Sodium Iodide → 2-[4-(3-Pyrrolidin-1-ylpropoxy)phenyl]-2h-indazole

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-Indazol-2-ylphenol (28 mg, 0.13 mmol) and sodium iodide (6 mg, 0.04 mmol) in N,N-dimethylformamide (3 mL) was added sodium hydride (8.0 mg, 60% in mineral oil, 0.2 mmol) followed by 1-(3-chloropropyl)pyrrolidine (30 mg, 0.20 mmol). After the reaction was heated at 85° C. overnight and allowed to cool, it was partitioned between water and methylene chloride. The organic layer was dried (MgSO4), concentrated and purified by semi-prep LC-MS to give 5.0 mg of the desired indazole. LC-MS (C20H23N3O calc'd 321) m/z 322 (M+H); 1H NMR (300 MHz, CDCl3) δ 8.33 (s, 1H), 7.81-7.77 (m, 3H), 7.71 (d, J=8.7 Hz, 1H), 7.34-7.29 (m, 1H), 7.14-7.09 (m, 1H), 7.05-7.02 (m, 2H), 4.10 (t, J=6.6 Hz, 2H), 2.72 (t, J=7.2 Hz, 2H), 2.63 (m, 4H), 2.08 (quint, J=6.3 Hz, 2H), 1.86-1.81 (m, 4H).

Provenance & Evidence