2-Bromo-1,1-dimethoxyethane → 3-Bromo-7-chloro-1,6-naphthyridine

Participants

Reaction Steps

Heat a mixture of 4-amino-6-chloronicotinaldehyde (2.00 g, 12.77 mmol), 2-bromo-1,1-dimethoxyethane (6.48 g, 38.3 mmol) and ytterbium(III) trifluoromethanesulfonate (1.981 g, 3.19 mmol) in MeCN (25 mL) at 80° C. overnight. Cool to RT, dilute with EtOAc, collect the solids via filtration, rinse with EtOAc and dry. Wash the filtrate with H2O, then brine, dry over Na2SO4, concentrate to dryness and purify via silica gel chromatography (EtOAc/Hex). Combine the two solids to afford the title compound (1.67 g, 53%) as an off-white solid. MS(ESI) m/z: 244.9 (M+H+).

Provenance & Evidence