Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Toluene | HCID 1140 | — |
| Reactant | Ammonium Chloride | HCID 25517 | — |
| Reactant | Potassium Phosphate, Tribasic | HCID 62657 | — |
| Reactant | 2-Cyclopropyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane | HCID 2758015 | — |
| Reactant | HCID 86673027 | HCID 86673027 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Product | HCID 86673036 | HCID 86673036 | 20% |
Reaction Steps
A solution of 6-bromo-2-isoquinolin-3-yl-chromen-4-one O-tert-butyl oxime (100 mg, 0.236 mmol), palladium acetate (3 mg, 0.014 mmol), potassium phosphate (175 mg, 0.826 mmol), dicyclohexylbiphenylphosphine (8 mg, 0.024 mmol), Cyclopropylboronic acid pinacol ester (99 mg, 0.59 mmol) in toluene (3 ml) was degassed with argon for 10 min. The reactor was sealed and heated at 120° C. for 18 hours. The mixture was poured onto a saturated aqueous solution of ammonium chloride, extracted with ethyl acetate, washed with water and brine, dried over sodium sulfate and purified by flash chromatography over silica gel (cyclohexane/dichloromethane: 0-80%) to yield 2-isoquinolin-3-yl-7-(pyridin-2-yl-ethynyl)-chromen-4-one O-tert-butyl oxime (18 mg, 20%).
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-a614c461a5c6435a99c6c660cddfda8a |
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| Source note | uspto-grants-2015_02 |
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