Potassium Carbonate → 2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]acetamide

HRID 1752567

Reaktionsgleichung

[CH3:1][C:2]1([CH3:14])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:10]=[N:11][NH:12][CH:13]=2)[O:3]1.Br[CH2:16][C:17]([NH2:19])=[O:18].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:1][C:2]1([CH3:14])[C:6]([CH3:7])([CH3:8])[O:5][B:4]([C:9]2[CH:13]=[N:12][N:11]([CH2:16][C:17]([NH2:19])=[O:18])[CH:10]=2)[O:3]1

Komponenten

Reaktionsbedingungen

Temperatur: 50 °C

Versuchsvorschrift

A suspension of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (2.00 g, 10.3 mmol), 2-bromoacetamide (2.14 g, 15.5 mmol), and potassium carbonate (2.14 g, 15.5 mmol) in acetone (60 mL) was heated at about 50° C. for about 3.5 days. The reaction mixture was then cooled to ambient temperature, filtered through diatomaceous earth, while washing with additional acetone, and then concentrated under reduced pressure. The crude material was then dissolved in a minimal amount of dichloromethane and purified via silica gel chromatography eluting with a gradient of 80-100% ethyl acetate in heptane to afford the title compound. 1H NMR (400 MHz, DMSO-d6) δ ppm 7.88 (s, 1H), 7.57 (s, 1H), 7.46 (s, 1H), 7.24 (s, 1H), 4.77 (s, 2H), 1.26 (s, 12H). MS (ESI+) m/z 252.2 (M+H)+.

Aufarbeitung

temperatureThe reaction mixture was then cooled to ambient temperature
filtrationfiltered through diatomaceous earth
washwhile washing with additional acetone
concentrationconcentrated under reduced pressure
dissolutionThe crude material was then dissolved in a minimal amount of dichloromethane
custompurified via silica gel chromatography
washeluting with a gradient of 80-100% ethyl acetate in heptane

Quellen und Nachweise

ORD-Eintrag: ord-ae4889e1f97041278ba99d4f3d34ae01
Quelldatensatz: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09163007B2

Verknüpfte Notizen

Wird geladen…