Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Tetrahydrofuran | HCID 8028 | — |
| Reactant | HCID 58875334 | HCID 58875334 | — |
| Reactant | HCID 178418336 | HCID 178418336 | — |
| Solvent | Trifluoroacetic acid | HCID 6422 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Solvent | Acetonitrile--water (1/1) | HCID 18373917 | — |
| Product | HCID 58387934 | HCID 58387934 | 19% |
Reaction Steps
To a mixture of quinoline-6-carboxylic acid 3-bromobenzylamide described in Preparation Example E+-8 (8.0 mg, 0.023 mmol), dichloro(1,1′-bis(diphenylphosphino)ferrocene)nickel(II) (3.2 mg, 0.0047 mmol) and tetrahydrofuran (1 mL) was added benzylmagnesium chloride (1.1M tetrahydrofuran solution, 0.088 mL, 0.094 mmol) at room temperature, and the solution was stirred for 30 minutes at 50° C. After cooling, water and ethyl acetate were added for extraction, the solution was washed with brine, the solvent was then evaporated in vacuo. The residue was purified by reverse phase high performance liquid chromatography (acetonitrile-water mobile phase (containing 0.1% trifluoroacetic acid) was used), and trifluoroacetic acid salt of the title compound (2.1 mg, 0.0045 mmol, 19%) was obtained.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07932272B2 |
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| Source dataset | uspto-grants-2011_04 |
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| ORD ID | ord-4fd71c99aea54d3caf6267e27c17255b |
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| Source note | uspto-grants-2011_04 |
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