2,2'-Bipyridine → 1,5-Dicyclopropyl-3-(2,5-dimethyl-pyrrol-1-yl)-1H-pyrazole

HRID 45153

Reaktionsgleichung

N1C=CC=CC=1[C:7]1[CH:12]=[CH:11]C=CN=1.[CH:13]1([C:16]2[NH:20][N:19]=[C:18]([N:21]3[C:25]([CH3:26])=[CH:24][CH:23]=[C:22]3[CH3:27])[CH:17]=2)[CH2:15][CH2:14]1.C(=O)([O-])[O-].[Na+].[Na+]>ClCCCl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH:11]1([N:20]2[C:16]([CH:13]3[CH2:15][CH2:14]3)=[CH:17][C:18]([N:21]3[C:25]([CH3:26])=[CH:24][CH:23]=[C:22]3[CH3:27])=[N:19]2)[CH2:12][CH2:7]1

Komponenten

Reaktionsbedingungen

Temperatur: 70 °C

Versuchsvorschrift

A suspension of copper (II) acetate (0.902 g, 4.97 mmol) and 2,2′-bipyridine (0.776 g, 4.97 mmol) in DCE (20 mL) is stirred at 70° C. for 15 min, then transferred to a suspension of cyclopropyl trifluoroborate potassium salt (1.47 g, 9.94 mmol) and 5-Cyclopropyl-3-(2,5-dimethyl-pyrrol-1-yl)-1H-pyrazole (1 g, 4.97 mmol), and sodium carbonate (1.053 g, 9.94 mmol) in DCE (40 mL). The resulting dark-green mixture is stirred at 70° C. for 24 h. T The reaction mixture is partitioned between EtOAc and 1N HCl. The aqueous layer is extracted with EtOAc. The combined organic layers are washed with brine, dried (Na2SO4) and concentrated. The residue (1.64 g) is purified by ISCO (EtOAc-heptane 0-30%) to provide the desired product (1.25 g) as a colorless oil. MS (ESI) m/z 242.3 (M+1).

Aufarbeitung

stirringThe resulting dark-green mixture is stirred at 70° C. for 24 h
customT The reaction mixture is partitioned between EtOAc and 1N HCl
extractionThe aqueous layer is extracted with EtOAc
washThe combined organic layers are washed with brine
dry with materialdried (Na2SO4)
concentrationconcentrated
customThe residue (1.64 g) is purified by ISCO (EtOAc-heptane 0-30%)

Quellen und Nachweise

ORD-Eintrag: ord-d2d5fd8e56d141a08b39d578e86e99af
Quelldatensatz: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08541432B2

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