Water → HCID 86684818, compound

HRID 1527985Notes

Reaction equation

HRID 1527985 reaction equation
O.[Br:2][C:3]1[CH:8]=[CH:7][C:6]([C@@H:9]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[CH3:28])[CH2:10][C:11]([C:13]2[N+:18]([O-])=[N:17][C:16]([O:20][CH3:21])=[CH:15][CH:14]=2)=[O:12])=[CH:5][CH:4]=1>C1COCC1.[Mo](Cl)(Cl)(Cl)(Cl)Cl.[Zn]>[Br:2][C:3]1[CH:8]=[CH:7][C:6]([C@@H:9]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[CH3:28])[CH2:10][C:11]([C:13]2[N:18]=[N:17][C:16]([O:20][CH3:21])=[CH:15][CH:14]=2)=[O:12])=[CH:5][CH:4]=1

Participants

6

Reactant 2

HCID 962WaterHCID 86684819HCID 86684819, compound

Product 1

HCID 86684818HCID 86684818, compoundYield 38.1%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 61497Molybdenum pentachlorideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Water (0.2 mL) was added to a suspension of molybdenum(V) chloride (160 mg, 0.56 mmol) in THF (1 mL), then after 5 min zinc dust (60 mg, 0.92 mmol) was added portionwise, followed by (S)-6-(3-(4-bromophenyl)-3-o-tolylpropanoyl)-3-methoxypyridazine 1-oxide (100 mg, 0.23 mmol). The mixture was heated at reflux for 90 min, then partitioned between water and ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate, filtered, and evaporated in vacuo. Chromatography (SiO2; heptane-ethyl acetate gradient) afforded the title compound (36 mg, 38%). Colorless gum, MS: 411.2 [M+H]+.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 90 min
  3. custompartitioned between water and ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-24b9539e5d3d4250ad32e997643069b4
Source dataset
uspto-grants-2015_07
Patent number
US09090565B2

Reaction notes

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