Morpholine → HCID 46868292, compound

Participants

Reaction Conditions

Reaction Steps

Stir bisazaindole iodide 18 (52 mg, 0.0862 mmol), morpholine (1.10 equiv., 8.26 mg, 8.3 μL, 0.0948 mmol) and K2CO3 (13 mg, 0.0942 mmol), with heating at 60° C. in CH3CN (6 mL) under N2, for 24. LC-MS shows that the reaction is only 50% complete. Add extra morpholine (17 μL) and continue stirring at 60° C. After 48 h, the reaction medium is concentrated under vacuum and the residue is submitted to flash chromatography to give 19 (48 mg, 99%) as a white solid: 1H NMR (CDCl3) δ 8.38 (dd, 1H, J=4.5, 1.2 Hz), 7.75 (dd, 1H, J=4.5, 1.2 Hz), 7.68 (d, 2H, J=8.4 Hz), 7.62 (s, 1H), 7.14 (m, 2H), 7.05 (d, 2H, J=8.4 Hz), 7.02 (s, 1H), 4.28 (t, 2H), 4.05 (s, 3H), 4.0 (s, 3H), 3.74 (m, 4H), 2.90 (t, 2H), 2.55 (m, 4H), 2.29 (s, 3H). TLC (MeOH at 4%/CH2Cl2, 0.25% of NH3) Rf=0.65, m/z obs.=562.15 (M+1)

Provenance & Evidence