Methanol → 6-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-pyridazine-3-carboxylic acid methyl ester

HRID 1516204Notes

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]=[CH:18][CH:17]=3)=[N:12][O:13][C:14]=2[CH3:15])=[CH:6][CH:7]=1.[C:22](=[O:25])([O-])[O-:23].[Na+].[Na+].[CH3:28]O>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>[CH3:28][O:23][C:22]([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]=[CH:18][CH:17]=3)=[N:12][O:13][C:14]=2[CH3:15])=[CH:6][CH:7]=1)=[O:25]

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 3-chloro-6-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-pyridazine (2.0 g, 6.6 mmol) in methanol (80 mL) was added sodium carbonate (710 mg, 6.6 mmol), 1,1′-bis(diphenylphosphino)ferrocene (367 mg, 0.6 mmol) and palladium(II) acetate (149 mg, 0.6 mmol). The resulting mixture was stirred at 50° C. overnight under a carbon monoxide atmosphere. After cooling to room temperature it was filtered through Celite® and concentrated. Purification by chromatography (silica, dichloromethane:methanol 1:0 to 9:1) afforded the title compound (960 mg, 40%) as a light brown solid. MS: m/e=326.3 [M+H]+.

Workup

temperatureAfter cooling to room temperature it
filtrationwas filtered through Celite®
concentrationconcentrated
customPurification by chromatography (silica, dichloromethane:methanol 1:0 to 9:1)

Sources & evidence

ORD record: ord-6c1138e1d9484203aeb8008c704f6e89
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08227461B2

Reaction notes

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