Water → 3-(2,4-Dimethylphenyl)-1-methyl-5-nitropyridin-2(1H)-one

HRID 598053Notes

Reaction equation

Br[C:2]1[C:3](=[O:12])[N:4]([CH3:11])[CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1.[CH3:13][C:14]1[CH:19]=[C:18]([CH3:20])[CH:17]=[CH:16][C:15]=1B(O)O.C(=O)([O-])[O-].[K+].[K+].O>O1CCOCC1.C(OCC)(=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:13][C:14]1[CH:19]=[C:18]([CH3:20])[CH:17]=[CH:16][C:15]=1[C:2]1[C:3](=[O:12])[N:4]([CH3:11])[CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture containing 0.40 g (1.72 mmol) of 3-bromo-1-methyl-5-nitropyridin-2(1H)-one, 0.39 g (2.60 mmol) of 2,4-dimethylphenyl boronic acid, 0.70 g (5.06 mmol) of potassium carbonate, 0.31 ml (17.22 mmol) of water, and 0.99 g (0.86 mmol) of tetrakis(triphenylphosphine)palladium(0) in 80 ml of dioxane was heated to 90° C. under a nitrogen atm. overnight. The reaction was cooled to room temperature, diluted with ethyl acetate and washed with saturated sodium bicarbonate. The organic phase was dried over magnesium sulfate. Filtration, removal of solvent and purification of the residue via biotage eluting with 60% ethyl acetate/hexanes gave 0.37 g (82.55%) of product.

Workup

customovernight
temperatureThe reaction was cooled to room temperature
washwashed with saturated sodium bicarbonate
dry with materialThe organic phase was dried over magnesium sulfate
filtrationFiltration, removal of solvent and purification of the residue via biotage
washeluting with 60% ethyl acetate/hexanes

Sources & evidence

ORD record: ord-c0f5b9f8ada249768f823bb17f655fee
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07897607B2

Reaction notes

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