Ethanol → Ethyl 5-fluoropyridine-2-carboxylate

HRID 130828

Reaktionsgleichung

Br[C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][N:3]=1.C[C:10]([O-:12])=[O:11].[Na+].ClCCl.[CH2:17](O)[CH3:18]>C1C=CC(P([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C1C=CC(P([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.[Fe]>[F:8][C:5]1[CH:6]=[CH:7][C:2]([C:10]([O:12][CH2:17][CH3:18])=[O:11])=[N:3][CH:4]=1

Komponenten

Reaktionsbedingungen

Temperatur: 90 °C

Versuchsvorschrift

To a Parr shaker add 2-bromo-5-fluoropyridine (Example 382, Part A) (7.00 g, 39.8 mmol), NaOAc (13.1 g, 159 mmol), absolute ethanol (100 mL) and [1,1-bis(diphenylphosphino)ferrocene]dichloropalladium(II):dichloromethane (1.62 g, 1.99 mmol). Charge the reaction vessel with 50 psi of CO. Heat at 90° C. for 18.25 hours. Cool the reaction mixture before filtering through a Celite® pad. Wash the pad with ethyl acetate, then concentrate the filtrate. Purify by flash chromatography, eluting with 25% ethyl acetate in hexanes to give the title compound (4.62 g, 68.6%): MS ES+ 169.9 (M+H)+, base peak MS ES+ 141.8 (M+H—CH2CH3)+; HPLC [YMC-Pack Pro C-18 (150×4.6 mm, S-5 microm), 0.1% TFA/acetonitrile in 0.1% TFA/water at 1.0 mL/min, 5-95% over 19 min], tR=10.3 min, 97.0 purity.

Aufarbeitung

additionCharge the reaction vessel with 50 psi of CO
temperatureCool the reaction mixture
filtrationbefore filtering through a Celite® pad
washWash the pad with ethyl acetate
concentrationconcentrate the filtrate
customPurify by flash chromatography
washeluting with 25% ethyl acetate in hexanes

Quellen und Nachweise

ORD-Eintrag: ord-9610ccb898bb4898a89489dce9229c83
Quelldatensatz: uspto-grants-2008_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07381719B2

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