Ethyl Acetate → tert-butyl 4-(5-cyclopropyl-3-iodo-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate

HRID 387529Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 387529
Cl[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][CH:4]=1.[CH:11]1([C:14]2[C:15]([N:24]3[CH2:29][CH2:28][N:27]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:26][CH2:25]3)=[C:16]3[C:22]([I:23])=[N:21][NH:20][C:17]3=[N:18][CH:19]=2)[CH2:13][CH2:12]1.C(=O)([O-])[O-].[K+].[K+].CCOC(C)=O>CN(C=O)C.O>[CH:11]1([C:14]2[C:15]([N:24]3[CH2:29][CH2:28][N:27]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:26][CH2:25]3)=[C:16]3[C:22]([I:23])=[N:21][N:20]([CH2:2][C:3]4[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][CH:4]=4)[C:17]3=[N:18][CH:19]=2)[CH2:12][CH2:13]1

Komponenten

7

Edukt 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 699934-Methyloxybenzyl chlorideHCID 178452207HCID 178452207, Verbindung

Produkt 1

HCID 68761344tert-butyl 4-(5-cyclopropyl-3-iodo-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylateAusbeute 57,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

1-(Chloromethyl)-4-methoxybenzene (0.734 g, 4.69 mmol) was slowly added to a stirring mixture of tert-butyl 4-(5-cyclopropyl-3-iodo-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate (2.00 g, 4.26 mmol) and potassium carbonate (0.883 g, 6.39 mmol) in DMF (30 mL) at room temperature, and the reaction was then stirred for 2 hours. EtOAc (200 mL) and water (100 mL) were added to the mixture, and the phases were separated. The organic suspension was washed with water (3×50 mL), dried (MgSO4), filtered, and concentrated in vacuo to provide the crude as an oil. The residue was purified by flash chromatography on silica gel (Biotage Flash 40M+) eluting with 15% EtOAc/hexane to provide tert-butyl 4-(5-cyclopropyl-3-iodo-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate (1.44 g, 57% yield) as a solid.

Aufarbeitung

  1. customthe phases were separated
  2. washThe organic suspension was washed with water (3×50 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto provide the crude as an oil
  7. customThe residue was purified by flash chromatography on silica gel (Biotage Flash 40M+)
  8. washeluting with 15% EtOAc/hexane

Quellen und Nachweise

ORD-Eintrag
ord-e6901438a55e4b84a7b66ec940023126
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08372842B2

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