Methyl iodide → Methyl 4-chloro-5-fluoropyridine-3-carboxylate

HRID 2369520Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2369520
[Cl:1][C:2]1[C:7]([C:8]([OH:10])=[O:9])=[CH:6][N:5]=[CH:4][C:3]=1[F:11].[CH2:12]1CCN2C(=NCCC2)CC1.IC>C(#N)C>[Cl:1][C:2]1[C:7]([C:8]([O:10][CH3:12])=[O:9])=[CH:6][N:5]=[CH:4][C:3]=1[F:11]

Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 114579884-chloro-5-fluoropyridine-3-carboxylic acid

Produkt 1

HCID 86695923Methyl 4-chloro-5-fluoropyridine-3-carboxylateAusbeute 65,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A solution of 4-chloro-5-fluoronicotinic acid (1.7 g, 9.68 mmol) in acetonitrile (18 mL) was cooled to 0° C. To this solution was added DBU (3.65 mL, 24.21 mmol) dropwise and the resultant solution stirred for 30 min. Iodomethane (3.03 mL, 48.4 mmol) was added dropwise and stirred at room temperature for 12 h. The volatiles were removed completely under reduced pressure and the residue purified via silica gel chromatography using a gradient of ethyl acetate in hexane to afford methyl 4-chloro-5-fluoronicotinate (1.2 g, 6.33 mmol, 65% yield) as a yellow solid. LCMS (ESI) m/e 190.0 [(M+H)+, calcd for C7H6ClFNO2 190.0]; LC/MS retention time (Method F): tR=0.77 min.

Aufarbeitung

  1. customThe volatiles were removed completely under reduced pressure
  2. customthe residue purified via silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-b77ee4e194224869a196bf85a92c1e77
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08703953B2

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