Sodium Iodide → 1-bromo-3-(4-methoxybenzyl)-7-phenethylpyrazolo[3,4-b]pyrrolo[3,4-d]pyridine-6,8(3H,7H)-dione

Participants

Reaction Steps

To a solution of 1-bromo-7-phenethylpyrazolo[3,4-b]pyrrolo[3,4-d]pyridine-6,8(3H,7H)-dione (500 mg, 1.34 mmol) in anhydrous N,N-dimethylformamide (5 ml), cesium carbonate (2.19 g, 6.7 mmol) and sodium iodide (27 mg, 0.2 mmol) were added followed p-methoxybenzyl chloride (0.18 mL, 2 mmol). The reaction mixture was stirred at room temperature for 2 hours. After completion of reaction (TLC and LCMS), the reaction mixture was poured over ice and extracted with ethyl acetate (3×50 ml). The combined organic layer was dried over sodium sulfate and evaporated under reduced pressure to give a residue which was purified by column chromatography on silica gel using a gradient of 0-20% ethyl acetate-hexanes to afford 1-bromo-3-(4-methoxybenzyl)-7-phenethylpyrazolo[3,4-b]pyrrolo[3,4-d]pyridine-6,8(3H,7H)-dione (400 mg, 60%) as a solid. 1H NMR (400 MHz, CDCl3): δ 9.00 (s, 1H), 7.35 (d, 2H), 7.20-7.30 (m, 5H), 6.80 (d, 2H), 5.70 (s, 2H), 3.95 (t, 2H), 3.80 (s, 3H), 3.00 (t, 2H); LCMS: [M+H] 491.

Provenance & Evidence