Sodium Carbonate → 8-(2,4-Dimethylphenyl)-2-methyl-2H-1,4-benzoxazin-3(4H)-one

HRID 598066Notes

Reaction equation

HRID 598066 reaction equation
Br[C:2]1[C:11]2[O:10][CH:9]([CH3:12])[C:8](=[O:13])[NH:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.[CH3:14][C:15]1[CH:20]=[C:19]([CH3:21])[CH:18]=[CH:17][C:16]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.O.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>[CH3:14][C:15]1[CH:20]=[C:19]([CH3:21])[CH:18]=[CH:17][C:16]=1[C:2]1[C:11]2[O:10][CH:9]([CH3:12])[C:8](=[O:13])[NH:7][C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 4198739(2,4-Dimethylphenyl)boronic acidHCID 672673248-Bromo-2-methyl-3,4-dihydro-2H-1,4-benzoxazin-3-one

Product 1

HCID 589385588-(2,4-Dimethylphenyl)-2-methyl-2H-1,4-benzoxazin-3(4H)-oneYield 91%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

To a solution of 8-bromo-2-methyl-2H-1,4-benzoxazin-3(4H)-one (1.20 g, 4.96 mmol) in 1,2-dimethoxyethane (50 ml) were added 2,4-dimethylphenylboronic acid (818 mg, 5.45 mmol), tetrakis(triphenylphosphine)palladium(0) (286 mg, 0.245 mmol) and 2M sodium carbonate solution (4.96 ml, 9.92 mmol). The mixture was refluxed for 16 h and diluted with water. The aqueous solution was extracted with ethyl acetate. The extract was washed with brine, dried over magnesium sulfate and concentrated under vacuum. The residue was purified by column chromatography eluting with 20% ethyl acetate/n-hexane to afford 1.20 g (91%) of the title compound.

Workup

  1. temperatureThe mixture was refluxed for 16 h
  2. extractionThe aqueous solution was extracted with ethyl acetate
  3. washThe extract was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under vacuum
  6. customThe residue was purified by column chromatography
  7. washeluting with 20% ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-94d21bd4795542649de8a5558e28f6f4
Source dataset
uspto-grants-2011_03
Patent number
US07897607B2

Reaction notes

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