2-Amino-5-fluoro-N-methoxy-N-methylbenzamide → 3-Methylpyridine-2-carboxaldehyde

HRID 1616071

Reaktionsgleichung

Reaktionsgleichung von HRID 1616071
NC1C=CC(F)=CC=1[C:4](N(OC)C)=[O:5].C([Mg]Cl)(C)C.[CH3:20][C:21]1[C:22]([Mg]Br)=[N:23][CH:24]=[CH:25][CH:26]=1>C1COCC1>[CH3:20][C:21]1[C:22]([CH:4]=[O:5])=[N:23][CH:24]=[CH:25][CH:26]=1

Komponenten

5

Edukt 3

HCID 534075722-Amino-5-fluoro-N-methoxy-N-methylbenzamideHCID 178418918HCID 178418918, VerbindungHCID 178426302HCID 178426302, Verbindung

Produkt 1

HCID 15018743-Methylpyridine-2-carboxaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 2-amino-5-fluoro-N-methoxy-N-methylbenzamide (1.0 g, 5.05 mmol) in THF (4.2 mL) was added isopropylmagnesium chloride (2.0M in THF, 5.0 mL, 10.1 mmol) at −40° C. The temperature was allowed to rise to −10° C. over 40 min then was lowered to −40° C. in an acetonitrile/dry ice bath. 3-Methyl-2-pyridinylmagnesium bromide (0.25M in THF, 20.2 mL, 5.0 mmol) was added dropwise and the solution was allowed to rise to rt over one hour. The solution was partitioned between satd ammonium chloride solution and DCM; organic extracts were concentrated then purified by silica gel column chromatography eluting with a gradient of 10-70% EtOAc in hexane to afford 2-amino-5-fluorophenyl)(3-methylpyridin-2-yl)methanone as a yellow oil: LC-MS (ESI) m/z 231.2 [M+H]+.

Aufarbeitung

  1. customthen was lowered to −40° C. in an acetonitrile/dry ice bath
  2. waitto rise to rt over one hour
  3. customThe solution was partitioned between satd ammonium chloride solution and DCM
  4. concentrationorganic extracts were concentrated
  5. customthen purified by silica gel column chromatography
  6. washeluting with a gradient of 10-70% EtOAc in hexane

Quellen und Nachweise

ORD-Eintrag
ord-093185e68e544071a1aec297b85ac95c
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08765768B2

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