Ammonium Chloride → 6-(4-Benzyloxy-2-fluoro-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carbaldehyde

HRID 2279168Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2279168
CON(C)[C:4]([C:6]1[C:7]2[C:29]([CH3:30])=[N:28][N:27]([CH:31]3[CH2:36][CH2:35][CH2:34][CH2:33][O:32]3)[C:8]=2[N:9]=[C:10]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[CH:14][C:13]=2[F:26])[CH:11]=1)=[O:5].C[Mg]Br.[Cl-].[NH4+]>C1COCC1>[CH2:19]([O:18][C:15]1[CH:16]=[CH:17][C:12]([C:10]2[N:9]=[C:8]3[N:27]([CH:31]4[CH2:36][CH2:35][CH2:34][CH2:33][O:32]4)[N:28]=[C:29]([CH3:30])[C:7]3=[C:6]([CH:4]=[O:5])[CH:11]=2)=[C:13]([F:26])[CH:14]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Komponenten

5

Edukt 3

HCID 25517Ammonium ChlorideHCID 900139076-(4-benzyloxy-2-fluoro-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid methoxy-methyl-amideHCID 178418573HCID 178418573, Verbindung

Produkt 1

HCID 900301886-(4-Benzyloxy-2-fluoro-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carbaldehydeAusbeute 113,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

6-(4-Benzyloxy-2-fluoro-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid methoxy-methyl-amide (1.0 g) was dissolved in THF (25 mL). At 0° C. methylmagnesium bromide solution (1 M, 3.9 mL) was added slowly, the mixture was warmed to r.t. while stirring overnight. Saturated ammonium chloride solution was added, the mixture was extracted with dichloromethane, the organic phases were dried over magnesium sulfate and concentrated in a membrane pump vacuum. The residue was purified by fish chromatography (silica, heptane/ethyl acetate gradient) giving 1-[6-(4-benzyloxy-2-fluoro-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridin-4-yl]-methanone (1.0 g, quantitative yield with impurities).

Aufarbeitung

  1. extractionthe mixture was extracted with dichloromethane
  2. dry with materialthe organic phases were dried over magnesium sulfate
  3. concentrationconcentrated in a membrane pump vacuum
  4. customThe residue was purified by fish chromatography (silica, heptane/ethyl acetate gradient)

Quellen und Nachweise

ORD-Eintrag
ord-2b699af02f5e405192059cc52b65d73b
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09133181B2

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