Acetic Acid → 2-[6-(Thiazolo[4,5-b]pyridin-2-yloxy)-1H-indol-3-ylmethyl]-1,2,3,4-tetrahydro-benzo[4,5]thieno[3,2-c]pyridine formate

Participants

Reaction Conditions

Reaction Steps

To a solution of thiazolo[4,5-b]pyridine (50 mg, 0.19 mmol) in dioxane (0.9 mL) was added 1,2,3,4-tetrahydro-benzo[4,5]thieno[3,2-c]pyridine (35 mg, 0.19 mmol), formaldehyde (35% wt in water, 14 μL, 15 mg, 0.19 mmol) and acetic acid (0.9 mL). The reaction mixture was heated (50° C., 16 h). The reaction mixture was cooled (rt) and concentrated in vacuo. The resulting residue was purified reverse phase HPLC to provide the title compound as a white solid (49 mg, 56%). MS (ESI): mass calcd. for C26H20N4OS2, 468.1; m/z found, 469.1 [M+H]+. 1H NMR (500 MHz, CD3OD): 8.49 (dd, J=4.9, 1.6, 1H), 8.25 (dd, J=8.0, 1.6, 1H), 7.86 (d, J=8.6, 1H), 7.78 (d, J=7.8, 1H), 7.51 (d, J=7.9, 1H), 7.49-7.44 (m, 2H), 7.36-7.30 (m, 2H), 7.30-7.24 (m, 1H), 7.11 (dd, J=8.6, 2.2, 1H), 4.08 (s, 2H), 3.84 (s, 2H), 3.07-2.92 (m, 4H).

Provenance & Evidence