Stannous Chloride → HCID 44546126, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of 6-(2-(4-chloro-3-nitrobenzyl)-5-(6-methylpyridin-2-yl)-1H-imidazol-4-yl)quinoline (Example 74, prepared according to the method described in US 2008/0319012 A1) (50 mg, 0.110 mmol) in MeOH (2 mL) was added SnCl2 (104 mg, 0.548 mmol) and the mixture was stirred at 55° C. After 2.5 hours, the reaction mixture was cooled to room temperature, concentrated under reduced pressure. The residue was diluted with H2O (5 mL), filtered, and the filtrate was washed with 2N HCl (5 mL) and neutralized by addition of 5N NaOH solution to pH 7˜8. The precipitate was filtered, washed with H2O and Et2O, and dried under vacuum for overnight. The precipitate was purified by MPLC on silica gel (MeOH:EA:CH2Cl2=1:20:80 (v/v) to 1:4:16 (v/v)), and on NH silica gel (MC) to afford the title compound (33.1 mg, 71%). 1H NMR (300 MHz, CDCl3) δ 2.50 (3H, s), 4.09 (2H, s), 6.66 (1H, dd), 6.68 (1H, s), 6.96 (1H, d), 7.19 (1H, d), 7.25 (1H, bs), 7.36-7.39 (1H, m), 7.40 (1H, dd), 7.96 (1H, d), 8.10 (1H, d), 8.15-8.16 (2H, m), 8.91 (1H, dd). MS (ESI) m/z 426 (MH+).

Provenance & Evidence