Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Triphenylphosphine | HCID 11776 | — |
| Reactant | Ethynylpyridine | HCID 137268 | — |
| Reactant | Sodium | HCID 5360545 | — |
| Reactant | HCID 86673023 | HCID 86673023 | — |
| Catalyst | Copper iodide | HCID 83717 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 86673036 | HCID 86673036 | 64.1% |
Reaction Steps
A solution of 7-bromo-2-isoquinolin-3-yl-chromen-4-one O-tert-butyl oxime (150 mg, 0.35 mmol), trans-dichlorobis(triphenylphosphine)palladium (22 mg, 0.035 mmol), copper iodide (13 mg, 0.071 mmol), triphenylphosphine (19 mg, 0.071 mmol) in dimethylformamide (3 ml) was degassed with argon for 10 min and then treated with triethylamine (74 μl, 0.53 mmol) and 2-ethynylpyridine (45 μl, 0.45 mmol). The solution was warmed to 120° C. under microwave irradiation (power max=80 W) for 1 hour and then poured onto a saturated aqueous solution of sodium hydrogenocarbonate, extracted with ethyl acetate, washed with water and brine, dried over sodium sulfate and purified by flash chromatography over silica gel (cyclohexane/ethyl acetate: 20-40%) to yield 2-isoquinolin-3-yl-7-(pyridin-2-yl-ethynyl)-chromen-4-one O-tert-butyl oxime (100 mg, 63%) as a yellow solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08962627B2 |
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| Source dataset | uspto-grants-2015_02 |
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| ORD ID | ord-d073a75929794b2a952922be81893371 |
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| Source note | uspto-grants-2015_02 |
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