants-2002_04 |
| ORD ID | ord-311e01b86f3042afb9fb2c46c0a42c4c |
| Source note | uspto-grants-2002_04 |