Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | Trimethylphosphine | HCID 68983 | — |
| Reactant | HCID 86656168 | HCID 86656168 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 67249110 | HCID 67249110 | — |
Reaction Steps
To a stirred solution of 7-(1-azidoethyl)-8-(2-fluorophenyl)quinoline (0.033 g, 0.11 mmol) in tetrahydrofuran (0.3 mL) and water (0.0813 mL) was added 1.00 M trimethylphosphine in tetrahydrofuran (0.135 mL, 0.135 mmol) at room temperature and the mixture was stirred at room temperature for 1 hour. To the mixture was added ethyl acetate and the mixture was extracted with 1 N HCl twice. The combined extracts were neutralized with solid sodium bicarbonate, and extracted with dichloromethane. The combined organic layers were washed with brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue had two peaks with the same desired mass and was used directly in next step (25 mg, 83%). LCMS calculated for C17H16FN2(M+H)±: m/z=267.1; found: 267.1.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08680108B2 |
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| Source dataset | uspto-grants-2014_03 |
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| ORD ID | ord-57ccbf967241424e88c48de46c354951 |
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| Source note | uspto-grants-2014_03 |
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