Ethyl Acetate → 1-[5-Chloro-8-(2-fluorophenyl)quinolin-7-yl]ethanamine
Reaction equation
[N:1]([CH:4]([C:6]1[C:15]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[F:22])=[C:14]2[C:9]([CH:10]=[CH:11][CH:12]=[N:13]2)=[C:8]([Cl:23])[CH:7]=1)[CH3:5])=[N+]=[N-].CP(C)C.C(OCC)(=O)C>O1CCCC1.O>[Cl:23][C:8]1[CH:7]=[C:6]([CH:4]([NH2:1])[CH3:5])[C:15]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[F:22])=[C:14]2[C:9]=1[CH:10]=[CH:11][CH:12]=[N:13]2Participants
Procedure
To a stirred solution of 7-(1-azidoethyl)-5-chloro-8-(2-fluorophenyl)quinoline (0.037 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 showed two peaks by LCMS with the same desired mass and was used directly in the next step (28 mg, 82%). LCMS calculated for C17H15ClFN2(M+H)+: m/z=301.1; found: 301.0.
Workup
- extractionthe mixture was extracted with 1 N HCl twice
- extractionextracted with dichloromethane
- washThe combined organic layers were washed with brine
- dry with materialdried over magnesium sulfate
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-4f026b5251ab443abf5a5c9c70983bcd
- Source dataset
- uspto-grants-2014_03
- Patent number
- US08680108B2
Reaction notes
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