Sodium Iodide → HCID 89586444, compound

HRID 1747837Notes

Reaction equation

HRID 1747837 reaction equation
[CH3:1][O:2][C:3]1[C:4]([OH:20])=[C:5]([C:9]2[N:13]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[N:12]=[CH:11][CH:10]=2)[N:6]=[N:7][CH:8]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH:28]1[CH2:30][CH2:29]1.[I-].[Na+]>CN(C=O)C.O>[CH:28]1([N:7]2[CH:8]=[C:3]([O:2][CH3:1])[C:4](=[O:20])[C:5]([C:9]3[N:13]([C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=4)[N:12]=[CH:11][CH:10]=3)=[N:6]2)[CH2:30][CH2:29]1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 10796Cesium carbonateHCID 78037BromocyclopropaneHCID 178493808HCID 178493808, compound

Product 1

HCID 89586444HCID 89586444, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

To a solution of 5-methoxy-3-(1-phenyl-1H-pyrazol-5-yl)pyridazin-4-ol (1.0 g) in DMF (20 ml) were added cesium carbonate (2.429 g), bromocyclopropane (0.597 ml) and sodium iodide (0.559 g) at room temperature. The reaction mixture was stirred at 150° C. for 30 hr in an autoclave, allowed to cool to room temperature, and poured into water (100 ml). The mixture was extracted with ethyl acetate, the organic layer was washed with saturated brine, dried over magnesium sulfate, and concentrated to dryness under reduced pressure. The residue was purified by silica gel column chromatography (methanol/ethyl acetate). The fraction containing the title compound was purified again by silica gel column chromatography (NH, methanol/ethyl acetate), and crystallized from methanol/ethyl acetate to give the title compound (15 mg).

Workup

  1. temperatureto cool to room temperature
  2. extractionThe mixture was extracted with ethyl acetate
  3. washthe organic layer was washed with saturated brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated to dryness under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (methanol/ethyl acetate)
  7. additionThe fraction containing the title compound
  8. customwas purified again by silica gel column chromatography (NH, methanol/ethyl acetate)
  9. customcrystallized from methanol/ethyl acetate

Sources & evidence

ORD record
ord-14385af22bea48b5adc452b665fa841a
Source dataset
uspto-grants-2015_10
Patent number
US09150588B2

Reaction notes

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