Sodium Carbonate → 1-((4'-Butoxy(1,1'-biphenyl)-4-yl)thio)-3-(4,4-dimethyl-2,5-dioxoimidazolidin-1-yl)-2-propanone

HRID 1978025노트

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HRID 1978025 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:9][C:10](=[O:21])[CH2:11][N:12]2[C:16](=[O:17])[C:15]([CH3:19])([CH3:18])[NH:14][C:13]2=[O:20])=[CH:4][CH:3]=1.[CH2:22]([O:26][C:27]1[CH:32]=[CH:31][C:30](B(O)O)=[CH:29][CH:28]=1)[CH2:23][CH2:24][CH3:25].C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.C(OCC)(=O)C.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH2:22]([O:26][C:27]1[CH:32]=[CH:31][C:30]([C:2]2[CH:7]=[CH:6][C:5]([S:8][CH2:9][C:10](=[O:21])[CH2:11][N:12]3[C:16](=[O:17])[C:15]([CH3:19])([CH3:18])[NH:14][C:13]3=[O:20])=[CH:4][CH:3]=2)=[CH:29][CH:28]=1)[CH2:23][CH2:24][CH3:25]

참가 물질

7

반응물 3

HCID 10340Sodium CarbonateHCID 38363104-Butoxyphenylboronic AcidHCID 217002621-(4-Bromophenylthio)-3-(4,4-dimethyl-2,5-dioxoimidazolidin-1-yl)-2-propanone

생성물 1

HCID 110375531-((4'-Butoxy(1,1'-biphenyl)-4-yl)thio)-3-(4,4-dimethyl-2,5-dioxoimidazolidin-1-yl)-2-propanone수율 78.1%

시약·촉매·용매 3

HCID 11979704Tetrakis(triphenylphosphine)palladium촉매HCID 80711,2-Dimethoxyethane용매HCID 8857Ethyl Acetate용매

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온도
90 °C

실험 절차

A solution of Example 46A (700 mg, 1.89 mmol) in DME (20 mL) at room temperature was treated with 4-n-butoxybenzeneboronic acid (549 mg, 2.83 mmol), tetrakis-(triphenylphosphine)-palladium (218 mg, 0.189 mmol) and 1M sodium carbonate (3.54 mL, 3.54 mmol), the reaction vessel was sealed and heated at 90° C. for 6 hours, diluted with ethyl acetate, washed with sequentially saturated ammonium chloride solution, water and brine, dried (Na2SO4), filtered, concentrated and purified on silica gel with 30 to 50% ethyl acetate/dichloromethane to provide 650 mg (78%) of the desired product as a yellow solid.

후처리

  1. customthe reaction vessel was sealed
  2. washwashed with sequentially saturated ammonium chloride solution, water and brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified on silica gel with 30 to 50% ethyl acetate/dichloromethane

출처 및 근거

ORD 기록
ord-89b45d9ae1264a8bb277584400006a80
출처 데이터셋
uspto-grants-2001_05
특허 번호
US06235786B1

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