Reaktionsgleichung
C1(C2C=CC=CC=2)C=CC=CC=1C(P(C)C)P(C)C.[CH3:20][C:21]([CH3:24])([O-])C.[Na+].N#N.F[C:29]1[CH:30]=[C:31](CNC(=O)C)[C:32]([NH:45][C@H:46]([C:48]2[CH:53]=[CH:52][C:51]([F:54])=[CH:50][CH:49]=2)C)=[N:33][C:34]=1[NH:35][C:36]1[CH:40]=[C:39](OC(C)C)[NH:38][N:37]=1.C1(C2NN=C(N)C=2)CC1>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH:24]1([C:39]2[NH:38][N:37]=[C:36]([NH:35][C:34]3[CH:29]=[CH:30][CH:31]=[C:32]([NH:45][CH2:46][C:48]4[CH:49]=[CH:50][C:51]([F:54])=[CH:52][CH:53]=4)[N:33]=3)[CH:40]=2)[CH2:21][CH2:20]1Komponenten
Edukt 5
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Reaktionsbedingungen
- Temperatur
- 110 °C
Versuchsvorschrift
To a flask was added Pd(OAc)2 (22.4 mg, 0.1 mmol), (biphenyl-2-ylmethylene)bis(dimethylphosphine) (60 mg, 0.2 mmol) and sodium tert-butoxide (240 mg, 2.5 mmol). The flask was sealed and refilled with N2. To the mixture was added a solution of 6-bromo-N-(4-fluorobenzyl)pyridin-2-amine (Method 19; 281 mg, 1.0 mmol) and 5-cyclopropyl-1H-pyrazol-3-amine (123 mg, 1.0 mmol) in toluene (5 ml). The reaction mixture was heated at 110° C. overnight. The solvent was removed and EtOAc was added and the mixture was washed with brine and was concentrated. Semi-prep HPLC (Gilson) purification gave the title compound (6.4 mg, 2%). 1H NMR (CDCl3) δ 0.65 (m, 2H), 0.95 (m, 2H), 1.80 (m, 1H), 4.43 (m, 2H), 4.91 (br s, 1H), 5.60 (br s, 1H), 5.80 (m, 1H), 6.18 (m, 1H), 6.73 (m, 1H), 7.00 (m, 2H), 7.25 (m, 3H).
Aufarbeitung
- customThe flask was sealed
- customThe solvent was removed
- additionEtOAc was added
- washthe mixture was washed with brine
- concentrationwas concentrated
- customSemi-prep HPLC (Gilson) purification
Quellen und Nachweise
- ORD-Eintrag
- ord-3a4235c98ee84456bd161fecb0374e5c
- Quelldatensatz
- uspto-grants-2012_12
- Patentnummer
- US08324252B2
Verknüpfte Notizen
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