Potassium Carbonate → HCID 67340992, compound

HRID 1929438Notes

Reaction equation

HRID 1929438 reaction equation
[NH2:1][C:2]1[CH:21]=[C:20](Br)[C:5]2[N:6]([C:13]3[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=3)[C:7](=[O:12])[C:8]([CH3:11])([CH3:10])[O:9][C:4]=2[CH:3]=1.[C:23](=O)([O-])[O-].[K+].[K+].O1CCOCC1.CB1OB(C)OB(C)O1>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].O>[NH2:1][C:2]1[CH:21]=[C:20]([CH3:23])[C:5]2[N:6]([C:13]3[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=3)[C:7](=[O:12])[C:8]([CH3:11])([CH3:10])[O:9][C:4]=2[CH:3]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 574072TrimethylboroxineHCID 66789962HCID 66789962, compound

Product 1

HCID 67340992HCID 67340992, compoundYield 88.6%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolvent

Procedure

A mixture of 7-amino-5-bromo-4-(4-fluorophenyl)-2,2-dimethyl-2H-1,4-benzoxazin-3(4H)-one (compound obtained in Reference Example 53(7); 140 mg), potassium carbonate (159 mg), dioxane (11 mL), trimethylboroxin (134 μL) and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (31 mg) was refluxed under argon atmosphere for 2 hours. After cooling, to the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate and concentrated in vacuo. The resultant residue was purified by column chromatography on silica gel (solvent; n-hexane/ethyl acetate=3/1→3/7) to give 7-amino-4-(4-fluorophenyl)-2,2,5-trimethyl-2H-1,4-benzoxazin-3(4H)-one (102 mg) as a pale yellow powder.

Workup

  1. temperaturewas refluxed under argon atmosphere for 2 hours
  2. temperatureAfter cooling, to the reaction mixture
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe resultant residue was purified by column chromatography on silica gel (solvent; n-hexane/ethyl acetate=3/1→3/7)

Sources & evidence

ORD record
ord-fc8feeadd12d4241a47920a61724a86e
Source dataset
uspto-grants-2012_05
Patent number
US08188073B2

Reaction notes

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