Ethanol → 6-(3-Butyl-5-methyl-isoxazol-4-ylmethoxy)-pyridazine-3-carboxylic acid ethyl ester

HRID 1958075Notes

Reaction equation

[CH2:1]([C:5]1[C:9]([CH2:10][O:11][C:12]2[N:13]=[N:14][C:15](Cl)=[CH:16][CH:17]=2)=[C:8]([CH3:19])[O:7][N:6]=1)[CH2:2][CH2:3][CH3:4].[C:20](=[O:23])([O-])[O-:21].[Na+].[Na+].[CH2:26](O)[CH3:27]>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>[CH2:26]([O:21][C:20]([C:15]1[N:14]=[N:13][C:12]([O:11][CH2:10][C:9]2[C:5]([CH2:1][CH2:2][CH2:3][CH3:4])=[N:6][O:7][C:8]=2[CH3:19])=[CH:17][CH:16]=1)=[O:23])[CH3:27]

Participants

Conditions

Temperature: 50 °C

Procedure

A suspension of 3-(3-butyl-5-methyl-isoxazol-4-ylmethoxy)-6-chloro-pyridazine (1.2 g, 3.6 mmol) and sodium carbonate (379 mg, 3.6 mmol) in ethanol (20 mL) was evacuated and filled with argon five times. 1,1′-Bis(diphenylphosphino)ferrocene (198 mg, 3.6 mmol) and palladium(II) acetate (80 mg, 0.36 mmol) were added then the flask was evacuated again and filled with carbon monoxide. The reaction mixture was then heated to 50° C. After 15 h the reaction mixture was cooled, filtered through decalite and evaporated. The residue was purified by chromatography (silica, 0 to 50% ethyl acetate in heptane) to give the title compound (1.0 g, 88%) as a light yellow oil. MS: m/e=320.2 [M+H]+.

Workup

customwas evacuated
additionfilled with argon five times
customthe flask was evacuated again
additionfilled with carbon monoxide
temperatureAfter 15 h the reaction mixture was cooled
filtrationfiltered through decalite
customevaporated
customThe residue was purified by chromatography (silica, 0 to 50% ethyl acetate in heptane)

Sources & evidence

ORD record: ord-0b3fdf0604c04c9b856d069e84307171
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08410104B2

Reaction notes

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