Trityl chloride → 4-iodo-1-trityl-1H-pyrazolo[3,4-b]pyridine

HRID 44667Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 44667
[I:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[NH:8][N:9]=[CH:10][C:3]=12.[H-].[Na+].[C:13](Cl)([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CN(C=O)C>[I:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8]([C:13]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)([C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)[C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[N:9]=[CH:10][C:3]=12

Komponenten

5

Edukt 3

HCID 6456Trityl chlorideHCID 24758Sodium hydrideHCID 576428014-Iodo-1H-pyrazolo[3,4-b]pyridine

Produkt 1

HCID 579696964-iodo-1-trityl-1H-pyrazolo[3,4-b]pyridineAusbeute 46 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Reaktionsbedingungen

Temperatur
5 °C

Versuchsvorschrift

4-iodo-1H-pyrazolo[3,4-b]pyridine (15 g, 61.22 mmol) was dissolved in DMF (300 mL) and the solution was cooled down in an ice bath to 5° C. Sodium hydride (60%, 2.938 g, 73.46 mmol) was added portionwise and left to stir at this temperature for 2 hours. After this time a solution of trityl chloride (18.77 g, 67.34 mmol) in DMF (150 mL) was added dropwise over 30 minutes. After an additional 2 hours of stirring, the solvent was removed by evaporation, and the residue was partitioned between ethyl acetate and saturated bicarbonate (2×100 ml). The organic layer was further washed with brine (100 ml), dried (MgSO4) and concentrated in vacuo to give a brown oil. This residue was purified on silica gel by flash column chromatography to afford the title compound as a white solid (13.71 g, 46% Yield). 1H NMR (DMSO-d6, 400 MHz) δ 7.16-7.31 (15H, m), 7.59 (1H, d), 7.89 (1H, d), 8.10 (1H, s); MS (ES+) 488.

Aufarbeitung

  1. waitleft
  2. stirringAfter an additional 2 hours of stirring
  3. customthe solvent was removed by evaporation
  4. customthe residue was partitioned between ethyl acetate and saturated bicarbonate (2×100 ml)
  5. washThe organic layer was further washed with brine (100 ml)
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. customto give a brown oil
  9. customThis residue was purified on silica gel by flash column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-abfeca800fac485b9dcc1304fb16aac5
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08541445B2

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