Sodium Carbonate → 5-(4-tert-Butylphenyl)pyridazin-3(2H)-one

HRID 2117326

Reaction equation

Cl[C:2]1[CH:7]=[N:6][NH:5][C:4](=[O:8])[CH:3]=1.[C:9]([C:13]1[CH:18]=[CH:17][C:16](B(O)O)=[CH:15][CH:14]=1)([CH3:12])([CH3:11])[CH3:10].C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].O1CCOCC1>[C:9]([C:13]1[CH:18]=[CH:17][C:16]([C:2]2[CH:7]=[N:6][NH:5][C:4](=[O:8])[CH:3]=2)=[CH:15][CH:14]=1)([CH3:12])([CH3:11])[CH3:10]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 5-chloropyridazin-3(2H)-one (2.94 g, 22.5 mmol), 4-tert-butylphenylboronic acid (8 g, 44.9 mmol), dioxane (100 ml), 2M aqueous sodium carbonate solution (25 ml) and [1,1′-bis(diphenylphosphino)-ferrocene]dichloropalladium (0.5 g) was degassed (N2), then heated at 100° C. for 18 hours under nitrogen. After cooling to room temperature and standing 24 hours, ethyl acetate (250 ml) was added. The mixture was filtered and the collected solid washed with ethyl acetate to give the title compound 2.36 g. The layers of the filtrate were separated, the aqueous phase extracted with ethyl acetate (100 ml) and the combined organic phases evaporated. Ethyl acetate (100 ml) was added to the residue and the mixture left to stand. A second crop of crystals (2.26 g) was collected and washed with ethyl acetate, giving a combined yield of 4.62 g, 90%.

Workup

customwas degassed (N2)
temperatureAfter cooling to room temperature
additionethyl acetate (250 ml) was added
filtrationThe mixture was filtered
washthe collected solid washed with ethyl acetate

Sources & evidence

ORD record: ord-c15581be39c34d18b9460cca805cbd50
Source dataset: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07442701B2

Linked notes

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