Sodium periodate → HCID 118081840, compound

Participants

Reaction Steps

The crude 4-(hydroxymethyl)-6-[4-methyl-2-(3-pyridyl)thiazol-5-yl]-2,3-dihydropyrano[3,2-b]pyridin-4-ol from step e was dissolved in a 1:1 mixture of dioxane (40 mL) and H2O (40 mL), and sodium periodate (2.22 g, 10.76 mmol) was added. The reaction mixture was stirred at ambient temperature for 1 h. The reaction mixture was diluted with dichloromethane (50 mL) and H2O (50 mL) and the two layers were separated. The organic layer was dried over Na2SO4, filtered and concentrated. The resulting residue was purified by silica gel chromatography (CH2Cl2/MeOH=100/1) to afford the title compound as a yellow solid (1.7 g, two-step yield: 48%). 1H NMR (400 Mz, CDCl3): 2.76 (s, 3H); 3.02 (t, J=6.6, 2H); 4.66 (t, J=6.9, 2H); 7.49 (d, J=9, 1 H); 7.62-7.58 (m, 1H); 7.75 (d, J=8.7, 1 H); 8.45 (d, J=7.8, 1 H); 8.71 (d, J=3.9, 1H); 9.28 (s, 1H).

Provenance & Evidence