Sodium hydride → 4-((5-Fluoropyridin-2-yl)methoxy)pyridine 1-oxide

HRID 469680

Reaktionsgleichung

[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([OH:15])C2C=CC=CC=2)=[N:6][CH:7]=1.[H-].[Na+].Cl[C:19]1[CH:24]=[CH:23][N+:22]([O-:25])=[CH:21][CH:20]=1>CN(C=O)C.C(Cl)Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][O:15][C:19]2[CH:24]=[CH:23][N+:22]([O-:25])=[CH:21][CH:20]=2)=[N:6][CH:7]=1

Komponenten

Reaktionsbedingungen

Temperatur: 120 °C

Versuchsvorschrift

5-Fluoro-2-pyridylbenzylalcohol (3.00 g, 23.6 mmol) was dissolved in DMF (20 mL), and NaH (60% weight dispersion in mineral oil, 0.92 g, 23 mmol) was added. After stirring for 30 minutes, 4-chloropyridine-N-oxide (2.03 g, 15.7 mmol) was added, and the reaction mixture was heated for 1 h at 120° C. Upon cooling, the mixture was diluted with methylene chloride and washed with 5% lithium chloride solution (5×), dried and concentrated. Purification by flash column chromatography (40 g ISCO column eluting with methylene chloride and a methanol/ammonia mixture (10:1); gradient 100% methylene chloride to 90% methylene chloride over 30 min at 40 mL/min) provided the title compound (1.76 g, 50%) as a tan solid: 1H NMR (300 MHz, CDCl3) δ 8.48 (s, 1H), 8.12 (d, J=7.7 Hz, 2H), 7.48-7.46 (m, 2H), 6.90 (d, J=7.7 Hz, 2H), 5.20 (s, 2H).

Aufarbeitung

temperatureUpon cooling
washwashed with 5% lithium chloride solution (5×)
customdried
concentrationconcentrated
customPurification by flash column chromatography (40 g ISCO column
washeluting with methylene chloride

Quellen und Nachweise

ORD-Eintrag: ord-75aa3bbf67c1471e97b6bb59c095b18b
Quelldatensatz: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08629158B2

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