Carbon tetrabromide → HCID 57546133, compound

Participants

Reaction Steps

To a solution of (±)-1-(5-(trifluoromethyl)-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-7-yl)ethanol (444 mg, 1.23 mmol) and carbon tetrabromide (613 mg, 1.85 mmol) in tetrahydrofuran (5 mL) at 0° C. was added triphenylphosphine (485 mg, 1.85 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%→6% EtOAc/Hex) to give 284 mg (55%) as a colorless oil. 1H-NMR (CDCl3, 500 MHz) δ 8.27 (s, 1H), 8.00 (s, 1H), 7.58 (s, 1H), 5.90 (q, J=7.0 Hz, 1H), 5.77 (qAB, JAB=10.4 Hz, 2H), 3.68 (m, 2H), 2.23 (d, J=7.0 Hz, 3H), 0.95 (m, 2H), −0.03 (s, 9H); 13C-NMR (CDCl3, 126 MHz) δ 146.4, 134.2, 124.9, 124.7 (q, J=32 Hz), 124.6 (q, J=273 Hz), 121.6, 119.7 (q, J=4.8 Hz), 119.3 (q, J=2.9 Hz), 82.2, 68.1, 43.7, 25.5, 18.0, −1.4.

Provenance & Evidence