5-Bromo-3-pyridinecarboxaldehyde → N-((5-bromopyridin-3-yl)(cyclopropyl)methyl)propane-2-sulfonamide

HRID 391300

Reaktionsgleichung

[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:9]=1)[CH:7]=O.[CH3:10][CH:11]([S:13]([NH2:16])(=[O:15])=[O:14])[CH3:12].[CH:17]1([Mg]Br)[CH2:19][CH2:18]1>C1(C)C=CC=CC=1.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[Br:1][C:2]1[CH:9]=[C:6]([CH:7]([CH:17]2[CH2:19][CH2:18]2)[NH:16][S:13]([CH:11]([CH3:12])[CH3:10])(=[O:15])=[O:14])[CH:5]=[N:4][CH:3]=1

Komponenten

Reaktionsbedingungen

Temperatur: -40 °C

Versuchsvorschrift

A mixture of 5-bromonicotinaldehyde (0.930 g, 5 mmol), propane-2-sulfonamide (0.616 g, 5.00 mmol) and titanium(IV) isopropoxide (2.93 mL, 10.00 mmol) in toluene (20 mL) was heated to reflux for 4 h. After concentration, the residue was dissolved in THF (25 mL) and cooled to −40° C. A solution of cyclopropylmagnesium bromide (25 mL, 12.50 mmol) was added dropwise and the resulting mixture was slowly warmed up to 0° C. over 4 h. After quenching with a NH4Cl solution, filtration and extraction with CH2Cl2, the organic phase was dried over Na2SO4, filtered and concentrated, to give a residue which was purified by flash column (ethyl acetate/heptane, v/v, 10%-35%) and to give a yellow solid (1.1 g). ESI-MS m/z: 335.0 [M+1]+.

Aufarbeitung

temperaturewas heated
temperatureto reflux for 4 h
concentrationAfter concentration
dissolutionthe residue was dissolved in THF (25 mL)
temperaturethe resulting mixture was slowly warmed up to 0° C. over 4 h
customAfter quenching with a NH4Cl solution, filtration and extraction with CH2Cl2
dry with materialthe organic phase was dried over Na2SO4
filtrationfiltered
concentrationconcentrated
customto give a residue which
customwas purified by flash column (ethyl acetate/heptane, v/v, 10%-35%)

Quellen und Nachweise

ORD-Eintrag: ord-8e4e0f0205eb4c91aa016ffcf0ac200e
Quelldatensatz: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08383827B2

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