Cesium carbonate → methyl 3-[2-(2,4-difluorophenoxy)-6-oxo-6H-pyrido[1,2-b]pyridazin-5-yl]-4-methoxybenzoate

HRID 1454957Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1454957
Cl[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[CH:9][C:10](=[O:24])[C:11]=2[C:12]2[CH:13]=[C:14]([CH:19]=[CH:20][C:21]=2[O:22][CH3:23])[C:15]([O:17][CH3:18])=[O:16])[N:7]=1.C([O-])([O-])=O.[Cs+].[Cs+].[F:31][C:32]1[CH:37]=[C:36]([F:38])[CH:35]=[CH:34][C:33]=1[OH:39]>CN1C(=O)CCC1>[F:31][C:32]1[CH:37]=[C:36]([F:38])[CH:35]=[CH:34][C:33]=1[O:39][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[CH:9][C:10](=[O:24])[C:11]=2[C:12]2[CH:13]=[C:14]([CH:19]=[CH:20][C:21]=2[O:22][CH3:23])[C:15]([O:17][CH3:18])=[O:16])[N:7]=1

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 1230512,4-DifluorophenolHCID 57531227methyl 3-(2-chloro-6-oxo-6H-pyrido[1,2-b]pyridazin-5-yl)-4-methoxybenzoate

Produkt 1

HCID 57531245methyl 3-[2-(2,4-difluorophenoxy)-6-oxo-6H-pyrido[1,2-b]pyridazin-5-yl]-4-methoxybenzoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of methyl 3-(2-chloro-6-oxo-6H-pyrido[1,2-b]pyridazin-5-yl)-4-methoxybenzoate (1.05 g, 3.05 mmol) and Cs2CO3 (2.97 g, 9.15 mmol) dissolved in NMP (20 mL) was added 2,4 difluoro phenol (475 mg, 3.66 mmol). The mixture was heated to 80° C. for 1 hr until the reaction was complete via LCMS analysis. The reaction was poured into 500 mL of ice/H2O and the solid precipitate was collected. The crude residue was purified via silica gel chromatography (EtOAc/CH2Cl2, MeOH) to yield the title compound.

Aufarbeitung

  1. customthe solid precipitate was collected
  2. customThe crude residue was purified via silica gel chromatography (EtOAc/CH2Cl2, MeOH)

Quellen und Nachweise

ORD-Eintrag
ord-0ce05da8e0d7418d92f6486c5635e4d1
Quelldatensatz
uspto-grants-2009_01
Patentnummer
US07482345B2

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