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

HRID 1398450Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1398450
[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

To a solution of 4-chloro-5-fluoronicotinic acid (1.7 g, 9.68 mmol) in acetonitrile (18 mL) cooled to 0° C. was added DBU (3.65 mL, 24.21 mmol) dropwise. The reaction mixture was stirred for 30 min. To this mixture iodomethane (3.03 mL, 48.4 mmol) was added dropwise and stirred at rt for 12 h. The volatiles were removed under reduced pressure. The residue was purified via silica gel column chromatography (hexane and ethyl acetate) to afford methyl 4-chloro-5-fluoronicotinate (1.2 g, 6.33 mmol, 65% yield) as a yellow solid. LC/MS (ESI) m/e 190.0 [(M+H)+, calcd for C7H6ClFNO2 189.9]; LC/MS retention time (method D): tR=0.77 min.

Aufarbeitung

  1. stirringstirred at rt for 12 h
  2. customThe volatiles were removed under reduced pressure
  3. customThe residue was purified via silica gel column chromatography (hexane and ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-4e9a630db9a94cae8443f414ddd2c21f
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08901305B2

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