Iodine → 6-{[6-(1-Methyl-1H-pyrazol-4-yl)imidazo[1,2-b]pyridazin-3-yl]methyl}quinoline

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Reaction Steps

The title compound was synthesized like described in Tetrahedron Letters, 2001, 42, 831-833): iodine (207 mg, 0.82 mmol) and H3PO2 (0.44 mL of a 50% aqueous solution, 4.07 mmol) were added to a solution of (rac)-[6-(1-methyl-1H-pyrazol-4-yl)-imidazo[1,2-b]pyridazin-3-yl]-quinolin-6-yl-methanol (Example 1, 145 mg, 0.41 mmol) in acetic acid (1 mL). The RM was subjected to MW-irradiation at 150° C. for 30 min. The RM was diluted with water and extracted with EtOAc. The organic layer was separated and washed carefully with sat. K2CO3-sol then dried filtered and concentrated. Purification by HPLC and then liberation of the free base afforded the title compound as a white solid (tR 1.055 min (conditions 1), MH+=341.2, 1H-NMR in DMSO-d6: 8.9 (d, 1H), 8.5 (s, 1H), 8.4 (d, 1H), 8.2 (d, 1H), 8.1 (s, 1H), 8.05 (s, 1H), 8.0 (d, 1H), 7.9 (d, 1H), 7.8 (s, 1H), 7.7 (d, 1H), 7.6 (dd, 1H), 4.6 (s, 2H), 4.0 (s, 3H)).

Provenance & Evidence