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

HRID 1978025

反応式

HRID 1978025 の反応式
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]

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 11979704Tetrakis(triphenylphosphine)palladium触媒HCID 80711,2-Dimethoxyethane溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
90 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-89b45d9ae1264a8bb277584400006a80
出典データセット
uspto-grants-2001_05
特許番号
US06235786B1

関連ノート

読み込み中…