Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Phenylacetylene | HCID 10821 | — |
| Reactant | (S)-2-tert-butoxy-2-(5-(4-chlorophenyl)-7-methyl-2-(trifluoromethylsulfonyloxy)quinolin-6-yl)ethyl pivalate | HCID 86691982 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178419050 | HCID 178419050 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 66630681 | HCID 66630681 | — |
Reaction Steps
The solution of (S)-2-tert-butoxy-2-(5-(4-chlorophenyl)-7-methyl-2-(trifluoromethylsulfonyloxy)quinolin-6-yl)ethyl pivalate (compound of Example 26) (35 mg, 0.06 mmol), ethynylbenzene (8 μL, 0.08 mmol), and triethylamine (1 mL) in ethyl acetate (0.5 mL) was degassed with nitrogen. Copper(I) iodide (1 mg) and bis(triphenylphosphine)palladium (II) dichloride (7 mg) were added, and the mixture was stirred for 12 hours. The mixture was diluted with ethyl acetate, washed with water and brine, and dried with sodium sulfate. Concentration and purification by flash column chromatography (silica gel, ethyl acetate/hexanes) gave (S)-2-tert-butoxy-2-(5-(4-chlorophenyl)-7-methyl-2-(phenylethynyl)quinolin-6-yl)ethyl pivalate. LCMS-ESI+ (m/z): [M+H]+ calcd for C35H37ClNO3: 554.2. Found: 554.3.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09296758B2 |
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| Source dataset | uspto-grants-2016_03 |
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| ORD ID | ord-b77194e33b754faab73e4c7966882b5d |
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| Source note | uspto-grants-2016_03 |
|---|
