Sodium Iodide → 6-(4-(4-(2,3-dichlorophenyl)piperidin-1-yl)butoxy)-1H-indazole

Participants

Reaction Steps

A mixture of intermediate 51 (40.6 mg, 0.15 mmol) and NaI (45.2 mg, 0.30 mmol) in CH3CN (3 mL) was heated to reflux for 30 min and then cooled to rt. To this mixture was added intermediate 47 (60.3 mg, 0.23 mmol), followed then by DIEA (0.058 mL, 0.33 mmol). The resulting mixture was heated to reflux and stirred for 4 h. Precipitated crystals were filtered off and the filtrate was evaporated under reduced pressure. The residue was extracted with EtOAc. The combined EtOAc layers were washed with brine, dried over anhydrous Na2SO4, concentrated in vacuo and purified by ISCO to give 6-(4-(4-(2,3-dichlorophenyl)piperidin-1-yl)butoxy)-1H-indazole (compound 45) (37.6 mg, 60%). 1H NMR (400 MHz, CDCl3): δ 7.93 (s, 1H), 7.54 (d, J=8.8 Hz, 1H), 7.33 (dd, J=7.9, 1.2 Hz, 1H), 7.25-7.20 (m, 1H), 7.15 (t, J=7.9 Hz, 1H), 6.93 (s, 1H), 6.74 (dd, J=8.8, 1.9 Hz, 1H), 3.94 (t, J=6.0 Hz, 2H), 3.75-3.67 (m, 2H), 3.46-3.36 (m, 1H), 3.15-3.08 (m, 2H), 3.03-2.91 (m, 2H), 2.59-2.43 (m, 2H), 2.18-2.06 (m, 2H), 2.06-1.96 (m, 2H), 1.88-1.75 (m, 2H). HPLC: 99%, RT 4.447 min. MS (ESI) m/z 418.10 [M+H]+.

Provenance & Evidence