Acetonitrile → 1-(3,3,4,4,4-pentafluorobutyl)-1H-pyrazolo[3,4-b]pyridine-3-carbonitrile

HRID 2203350Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2203350
C(#N)C.[NH:4]1[C:8]2=[N:9][CH:10]=[CH:11][CH:12]=[C:7]2[C:6]([C:13]#[N:14])=[N:5]1.C(=O)([O-])[O-].[K+].[K+].[F:21][C:22]([F:30])([F:29])[C:23]([F:28])([F:27])[CH2:24][CH2:25]I>CCOC(C)=O>[F:27][C:23]([F:28])([C:22]([F:30])([F:29])[F:21])[CH2:24][CH2:25][N:4]1[C:8]2=[N:9][CH:10]=[CH:11][CH:12]=[C:7]2[C:6]([C:13]#[N:14])=[N:5]1

Komponenten

6

Edukt 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 1100921,1,1,2,2-Pentafluoro-4-iodobutaneHCID 178510690HCID 178510690, Verbindung

Produkt 1

HCID 866789821-(3,3,4,4,4-pentafluorobutyl)-1H-pyrazolo[3,4-b]pyridine-3-carbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

An acetonitrile solution (150 mL) containing the intermediate from Step C above (10.5 g, 43.7 mmol), potassium carbonate (30.2 g, 219 mmol) and 1,1,1,2,2-pentafluoro-4-iodobutane (23.95 g, 87 mmol) was heated at 75° C. for 48 hours. The reaction solution was cooled to room temperature and diluted with EtOAc. The solution was washed with water, brine and concentrated in vacuo. The residue was purified by silica gel chromatography using a hexanes/EtOAc gradient to give the title compound. 1H NMR (400 MHz, CH3CN-d3): δ 8.71 (dd, J=4.47, 1.51 Hz, 1H); 8.31 (dd, J=8.22, 1.52 Hz, 1H); 7.44 (dd, J=8.24, 4.48 Hz, 1H); 4.92 (t, J=6.98 Hz, 3H); 3.00-2.82 (m, 2H). m/z=291.0 (M+H).

Aufarbeitung

  1. temperatureThe reaction solution was cooled to room temperature
  2. washThe solution was washed with water, brine
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-0b9bc2d444314247a59829f642c0b6e9
Quelldatensatz
uspto-grants-2016_06
Patentnummer
US09365574B2

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