Carbon tetrabromide → 7-(Bromomethyl)-5-(trifluoromethyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazole

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To a solution of (5-(trifluoromethyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazol-7-yl)methanol (980 mg, 2.83 mmol) and carbon tetrabromide (1.41 g, 4.24 mmol) in tetrahydrofuran (10 mL) at 0° C. was added triphenylphosphine (1.11 g, 4.24 mmol). The resulting solution was stirred at room temperature for 30 min. The reaction was diluted with several volumes of pentane and filtered to remove undissolved solids. The organics were concentrated and purified by column chromatography (4%→8% EtOAc/Hex) to give 1.155 g (100%) as a colorless oil. 1H-NMR (CDCl3, 500 MHz) δ 8.12 (s, 1H), 8.03 (s, 1H), 7.61 (d, J=1.2 Hz, 1H), 6.05 (s, 2H), 5.01 (s, 2H), 3.52 (m, 2H), 0.87 (m, 2H), −0.08 (s, 9H); 13C-NMR (CDCl3, 126 MHz) δ 138.4, 135.1, 126.4, 125.7, 124.4 (q, J=33 Hz), 124.3 (q, J=273 Hz), 122.5, 120.1, 80.5, 66.6, 29.7, 17.9, −1.4.

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