Sodium hydride → 5-Chloro-4-(oxetan-3-yloxy)-pyridine-2-carboxylic acid

HRID 1480068

Reaktionsgleichung

[Cl:1][C:2]1[C:3](I)=[CH:4][C:5]([C:8]([OH:10])=[O:9])=[N:6][CH:7]=1.[O:12]1[CH2:15][CH:14]([OH:16])[CH2:13]1.[H-].[Na+]>CN(C=O)C>[Cl:1][C:2]1[C:3]([O:16][CH:14]2[CH2:15][O:12][CH2:13]2)=[CH:4][C:5]([C:8]([OH:10])=[O:9])=[N:6][CH:7]=1

Komponenten

Reaktionsbedingungen

Temperatur: 120 °C

Versuchsvorschrift

To a solution of 5-chloro-4-iodo-pyridine-2-carboxylic acid (CAN 120643-06-3, 360 mg, 1.27 mmol) in DMF (10 mL) was added with stirring Oxetan-3-ol (CAN 7748-36-9, 104 mg, 1.4 mmol) and sodium hydride 60% (107 mg, 2.67 mmol). The resulting mixture was stirred at room temperature for 30 min and at 120° C. for 25 h, cooled and the reaction mixture was concentrated in vacuo. The residue was suspended with ethylacetate, transferred into a separatory funnel and extracted with 4.0 mL of 0.5M aqueous solution hydrochloric acid. The organic phase was collected and the aqueous phase was back-extracted with ethylacetate. The organic phases were combined, dried over sodium sulfate and evaporated down to dryness to give the title compound (323 mg, 111%) as a solid which was used crude without any further purification. MS (ESI, m/z): 228.4 (M−H+)

Aufarbeitung

temperaturecooled
concentrationthe reaction mixture was concentrated in vacuo
customtransferred into a separatory funnel
extractionextracted with 4.0 mL of 0.5M aqueous solution hydrochloric acid
customThe organic phase was collected
extractionthe aqueous phase was back-extracted with ethylacetate
dry with materialdried over sodium sulfate
customevaporated down to dryness

Quellen und Nachweise

ORD-Eintrag: ord-27090df4d3f247e4bf699d6a9f63829e
Quelldatensatz: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09409866B2

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