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

Participants

Reaction Conditions

Reaction Steps

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]+.

Provenance & Evidence