Ethanol → 6-Iodo-3-[3-(2-morpholin-4-yl-ethoxy)-phenyl]-[1,2,4]triazolo[4,3-a]pyridine

To a solution of Example 1 step a (10.93 g, 24.16 mmol) in DCM (100 mL)/EtOH (15 mL), was added Phl(OAc)2 (10.74 g, 33.35 mmol). The reaction was stirred at RT for 72 h, diluted with DCM (25 mL) then washed with aq. sodium hydroxide (1 M, 25 mL) and brine (25 mL). The organic layer was dried (MgSO4), filtered, and the filtrate was concentrated in vacuo. The residue was triturated with Et2O (10 mL) and the resulting solid was collected by filtration to afford the title compound (9.98 g, 92%) as an off-white solid. LCMS (Method 1): Rt 2.11 min, m/z 451 [MH+]. 1H NMR (400 MHz, DMSO-d6): δ 8.69 (1 H, s), 7.71 (1 H, d, J 9.5), 7.60 (1 H, d, J 9.5), 7.53 (1 H, t, J 7.9), 7.47-7.41 (2 H, m), 7.18 (1 H, d, J 8.1), 4.21 (2 H, t, J 5.7), 3.59 (4 H, t, J 4.5), 2.75 (2 H, t, J 5.7), 2.45 (4 H, m).

1. washthen washed with aq. sodium hydroxide (1 M, 25 mL) and brine (25 mL)
2. dry with materialThe organic layer was dried (MgSO4)
3. filtrationfiltered
4. concentrationthe filtrate was concentrated in vacuo
5. customThe residue was triturated with Et2O (10 mL)
6. filtrationthe resulting solid was collected by filtration

ORD-Eintrag

ord-16b67d99f3e24b36bf0a39d0915bf042

Quelldatensatz

uspto-grants-2013_10

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08557797B2