Potassium Phosphate, Tribasic → Methyl 3,5-diethoxy-4-(isoxazol-4-yl)benzoate

HRID 1096990Notes

Reaction equation

HRID 1096990 reaction equation
Br[C:2]1[C:11]([O:12][CH2:13][CH3:14])=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[O:15][CH2:16][CH3:17].CC1(C)C(C)(C)OB([C:26]2[CH:27]=[N:28][O:29][CH:30]=2)O1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1>C1COCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[CH2:16]([O:15][C:3]1[CH:4]=[C:5]([CH:10]=[C:11]([O:12][CH2:13][CH3:14])[C:2]=1[C:26]1[CH:27]=[N:28][O:29][CH:30]=1)[C:6]([O:8][CH3:9])=[O:7])[CH3:17]

Participants

8

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 164141804-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2-oxazoleHCID 57930905Methyl 4-bromo-3,5-diethoxybenzoate

Product 1

HCID 57931014Methyl 3,5-diethoxy-4-(isoxazol-4-yl)benzoate

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
85 °C

Procedure

Methyl 4-bromo-3,5-diethoxybenzoate (456 mg) and 4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-isoxazole (438 mg) were dissolved in THF in a nitrogen atmosphere, and potassium phosphate (954 mg), palladium acetate (33 mg) and dicyclohexyl-(2′,6′-dimethoxy-biphenyl-2-yl)-phosphane (62 mg) were added to it, and degassed. The reaction liquid was stirred overnight at 85° C., then cooled to room temperature, water was added to it, and filtered through Celite. The filtrate was extracted with chloroform, washed with saturated saline water, and the organic layer was dried with sodium sulfate. Sodium sulfate was removed through filtration, the filtrate was concentrated under reduced pressure, and the residue was purified through silica gel column chromatography (hexanelethyl acetate=100/0 to 80/20) to obtain the title compound as a pale yellow solid.

Workup

  1. additionwere added to it
  2. customdegassed
  3. customThe reaction liquid
  4. temperaturecooled to room temperature
  5. filtrationfiltered through Celite
  6. extractionThe filtrate was extracted with chloroform
  7. washwashed with saturated saline water
  8. dry with materialthe organic layer was dried with sodium sulfate
  9. customSodium sulfate was removed through filtration
  10. concentrationthe filtrate was concentrated under reduced pressure
  11. customthe residue was purified through silica gel column chromatography (hexanelethyl acetate=100/0 to 80/20)

Sources & evidence

ORD record
ord-672fc8df3947403fbaba208f48e93a03
Source dataset
uspto-grants-2012_03
Patent number
US08138197B2

Reaction notes

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