1-Propanol → 4-(2-aminophenyl)-1,5-dimethyl-1H-pyrazole-3-carbonitrile

HRID 1360402

Reaktionsgleichung

Br[C:2]1[C:3]([C:9]#[N:10])=[N:4][N:5]([CH3:8])[C:6]=1[CH3:7].[NH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+].C(O)CC>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>[NH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:2]1[C:3]([C:9]#[N:10])=[N:4][N:5]([CH3:8])[C:6]=1[CH3:7]

Komponenten

Reaktionsbedingungen

Temperatur: 100 °C

Versuchsvorschrift

Triphenylphosphine (2.4 mg, 0.09 mmol) and palladium (II) acetate (7 mg, 0.03 mmol) were added to a mixture of 4-bromo-1,5-dimethyl-1H-pyrazole-3-carbonitrile (0.600 g, 3.00 mmol), 2-aminophenylboronic acid (0.719 g, 5.25 mmol), aqueous sodium carbonate (1.8 mL of 2 M), propanol (5.25 mL) and water (1.1 mL). The reaction was heated under a nitrogen atmosphere at 100° C. for three hours and then allowed to cool to ambient temperature. The work-up procedure described in Part G of Examples 1-4 was followed. The resulting orange oil was purified by chromatography on a HORIZON HPFC system (25+M cartridge, eluting with ethyl acetate/hexane ranging in ratios from 50:50 to 75:25) to provide 371 mg of 4-(2-aminophenyl)-1,5-dimethyl-1H-pyrazole-3-carbonitrile as a pale yellow solid.

Aufarbeitung

temperatureto cool to ambient temperature
customThe resulting orange oil was purified by chromatography on a HORIZON HPFC system (25+M cartridge, eluting with ethyl acetate/hexane ranging in ratios from 50:50 to 75:25)

Quellen und Nachweise

ORD-Eintrag: ord-bc21828950544d12a4e54471bc0ab21b
Quelldatensatz: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07879849B2

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