Dimethylformamide → 8-Methoxycarbonyl-7-(2-methoxyphenyl)-3,3-dimethyl-3,4-dihydro-1H-quinoxalin-2-one

HRID 1038467Notes

Reaction equation

HRID 1038467 reaction equation
Br[C:2]1[C:11]([C:12]([O:14][CH3:15])=[O:13])=[C:10]2[C:5]([NH:6][C:7]([CH3:18])([CH3:17])[C:8](=[O:16])[NH:9]2)=[CH:4][CH:3]=1.[CH3:19][O:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1B(O)O.C(=O)([O-])[O-].CN(C)C=O>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O.C(OCC)(=O)C>[CH3:15][O:14][C:12]([C:11]1[C:2]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=2[O:20][CH3:19])=[CH:3][CH:4]=[C:5]2[C:10]=1[NH:9][C:8](=[O:16])[C:7]([CH3:18])([CH3:17])[NH:6]2)=[O:13]

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 19660Carbonate IonHCID 27339582-Methoxyphenylboronic acidHCID 24780709Methyl 6-bromo-2,2-dimethyl-3-oxo-1,2,3,4-tetrahydroquinoxaline-5-carboxylate

Product 1

HCID 247808448-Methoxycarbonyl-7-(2-methoxyphenyl)-3,3-dimethyl-3,4-dihydro-1H-quinoxalin-2-oneYield 53.3%

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 7-bromo-8-methoxycarbonyl-3,3-dimethyl-3,4-dihydro-1H-quinoxalin-2-one (Reference Compound No. 1, 203 mg, 0.64 mmol), 2-methoxyphenylboronic acid (196 mg, 1.28 mmol), cessium carbonate (629 mg, 1.92 mmol) and bis(triphenylphosphine)palladium dichloride (II) (45.8 mg, 0.06 mmol) was suspended with anhydrous N,N-dimethylformamide (3 ml) and stirred at 80° C. for 2 days. After the mixture was cooled down, ethyl acetate (30 mL) and water (30 mL) were added thereto and the mixture was partitioned. The organic layer was washed with water (30 mL) and saturated brine (30 mL) successively, dried over anhydrous magnesium sulfate, and then the solvent was removed under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate) to give the titled reference compound (116 mg) as a pale yellow amorphous product. (Yield 31%)

Workup

  1. temperatureAfter the mixture was cooled down
  2. customthe mixture was partitioned
  3. washThe organic layer was washed with water (30 mL) and saturated brine (30 mL) successively
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was removed under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-641a2de55a3049cf9da8634a9b4d6113
Source dataset
uspto-grants-2013_10
Patent number
US08551991B2

Reaction notes

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