Potassium Carbonate → HCID 66790902, compound

HRID 1929435Notes

Reaction equation

HRID 1929435 reaction equation
Cl[C:2]1[C:3]([N+:22]([O-:24])=[O:23])=[CH:4][C:5]2[O:10][C:9]([CH3:12])([CH3:11])[C:8](=[O:13])[N:7]([C:14]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=3)[C:6]=2[CH:21]=1.[C:25](=O)([O-])[O-].[K+].[K+].CB1OB(C)OB(C)O1>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.O1CCOCC1>[F:20][C:17]1[CH:18]=[CH:19][C:14]([N:7]2[C:6]3[CH:21]=[C:2]([CH3:25])[C:3]([N+:22]([O-:24])=[O:23])=[CH:4][C:5]=3[O:10][C:9]([CH3:12])([CH3:11])[C:8]2=[O:13])=[CH:15][CH:16]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 574072TrimethylboroxineHCID 66790552HCID 66790552, compound

Product 1

HCID 66790902HCID 66790902, compoundYield 5.3%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

To a mixture of 6-chloro-4-(4-fluorophenyl)-2,2-dimethyl-7-nitro-2H-1,4-benzoxazin-3(4H)-one (compound obtained in Reference Example 50(2); 200 mg), potassium carbonate (236 mg), tetrakis(triphenylphosphine)palladium(0) (66 mg) and dioxane (2 mL) was added trimethylboroxin (80 μL) under argon atmosphere, and the mixture was refluxed under heating for 18 hours. After cooling, the reaction mixture was filtered through a celite pad, and the insolubles were washed with tetrahydrofuran. The filtrate and the washings were combined and concentrated in vacuo. The resultant residue was purified by column chromatography on silica gel (solvent; n-hexane/ethyl acetate=9/1) to give 4-(4-fluorophenyl)-2,2,6-trimethyl-7-nitro-2H-1,4-benzoxazin-3(4H)-one (10 mg) as a pale yellow powder.

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureunder heating for 18 hours
  3. temperatureAfter cooling
  4. filtrationthe reaction mixture was filtered through a celite pad
  5. washthe insolubles were washed with tetrahydrofuran
  6. concentrationconcentrated in vacuo
  7. customThe resultant residue was purified by column chromatography on silica gel (solvent; n-hexane/ethyl acetate=9/1)

Sources & evidence

ORD record
ord-215d0cfa0a2e42ad86a0b3c1f1c4d6e0
Source dataset
uspto-grants-2012_05
Patent number
US08188073B2

Reaction notes

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