1,1'-Carbonyldiimidazole → HCID 178461348, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 6-bromopicolinic acid acid (3 g, 14.85 mmol), and 1,1′-carbonyldiimidazole (2.41 g, 14.85 mmol) in dimethylformamide (30 mL) was heated at 50° C. for 2 hours. After this time, trans-4-methylcyclohexylamine hydrochloride (2.2 g, 14.85 mmol), and N,N-diisopropylethylamine (3.88 mL, 22.3 mmol) were added and the mixture heated at 50° C. for 16 hours. The reaction mixture was cooled, and diluted with ethyl acetate (300 mL). The organic solution was washed with water (4×300 mL). The aqueous extracts were washed with ethyl acetate (2×250 mL). The combined organic extracts were dried over anhydrous MgSO4, filtered and concentrated. Chromatography of the crude product through a Biotage silica cartridge (15×4 cm i.d.) using ethyl acetate-hexane (1:3, containing 1% diethylamine) afforded 3.84 g (87%) of 409:

Provenance & Evidence