Methanol → (5-Bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazol-7-yl)methanol

Participants

Reaction Steps

To a solution of (5-bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazol-7-yl)methyl acetate (1.04 g, 2.60 mmol) in methanol (15 mL, 371 mmol) at room temperature was added potassium carbonate (200 mg, 1.45 mmol). After 20 min, the reaction was concentrated and the resulting residue partitioned between water and diethyl ether. The ethereal was washed with water (2×), then brine, dried over magnesium sulfate, and concentrated. Column chromatography (12%→25% EtOAc/Hex) gave 0.73 g (78%) as a colorless oil that solidified to an amorphous white solid upon standing. 1H-NMR (CDCl3, 500 MHz) δ 7.91 (s, 1H), 7.81 (d, J=1.5, 1H), 7.43 (d, J=1.8, 1H), 5.90 (s, 2H), 4.97 (d, J=6.4, 2H), 3.49 (m, 2H), 3.43 (t, J=6.4, 1H), 0.83 (m, 2H), −0.09 (s, 9H); 13C NMR(126 MHz, CDCl3) δ ppm 136.7, 133.5, 131.1, 128.1, 125.9, 123.6, 114.4, 80.0, 66.6, 62.5, 17.8, −1.4.

Provenance & Evidence