Pyruvic Acid → HCID 118275230, compound

Participants

Reaction Conditions

Reaction Steps

Under argon, pyruvic acid (6.90 ml, 100.1 mmol) and 1,4-diazabicyclo[2.2.2]octane (843 g, 7.51 mmol) were added to a solution of tert-butyl [(6-amino-5-iodo-2-methylpyridin-3-yl)methyl]carbamate (840 mg, 2.31 mmol) in N,N-dimethylformamide (0.5 ml), and the flask was evacuated and flushed with argon. Then argon was passed through the solution for 5 min and then palladium(II) acetate (25.9 mg, 0.11 mmol) was added and the mixture was heated to 100° C. for 2 h. The cooled solution was filtered through Celite and the dimethylformamide was distilled off. The residue was then taken up in water and acidified with hydrochloric acid, giving a 5-{[(tert-butoxycarbonyl)amino]methyl}-6-methyl-1H-pyrrolo[2,3-b]pyridine-2-carboxylic acid (650 g, 88% of theory). HPLC-MS: log P=0.58; mass (m/z): 306.1 (M+H)+; 1H-NMR (DMSO) 1.37 (s, 9H), 2.33 (s, 3H), 4.17 (d, 2H), 6.57 (s, 1H), 7.68 (s, 1H).

Provenance & Evidence