Morpholine → HCID 46868294, compound

Participants

Reaction Conditions

Reaction Steps

Add morpholine (3.5 equiv., 25.9 mg, 26.1 μmol, 0.30 mmol) and K2CO3 (11.7 mg, 0.085 mmol) to bisazaindole 32 (54 mg, 0.0848 mmol) in CH3CN (6.0 mL). After heating at 60° C. for 30 h, concentrate the reaction medium under vacuum and submit the residue of raw product to flash chromatography on SiO2 (MeOH at 2-4%/CH2Cl2) to obtain 33 (40 mg, 79.2%) as an ivory-colored solid: 1H NMR (CDCl3) δ 8.26 (d, 1H, J=5.4 Hz), 7.72 (d, 2H, J=8.4 Hz), 7.66 (s, 1H), 7.16 (m, 3H), 7.09 (d, 2H, J=8.1 Hz), 4.29 (t, 2H, J=6.6 Hz), 4.05 (s, 3H), 4.01 (s, 3H), 3.73 (m, 4H), 2.86 (t, 2H, J=6.6 Hz), 2.55 (m, 4H), 2.33 (s, 3H), TLC (MeOH at 4%/CH2Cl2, 0.25% of NH3) Rf=0.25, m/z obs.=597.56 (M+1)

Provenance & Evidence