Triphenylphosphine → HCID 89876173, compound

HRID 2169769Notes

Reaction equation

HRID 2169769 reaction equation
[Cl:1][C:2]1[N:3]([C:12]2[C:13](=[O:23])[N:14]([CH3:22])[N:15]=[C:16]([CH:20]=C)[C:17]=2[O:18][CH3:19])[C:4]2[C:9]([C:10]=1[Cl:11])=[CH:8][CH:7]=[CH:6][CH:5]=2.[O:24]=[O+][O-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[Cl:1][C:2]1[N:3]([C:12]2[C:13](=[O:23])[N:14]([CH3:22])[N:15]=[C:16]([CH:20]=[O:24])[C:17]=2[O:18][CH3:19])[C:4]2[C:9]([C:10]=1[Cl:11])=[CH:8][CH:7]=[CH:6][CH:5]=2

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 24823Ozone2×HCID 89876194HCID 89876194, compound

Product 1

HCID 89876173HCID 89876173, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

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.

Workup

  1. customThe flask was fitted with a thermometer, an inlet tube and an outlet tube
  2. customto give
  3. customa steady bubbling through the reaction flask and out through the KI solution
  4. custombubbled for 10 min
  5. customThe KI solution became darker over the course of the reaction
  6. customthe reaction purged with air for 2 min
  7. additionwas added
  8. temperaturegradually warm to RT over 1 h
  9. stirringstirred at RT for a further 3 h
  10. waitleft
  11. customThe resulting reaction mixture
  12. concentrationwas concentrated onto silica
  13. customthe purified by chromatography (combiflash, 0 to 50% EtOAc/ihexane)

Sources & evidence

ORD record
ord-e7fd861cce3b4148bb5e512aeedeef22
Source dataset
uspto-grants-2015_06
Patent number
US09049864B2

Reaction notes

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