Water → HCID 117833194, compound

HRID 2169764Notes

Reaction equation

HRID 2169764 reaction equation
ClC1N([C:12]2[C:13](=O)[N:14]([CH3:23])[N:15]=[C:16]([C:20]([CH3:22])=[CH2:21])[C:17]=2[O:18][CH3:19])C2C(C=1Cl)=CC=CC=2.C([O-])=O.[NH4+:28].[OH2:29].N1(C2C(=O)N(C)N=C(C(C)C)C=2OC)[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH:32]=[CH:31]1>C(O)C.[OH-].[OH-].[Pd+2]>[N:28]1([C:17]2([O:18][CH3:19])[C:16]([CH:20]([CH3:22])[CH3:21])=[N:15][N:14]([CH3:23])[C:13](=[O:29])[CH2:12]2)[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH:32]=[CH:31]1

Participants

7

Reactant 4

HCID 962WaterHCID 2723923Ammonium formateHCID 89876220HCID 89876220, compoundHCID 117833358HCID 117833358, compound

Product 1

HCID 117833194HCID 117833194, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

To a stirred solution of 4-(2,3-dichloroindol-1-yl)-6-isopropenyl-5-methoxy-2-methyl-pyridazin-3-one (355 mg, 0.975 mmol) in ethanol (5.0 mL) is added ammonium formate (1.24 g) and 20% palladium hydroxide on carbon, (50% water by weight, 273 mg, 0194 mmol). The resulting reaction mixture is stirred at ambient temperature for 1 h and then heated to 60° C. for 30 min. The resulting reaction mixture is allowed to cool and then filtered through celite, washing with ethanol and concentrated in vacuo. The resulting crude yellow solid was 4-indol-1-yl-6-isopropyl-5-methoxy-2-methyl-pyridazin-3-one (253 mg, 0.851 mmol, 87%), which was used without further purification.

Workup

  1. customThe resulting reaction mixture
  2. temperatureheated to 60° C. for 30 min
  3. customThe resulting reaction mixture
  4. temperatureto cool
  5. filtrationfiltered through celite
  6. washwashing with ethanol
  7. concentrationconcentrated in vacuo
  8. customwas used without further purification

Sources & evidence

ORD record
ord-31ab859e7ea04841b2f8832b9ed3782b
Source dataset
uspto-grants-2015_06
Patent number
US09049864B2

Reaction notes

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