Triphenylphosphine → HCID 57707801, compound
Reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cl:20][C:21]1[C:30]([C@H:31](O)[CH3:32])=[CH:29][C:28]2[C:23](=[C:24]([F:34])[CH:25]=[CH:26][CH:27]=2)[N:22]=1.C1(P([N:49]=[N+:50]=[N-:51])(C2C=CC=CC=2)=O)C=CC=CC=1>C1COCC1>[N:49]([C@H:31]([C:30]1[C:21]([Cl:20])=[N:22][C:23]2[C:28]([CH:29]=1)=[CH:27][CH:26]=[CH:25][C:24]=2[F:34])[CH3:32])=[N+:50]=[N-:51]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
Triphenylphosphine (1.81 g, 6.9 mmol, 1.2 eq) was dissolved in anhydrous THF (30 mL) and cooled to 0° C. To this solution was added diispropylazodicarboxylate (1.36 mL, 6.9 mmol, 1.2 eq). The reaction was stirred for 30 minutes at 0° C. and (R)-1-(2-chloro-8-fluoroquinolin-3-yl)ethanol (1.3 g, 5.7 mmol) in 30 mL of THF was added, followed by diphenylphosphoryl azide (1.37 mL, 6.3 mmol, 1.1 eq). The reaction was allowed to warm to rt and stir at rt overnight. The reaction was deposited on silica gel and concentrated. Purification by column chromatography (3% etoac in hexanes) afforded (S)-3-(1-azidoethyl)-2-chloro-8-fluoroquinoline. 1H NMR (400 MHz, CDCl3) δ ppm 8.30 (d, J=1.2 Hz, 1H), 7.67 (br d, J=8.22 Hz, 1H), 7.54 (td, J=7.8, 4.7 Hz, 1H), 7.45 (ddd, J=10.2, 7.8, 1.2 Hz) δ 5.22 (q, J=6.7 Hz, 1H), 1.68 (d, J=6.7 Hz, 3H). Mass Spectrum (ESI) m/e=250.9 (M+1). General Procedures for 8-fluoroquinoline Analogues:
Workup
- additionTo this solution was added diispropylazodicarboxylate (1.36 mL, 6.9 mmol, 1.2 eq)
- temperatureto warm to rt
- stirringstir at rt overnight
- concentrationconcentrated
- customPurification by column chromatography (3% etoac in hexanes)
Sources & evidence
- ORD record
- ord-8e0b247795804a43ae07d12fd09ca9eb
- Source dataset
- uspto-grants-2012_06
- Patent number
- US08193199B2
Reaction notes
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