Methanol → 6-[(5-Methyl-3-phenyl-isoxazol-4-ylmethyl)-amino]-pyridazine-3-carboxylic acid methyl ester

HRID 548874Notes

Reaction equation

I[C:2]1[N:7]=[N:6][C:5]([NH: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:4][CH:3]=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:7]=[N:6][C:5]([NH: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:4][CH:3]=1)=[O:25]

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of (6-iodo-pyridazine-3-yl)-(5-methyl-3-phenyl-isoxazol-4ylmethyl)-amine (1.0 g, 2.6 mmol) in methanol (3 mL) was added sodium carbonate (270 mg, 2.6 mmol), 1,1′-bis(diphenylphosphino)ferrocene (141 mg, 0.26 mmol) and palladium(II) acetate (57 mg, 0.26 mmol). The resulting mixture was heated at 50° C. for 16 h under a carbon monoxide atmosphere. After cooling to room temperature it was filtered through Celite® and concentrated. Purification by chromatography (SiO2, heptane:ethyl acetate=100:0 to 20:80) afforded the title compound (720 mg, 87%) as a light brown solid. MS: m/e=325.3 [M+H]+.

Workup

temperatureAfter cooling to room temperature it
filtrationwas filtered through Celite®
concentrationconcentrated
customPurification by chromatography (SiO2, heptane:ethyl acetate=100:0 to 20:80)

Sources & evidence

ORD record: ord-9130a190beaa43d5b79b27512e2dedaa
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07943619B2

Reaction notes

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