Triphenylphosphine → HCID 57717615, Verbindung

HRID 1984402Notizen

Reaktionsgleichung

C(OC([NH:8]C1C=CN=CC=1B(O)O)=O)(C)(C)C.[CH2:18]([N:22]1[C:34]([CH2:35][CH:36]([CH3:38])[CH3:37])=[C:33]2[C:24]([C:25]([NH2:39])=[N:26][C:27]3[CH:28]=[CH:29]C=[CH:31][C:32]=32)=[N:23]1)[CH2:19][CH2:20][CH3:21].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:18]([N:22]1[C:34]([CH2:35][CH:36]([CH3:38])[CH3:37])=[C:33]2[C:24]([C:25]([NH2:39])=[N:26][C:27]3[CH:28]=[CH:29][N:8]=[CH:31][C:32]=32)=[N:23]1)[CH2:19][CH2:20][CH3:21]

Komponenten

Reaktionsbedingungen

Temperatur: 100 °C

Versuchsvorschrift

2-Butyl-1-(2-methylpropyl)-2H-pyrazolo[3,4-c]-1,6-naphthyridin-4-amine was synthesized from 4-[(tert-butoxycarbonyl)amino]pyridin-3-ylboronic acid (2.48 g, 10.4 mmol) and 4-bromo-1-butyl-5-(2-methylpropyl)-1H-pyrazole-3-carbonitrile (prepared as described in Parts A-F of Example 4, 1.56 g, 5.49 mmol) according to the reaction conditions described in Examples 52-54. Additional palladium (II) acetate (50 mg) and triphenylphosphine (170 mg) were added after the reaction had been heated for 23 hours. After the addition, the flask was placed under vacuum and back-filled with nitrogen twice. The solution was heated at 100° C. for an additional 29 hours. The reaction was worked-up and purified as described in Example 54, but was not recrystallized from acetonitrile, to provide 25 mg of 2-butyl-1-(2-methylpropyl)-2H-pyrazolo[3,4-c]-1,6-naphthyridin-4-amine as an off-white solid.

Aufarbeitung

customaccording to the reaction conditions
temperaturehad been heated for 23 hours
additionAfter the addition
additionback-filled with nitrogen twice
custompurified
customwas not recrystallized from acetonitrile

Quellen und Nachweise

ORD-Eintrag: ord-8dd92363c1964436a9dc87ac20cb0d0b
Quelldatensatz: uspto-grants-2009_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07544697B2

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