1,10-Phenanthroline → HCID 68873842, compound

Participants

Reaction Conditions

Reaction Steps

Under argon, to a suspension of 4-(6-bromo-1-ethyl-1H-imidazo[4,5-c]pyridin-2-yl)-furazan-3-amine (prepared by the method of Example 8, Steps 3-7, substituting ethylamine for aniline in Step 3) (80 mg, 0.26 mmol) in toluene (4 mL) and DME (4 mL), was added the product of Step 2 (88 mg, 0.31 mmol), CuI (50 mg, 0.26 mmol), 1,10-phenanthroline (94 mg, 0.52 mmol), and Cs2CO3 (170 mg, 0.52 mmol). This mixture was then heated to 170° C. by microwave for 15 min. To the reaction mixture was added DMSO (2.0 mL), diluted with EtOAC/MeOH, sonicated for 10 min, then filtered and concentrated. The residue was purified with reverse phase HPLC (10% MeCN/H2O→80% MeCN/H2O, containing 0.1% TFA), to afford the title compound as a pale yellow solid (72.0 mg, 46%). 1H NMR (400 MHz, DMSO) δ ppm 9.71 (bs, 1H), 8.77 (d, 1H, 0.8 Hz), 7.84 (d, 1H, 8.0 Hz), 7.69 (t, 1H, 2 Hz), 7.59-7.64 (m, 2H), 7.45 (dd, 1H, 8 Hz, 0.8 Hz), 6.96 (s, 2H), 4.70 (q, 2H, 7.2 Hz), 3.98 (d, 2H, 12.4 Hz), 3.60-3.81 (m, 2H), 3.42-3.47 (m, 2H), 3.01-3.19 (m, 4H), 1.96-2.01 (m, 1H), 1.41 (t, 3H, 7.2 Hz), 1.38 (d, 3H, 10.4 Hz). MS (ES+) m/e 492 [M+H]+.

Provenance & Evidence