[5-(4-fluoro-benzylamino)-2-(4-methoxy-benzyl)-2H-pyrazol-3-yl]-methanol → 5-(4-fluoro-benzylamino)-2-(4-methoxy-benzyl)-2H-pyrazole-3-carbaldehyde

HRID 509965Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 509965
[F:1][C:2]1[CH:25]=[CH:24][C:5]([CH2:6][NH:7][C:8]2[CH:9]=[C:10]([CH2:22][OH:23])[N:11]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=3)[N:12]=2)=[CH:4][CH:3]=1>[O-2].[Mn+4].[O-2].ClCCl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][NH:7][C:8]2[CH:9]=[C:10]([CH:22]=[O:23])[N:11]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=3)[N:12]=2)=[CH:24][CH:25]=1

Komponenten

4

Edukt 1

HCID 58259462[5-(4-fluoro-benzylamino)-2-(4-methoxy-benzyl)-2H-pyrazol-3-yl]-methanol

Produkt 1

HCID 582591365-(4-fluoro-benzylamino)-2-(4-methoxy-benzyl)-2H-pyrazole-3-carbaldehydeAusbeute 98,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418406HCID 178418406, VerbindungKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

In a round bottom flask, [5-(4-fluoro-benzylamino)-2-(4-methoxy-benzyl)-2H-pyrazol-3-yl]-methanol (112, 1.6 g, 4.2 mmol) was combined with 300 mL of dichloromethane and manganese(IV) oxide (0.61 g, 7.0 mmol) and stirred overnight under nitrogen. The reaction was filtered through celite and the filtrate concentrated under vacuum. The resulting material was purified by silica gel column chromatography, eluting with 10-100% ethyl acetate in hexane. Appropriate fractions were combined and concentrated under vacuum to provide the desired compound (113, 1.4 g). 1H NMR was consistent with the compound structure.

Aufarbeitung

  1. filtrationThe reaction was filtered through celite
  2. concentrationthe filtrate concentrated under vacuum
  3. customThe resulting material was purified by silica gel column chromatography
  4. washeluting with 10-100% ethyl acetate in hexane
  5. concentrationconcentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-82c4454fbf81408cbbd7e7bf7471b828
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09096593B2

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