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

HRID 1096990노트

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HRID 1096990 반응식
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]

참가 물질

8

반응물 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

생성물 1

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

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 962Water용매HCID 8028Tetrahydrofuran용매

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온도
85 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-672fc8df3947403fbaba208f48e93a03
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08138197B2

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