Iodine → 7-Benzyl-5-iodo-3-methyl-7,9-dihydro-dipyrido[2,3-b; 4',3'-d]pyrrol-8-one

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Reaction Conditions

Reaction Steps

Compound 28 (2.5 g, 6.93 mmol) dissolved in dry ethanol (200 mL) and stirred under nitrogen at 0° C. Silver tetrafluoroborate (1.45 g, 7.45 mmol) was added, and the solution stirred for 10 minutes. Iodine (1.85 g, 7.3 mmol) was added, and the reaction stirred 1 h as a precipitate began to form. After evaporation of the solvent, the solid was taken up in CH2Cl2 and washed with water, which caused an insoluble precipitate to form. The solid was collected by filtration and washed with ethyl acetate to leave 2.5 g (87%) of intended product. 1H NMR (400 MHz, DMSO-d6): δ 12.74 (s, 1H), 8.69 (s, 1H), 8.42 (s, 1H), 7.90 (s, 1H), 7.25-7.36 (m, 5H), 5.26 (s, 2H), 2.46 (s, 3H). MS (ES) [m+H] calc'd for C18H14IN3O, 416; found 416.

Provenance & Evidence