Ethyl Acetate → 6-fluoro-N-[4-(6-methylimidazo[1,2-a]pyridin-2-yl)phenyl]pyridine-3-carboxamide

HRID 339561

Reaktionsgleichung

Reaktionsgleichung von HRID 339561
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][N:3]=1.[CH3:11][C:12]1[CH:13]=[CH:14][C:15]2[N:16]([CH:18]=[C:19]([C:21]3[CH:27]=[CH:26][C:24]([NH2:25])=[CH:23][CH:22]=3)[N:20]=2)[CH:17]=1.C(N(C(C)C)CC)(C)C.CCOC(C)=O>S(Cl)(Cl)=O.C1COCC1>[F:1][C:2]1[N:3]=[CH:4][C:5]([C:6]([NH:25][C:24]2[CH:23]=[CH:22][C:21]([C:19]3[N:20]=[C:15]4[CH:14]=[CH:13][C:12]([CH3:11])=[CH:17][N:16]4[CH:18]=3)=[CH:27][CH:26]=2)=[O:8])=[CH:9][CH:10]=1

Komponenten

7

Edukt 4

HCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 2428196-Fluoronicotinic AcidHCID 8210844-(6-Methylimidazo[1,2-a]pyridin-2-yl)aniline

Produkt 1

HCID 451374436-fluoro-N-[4-(6-methylimidazo[1,2-a]pyridin-2-yl)phenyl]pyridine-3-carboxamideAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 24386Thionyl ChlorideLösungsmittel

Versuchsvorschrift

A stirred suspension of 6-fluoronicotinic acid (80 mg, 0.414 mmol) in thionyl chloride (2 ml) was heated under reflux for 4 h. The excess reagent was then removed under reduced pressure to give a crude solid. The amide was prepared as described in the Amide Coupling section using the crude solid and 4-(6-methylimidazo[1,2-a]pyridin-2-yl)aniline (92 mg, 0.414 mmol) in dry THF (13 ml) and diisopropylethylamine (106 μl, 0.608 mmol) to give the title compound (86 mg, 60%) as a colourless solid after work-up and flash chromatography (EtOAc).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureunder reflux for 4 h
  3. customThe excess reagent was then removed under reduced pressure
  4. customto give a crude solid
  5. customThe amide was prepared

Quellen und Nachweise

ORD-Eintrag
ord-7cf5e04a419b44d5808a5e46fc0fa56c
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08895313B2

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