Dimethylformamide → 3-ISOPROPYL-[1,2,4]TRIAZOLO[4,3-A]PYRIDINE-6-CARBALDEHYDE

Participants

Reaction Conditions

Reaction Steps

To a stirred, cold (0° C.), dark brown solution of 0.48 g of 6-bromo-3-isopropyl-[1,2,4]triazolo[4,3-a]pyridine in 5 mL of tetrahydrofuran was added slowly 1.3 mL of 2 M isopropylmagnesium chloride in tetrahydrofuran. After 30 minutes N,N-dimethylformamide was added; the ice bath was removed, and the mixture was heated to 50° C. for 150 minutes. The mixture was cooled to 22° C., diluted with 1 M hydrochloric acid, and stirred for 10 minutes. The mixture was made basic with saturated aqueous sodium carbonate, and extracted with ethyl acetate (3×). The combined extracts were washed with brine (2×), dried (sodium sulfate), filtered, and the filtrate was concentrated to give a light yellow solid which was crystallized (ethyl acetate, hexanes, and methanol) to give 0.19 g of 3-isopropyl-[1,2,4]triazolo[4,3-a]pyridine-6-carbaldehyde as a faint yellow solid.

Provenance & Evidence