tert-Butyl 4-(((5-bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazol-7-yl)methoxy)methyl)-4-phenylpiperidine-1-carboxylate → 5-Bromo-7-(((4-phenylpiperidin-4-yl)methoxy)methyl)-1H-indazole

Participants

Reaction Steps

tert-Butyl 4-(((5-bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazol-7-yl)methoxy)methyl)-4-phenylpiperidine-1-carboxylate (40 mg, 0.064 mmol) was dissolved in trifluoroacetic acid (50% in dichloromethane, 3 mL) and stirred at room temperature for 4 h. The reaction was concentrated and loaded onto a strong cation exchange cartridge in methanol. The cartridge was washed with several volumes of methanol which were discarded. The product was eluted with 2 M ammonia in methanol and concentrated. Column chromatography (90:8:4 dichloromethane/methanol/2 M ammonia in methanol) gave 19 mg (75%) as a colorless film. 1H-NMR (CDCl3, 500 MHz) δ 7.87 (s, 1H), 7.74 (d, J=1.8 Hz, 1H), 7.47 (m, 2H), 7.38 (m, 3H), 7.14 (d, J=1.2 Hz, 1H), 4.65 (s, 2H), 3.56 (s, 2H), 2.95 (m, 2H), 2.78 (m, 2H), 2.28 (bs, 1H), 2.22 (m, 2H), 1.88 (m, 2H); 13C-NMR (CDCl3, 126 MHz) δ 143.8, 137.4, 133.6, 129.0, 127.0, 126.8, 125.2, 122.6, 122.5, 113.3, 80.7, 71.7, 42.5, 41.7, 33.5. Mass spec.: 400.01 (MH)+. Accurate mass spec.: m/z 400.1035 [MH]+, Δ=2.6 ppm.

Provenance & Evidence