Trifluoroacetic acid methylene chloride → 5-Cyclopropyl-7-(((4-phenylpiperidin-4-yl)methoxy)methyl)-1H-indazole

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Reaction Steps

tert-Butyl 4-(((5-cyclopropyl-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-7-yl)methoxy)methyl)-4-phenylpiperidine-1-carboxylate (34 mg, 0.06 mmol) was treated with a trifluoroacetic acid/methylene chloride mixture (1:1, 2 mL) for 4 h. The solvent was removed in vacuo and the resulting crude mixture passed through a strong cation exchange column. After washing the column with several volumes of methanol, the product was eluted by washing the column with 2 M ammonia in methanol. The solvent was evaporated and the product purified by reverse phase HPLC to afford 10 mg (48%) as a clear oil. 1H-NMR (CD3OD, 500 MHz) δ 7.96 (s, 1H), 7.42-7.47 (m, 5H), 7.31-7.34 (m, 1H), 7.01 (m, 1H), 4.71 (s, 2H), 3.51 (s, 2H), 3.24-3.28 (m, 2H), 2.89-2.95 (m, 2H), 2.46-2.49 (m, 2H), 2.16-2.21 (m, 2H), 1.98-2.02 (m, 2H); 13C-NMR (126 MHz, CD3OD) δ ppm 141.1, 138.1, 136.8, 133.5, 129.1, 127.2, 127.0, 125.6, 124.1, 120.1, 116.5, 78.9, 70.4, 41.1, 41.0, 28.9, 15.1, 8.1. Mass spec.: 362.22 (MH)+. Accurate mass spec.: m/z 362.2217 [MH]+, Δ=4.2 ppm.

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