Ethanol → HCID 42630253, compound

HRID 548852Notes

Reaction equation

HRID 548852 reaction equation
Cl[C:2]1[N:3]=[N:4][C:5]([O:8][CH2:9][C:10]2[C:11]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[CH:17]=3)=[N:12][O:13][C:14]=2[CH3:15])=[CH:6][CH:7]=1.[C:23](=[O:26])([O-])[O-:24].[Na+].[Na+].[CH2:29](O)[CH3:30]>C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:29]([O:24][C:23]([C:2]1[N:3]=[N:4][C:5]([O:8][CH2:9][C:10]2[C:11]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[CH:17]=3)=[N:12][O:13][C:14]=2[CH3:15])=[CH:6][CH:7]=1)=[O:26])[CH3:30]

Participants

6

Reactant 3

HCID 702Ethanol2×HCID 10340Sodium CarbonateHCID 86630895HCID 86630895, compound

Product 1

HCID 42630253HCID 42630253, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)Catalyst

Conditions

Temperature
50 °C

Procedure

To a solution of 3-chloro-6-[3-(3-fluoro-phenyl)-5-methyl-isoxazol-4-ylmethoxy]-pyridazine (4.1 g, 13 mmol) in ethanol (65 mL) was added sodium carbonate (1.37 g, 13 mmol), 1,1′-bis(diphenylphosphino)ferrocene (716 mg, 1.3 mmol) and palladium(II) acetate (290 mg, 1.3 mmol). The resulting mixture was heated at 50° C. overnight under a carbon monoxide atmosphere. After cooling to room temperature the mixture was diluted with ethanol (100 mL), filtered through Celite® and concentrated. Purification by chromatography (SiO2, heptane:ethyl acetate=100:0 to 1:1) afforded the title compound (3.2 g, 70%) as an off white solid. MS: m/e=358.0 [M+H]−.

Workup

  1. temperatureAfter cooling to room temperature the mixture
  2. filtrationfiltered through Celite®
  3. concentrationconcentrated
  4. customPurification by chromatography (SiO2, heptane:ethyl acetate=100:0 to 1:1)

Sources & evidence

ORD record
ord-7344f44e07304fc197ce070f25c1b79a
Source dataset
uspto-grants-2011_05
Patent number
US07943619B2

Reaction notes

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