Potassium Hydroxide → (6-Methoxy-pyrazolo[1,5-b]pyridazin-3-yl)-(3,4,5-trimethoxy-phenyl)-methanone

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Reaction Conditions

Reaction Steps

Potassium bicarbonate (2.5 M) was added to a solution of hydroxylamine-O-sulfonic acid (64.7 mg, 0.57 mmol) until the pH value turned to 5. Then, 3-methoxypyridazine (42 mg, 0.38 mmol) was added at 70° C. over 10 min. The mixture was stirred at 70° C. for 2 h and then cooled to room temperature. The pH value of the mixture was adjusted to 8 by addition of 2.5M potassium bicarbonate. 1-(3,4,5-Trimethoxyphenyl)prop-2-yn-1-one (42 mg, 0.19 mmol) in CH2Cl2 (10 mL) and potassium hydroxide (40 mg, 0.71 mmol) were added. The mixture was stirred at room temperature overnight, and then was extracted with CH2Cl2, and the combined organic layers were washed with brine, dried over MgSO4, and concentrated to give a crude product, which was purified on a silica gel column eluting with CH2Cl2/MeOH (20:1) to afford compound 15 as a white solid (31 mg, 48%).

Provenance & Evidence