6-Bromo-5-fluoroquinoline → (5-Fluoro-quinolin-6-yl)-acetic acid tert-butyl ester

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Reaktionsgleichung

Br[C:2]1[C:3]([F:12])=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[CH:5]2.[C:13]([O-:16])(=[O:15])[CH3:14].[Br-].[C:18]([Zn+2])([CH3:21])([CH3:20])[CH3:19]>O1CCCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:18]([O:15][C:13](=[O:16])[CH2:14][C:2]1[C:3]([F:12])=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[CH:5]2)([CH3:21])([CH3:20])[CH3:19]

Komponenten

Reaktionsbedingungen

Temperatur: 120 °C

Versuchsvorschrift

To a solution of 6-bromo-5-fluoro-quinoline (1.0 g, 4.5 mmol) in tetrahydrofuran (1 mL) was added a solution of tert-butylzincbromide acetate (9 mmol, 20 mL, 10.4 M in tetrahydrofuran) followed by Pd(PPh3)4 (0.52 g, 0.45 mmol). The mixture was heated in a microwave reactor for 30 min at 120° C. The reaction mixture was quenched with a saturated ammonium chloride (60 mL), and extracted with ethyl acetate. The organic layer was dried over anhydrous Na2SO4, filtered and concentrated. The residue was purified by column chromatography to afford the title compound (0.83 g, 71%). 1H-NMR (CDCl3, 300 MHz): 8.9 (d, 1H), 8.4 (d, 1H), 7.8 (d, 1H), 7.6 (m, 1H), 7.5 (m, 1H), 3.7 (d, 2H), 1.4 (s, 9H).

Aufarbeitung

customThe reaction mixture was quenched with a saturated ammonium chloride (60 mL)
extractionextracted with ethyl acetate
dry with materialThe organic layer was dried over anhydrous Na2SO4
filtrationfiltered
concentrationconcentrated
customThe residue was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag: ord-3905cbd81c434a1f89d8eeb2344d4642
Quelldatensatz: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08071581B2

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