1-(5-(2H-1,2,3,4-Tetrazol-5-Yl)(1H-Indazol-3-Yl))-2-Methoxybenzene → 2-(5-(2h-1,2,3,4-Tetrazol-5-yl)-1h-indazol-3-yl)phenol

Participants

Reaction Steps

The compound of Example 161 (0.050 g, 0.17 mmol) was suspended in 1 mL of boron tribromide (1.0 M commercial solution in dichloromethane). The reaction mixture was stirred at room temperature in a closed system for 4 days to achieve completion. The product was then collected by filtration and washed with small portions of dichloromethane. Trituration in a few mL of tetrahydrofuran and filtration did not afford satisfactory purity. Final purification by preparative HPLC (30-80% acetonitrile in water, 20 mm) afforded 3 mg of pure product. (6% yield): 1H NMR (DMSO-d6) δ 13.6 (s, 1H), 10.3 (s, 1H), 8.7 (s, 1H), 8.1 (d, 1H), 7.8 (t, 2H), 7.3 (t, 1H), 7.08-7.00 (m, 2H); ES-MS (m/z) 279 [M+1]+.

Provenance & Evidence