1,10-Phenanthroline → HCID 57721179, 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) (100 mg, 0.32 mmol) in toluene (5 mL) and DME (5 mL), was added the product of Step 1 (128 mg, 0.52 mmol), CuI (62 mg, 0.32 mmol), 1,10-phenanthroline (116 mg, 0.65 mmol), and Cs2CO3 (210 mg, 0.65 mmol). This mixture was then heated to 170° C. by microwave for 40 min. To the reaction mixture was added DMSO (2.0 mL), diluted with EtOAC/MeOH, sonicated for 10 min, then filtered and concentrated. 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 (12.0 mg, 8%). 1H NMR (400 MHz, MeOD) δ ppm 8.71 (d, 1H, 0.8 Hz), 7.35 (t, 1H, 8.0 Hz), 7.19 (d, 1H, 0.8 Hz), 7.10 (d, 1H, 7.6 Hz), 6.94-7.10 (m, 2H), 4.72 (q, 2H, 7.2 Hz), 3.42-3.61 (m, 4H), 2.96 (t, 2H, 7.6 Hz), 2.74 (t, 2H, 7.6 Hz), 2.40-2.48 (m, 4H), 2.35 (s, 3H), 1.46 (t, 3H, 7.2 Hz). MS (ES+) m/e 477 [M+H]+.

Provenance & Evidence