Sodium hydride → HCID 57581128, compound

Participants

Reaction Steps

5-bromo-3-(4-methoxymethyl-1H-benzoimidazol-2-yl)-1H-pyrazolo[3,4-b]pyridine Compound 11 (1.2 g, 4.19 mmol) was dissolved in dry THF (20 mL). The solution was cooled to 0° C. before sodium hydride (0.37 g, 60% in mineral oil, 9.25 mmol) was added in portions. The suspension was stirred at 0° C. for additional 15 minutes before (trimethylsilyl)ethoxymethyl chloride (1.78 mL, 10.06 mmol) was added. The reaction was warmed to room temperature and stirred overnight. Solvent was removed and the residue was purified by silica gel chromatography (10% to 50% ethyl acetate in hexanes) to yield 5-bromo-3-[4-methoxymethyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-benzoimidazol-2-yl]-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-b]pyridine Compound 12a (1.59 g, 77%) as amber oil. 1H NMR (300 MHz, CDCl3) δ 9.35 (d, 1H, J=2.4 Hz), 8.84 (d, 1H, J=2.4 Hz), 7.74 (d, 1H, J=5.4 Hz), 7.57 (m, 2H), 6.45 (s, 2H), 6.09 (s, 2H), 5.26 (s, 2H), 3.86 (m, 4H), 3.77 (s, 3H), 1.13 (t, 2H, J=7.2 Hz), 1.05 (t, 2H, J=7.8 Hz), 0.14 (s, 9H), 0.03 (s, 9H); MS (ESI) m/z: 619 (M+H+).

Provenance & Evidence