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

HRID 2279113Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2279113
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[N:20]=[C:19]3[N:21]([CH:25]4[CH2:30][CH2:29][CH2:28][CH2:27][O:26]4)[N:22]=[C:23]([CH3:24])[C:18]3=[C:17]([CH2:31][OH:32])[CH:16]=2)=[C:11]([F:33])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>ClCCl>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:16]=[C:17]([CH:31]=[O:32])[C:18]3[C:23]([CH3:24])=[N:22][N:21]([CH:25]4[CH2:30][CH2:29][CH2:28][CH2:27][O:26]4)[C:19]=3[N:20]=2)=[C:11]([F:33])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

3

Edukt 1

HCID 118059348[6-(4-Benzyloxy-2-fluoro-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridin-4-yl]-methanol

Produkt 1

HCID 900301886-(4-Benzyloxy-2-fluoro-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carbaldehydeAusbeute 100,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

1.10 g of [6-(4-benzyloxy-2-fluoro-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridin-4-yl]-methanol were dissolved in 5 ml of dichloromethane. At 0° C. 0.52 g Dess-Martin-Periodinane were added. After 16 h at r.t. the reaction was diluted with dichloromethane, and washed subsequently with 1 N aqueous hydrochloric acid and sat. aqueous sodium hydrogencarbonate solution. The organic layer was then dried over sodium sulphate, filtered and concentrated in vacuo to yield 1.10 g (100%) of the crude title compound, which was used without further purification in the next step.

Aufarbeitung

  1. customAt 0° C
  2. washwashed subsequently with 1 N aqueous hydrochloric acid and sat. aqueous sodium hydrogencarbonate solution
  3. dry with materialThe organic layer was then dried over sodium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-0578672880aa4d1f8b76e79dba88645a
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09133181B2

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