Water → HCID 22240138, compound

HRID 891948Notes

Reaction equation

HRID 891948 reaction equation
Cl[C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[CH:12][C:11]([F:14])=[C:10]([Cl:15])[CH:9]=2)[N:5]=[N:6][CH:7]=1.C([Sn](CCCC)(CCCC)[CH2:21][O:22][CH2:23][O:24][CH3:25])CCC.C(OCC)(=O)C.O>CN(C=O)C.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Cl:15][C:10]1[CH:9]=[C:8]([C:4]2[N:5]=[N:6][CH:7]=[C:2]([CH2:21][O:22][CH2:23][O:24][CH3:25])[CH:3]=2)[CH:13]=[CH:12][C:11]=1[F:14]

Participants

7

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 4193592Tributyl[(methoxymethoxy)methyl]stannaneHCID 22240223HCID 22240223, compound

Product 1

HCID 22240138HCID 22240138, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

5-Chloro-3-(3-chloro-4-fluoro-phenyl)-pyridazine (535 mg, 2.2 mmol) and bis-(triphenylphosphine) -palladium(II)-dichloride (145 mg, 0.22 mmol) were treated with a solution of tributyl-methoxymethoxymethyl-stannane (Sawyer J. S.; Kucerovy A.; Macdonald T. L.; McGarvey G. J. J. Am. Chem. Soc. (1988), 110, 842-853) (964 mg, 2.64 mmol) in DMF (5.3 ml). The mixture was heated at 100° C. for 4 hours then cooled to room temperature and a saturated KEF solution (5.3 ml) was added. The mixture was stirred for 30 minutes at room temperature and ethyl acetate and water were added. The mixture was filtered and extracted 3 times with ethyl acetate. The combined extracts were dried over Na2SO4, filtered and the solvent was removed in vacuo. The residue was chromatographed over silica gel (hexane-ethylacetate 7:3) to provide 3-(3-chloro-4-fluoro-phenyl)-5-methoxymethoxymethyl-pyridazine (370 mg, 60%) as a pale yellow solid, MS: m/e=283.0 (M+H+).

Workup

  1. temperaturethen cooled to room temperature
  2. filtrationThe mixture was filtered
  3. extractionextracted 3 times with ethyl acetate
  4. dry with materialThe combined extracts were dried over Na2SO4
  5. filtrationfiltered
  6. customthe solvent was removed in vacuo
  7. customThe residue was chromatographed over silica gel (hexane-ethylacetate 7:3)

Sources & evidence

ORD record
ord-7c1241f517294c66b6d7f927a25c434f
Source dataset
uspto-grants-2006_02
Patent number
US07005432B2

Reaction notes

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