Triphenylphosphine → HCID 89876173, compound

Participants

Reaction Conditions

Reaction Steps

A 3-necked flask is charged with 4-(2,3-dichloroindol-1-yl)-5-methoxy-2-methyl-6-vinyl-pyridazin-3-one (418 mg, 1.19 mmol) and dichlormethane (10 mL). The flask was fitted with a thermometer, an inlet tube and an outlet tube connected to two Dreschel bottles, the latter of which contained a 10% aq. KI solution. The inlet tube was connected to the ozone generator (turned off). The airflow was turned on to give a steady bubbling through the reaction flask and out through the KI solution. The flask was cooled to −78° C. and once at this temperature, the ozone generator was turned on and bubbled for 10 min. The KI solution became darker over the course of the reaction. The ozone generator was turned off and the reaction purged with air for 2 min. It was then disconnected from the inlet and outlet tubes and triphenylphosphine (939 mg, 3.58 mmol) was added. The reaction was allowed to stir and gradually warm to RT over 1 h, then stirred at RT for a further 3 h and left to stand overnight. The resulting reaction mixture was concentrated onto silica and the purified by chromatography (combiflash, 0 to 50% EtOAc/ihexane) to give the desired product 5-(2,3-dichloroindol-1-yl)-4-methoxy-1-methyl-6-oxo-pyridazine-3-carb aldehyde (262 mg, 0.744 mmol, 63%) as a yellow solid.

Provenance & Evidence