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

HRID 2117330Notes

Reaction equation

HRID 2117330 reaction equation
Cl[C:2]1[CH:7]=[N:6][NH:5][C:4](=[O:8])[CH:3]=1.[CH3:9][O:10][C:11]1[CH:16]=[CH:15][C:14](B(O)O)=[CH:13][CH:12]=1.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>[CH3:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([C:2]2[CH:7]=[N:6][NH:5][C:4](=[O:8])[CH:3]=2)=[CH:13][CH:12]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 201262(4-Methoxyphenyl)boronic acidHCID 199057185-Chloropyridazin-3(2H)-one

Product 1

HCID 135589165-(4-Methoxyphenyl)pyridazin-3(2H)-oneYield 465%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 312751,4-DioxaneSolvent

Procedure

Five reaction tubes each containing 5-chloropyridazin-3(2H)-one (100 mg, 0.77 mmol), 4-methoxyphenylboronic acid (230 mg, 1.53 mmol), dioxane (3 ml), 2M aqueous sodium carbonate solution (1 ml) and [1,1′-bis(diphenylphosphino)ferrocene] dichloropalladium (20 mg) were irradiated in a microwave reactor at 150° C. for 10 minutes. After cooling to room temperature the mixtures were combined and filtered. The collected solid was washed with water (3 ml), ethyl acetate (5 ml) and ether (5 ml), then dried to give the title compound (724 mg, 93%).

Workup

  1. customwere irradiated in a microwave reactor at 150° C. for 10 minutes
  2. filtrationfiltered
  3. washThe collected solid was washed with water (3 ml), ethyl acetate (5 ml) and ether (5 ml)
  4. customdried

Sources & evidence

ORD record
ord-a3b371af3355415f918a8206316f5130
Source dataset
uspto-grants-2008_10
Patent number
US07442701B2

Reaction notes

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