Sodium Carbonate → N-(3-benzoyl-5-phenyl-thiophen-2-yl)-acetamide

HRID 133546

反応式

HRID 133546 の反応式
[C:1]([C:9]1[CH:13]=[C:12](Br)[S:11][C:10]=1[NH:15][C:16](=[O:18])[CH3:17])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:19]1(B(O)O)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.CCO.[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>[C:1]([C:9]1[CH:13]=[C:12]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[S:11][C:10]=1[NH:15][C:16](=[O:18])[CH3:17])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

7

反応物 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 16640231N-(3-benzoyl-5-bromo-thiophen-2-yl) acetamide

生成物 1

HCID 68895390N-(3-benzoyl-5-phenyl-thiophen-2-yl)-acetamide収率 88.6%

試薬・触媒・溶媒 3

HCID 11979704Tetrakis(triphenylphosphine)palladium触媒HCID 702Ethanol溶媒HCID 1140Toluene溶媒

反応条件

温度
90 °C

実験手順

A stirred solution of 0.448 g (1.38 mmol) of N-(3-benzoyl-5-bromo-thiophen-2-yl) acetamide in 20 ml toluene and 10 ml EtOH was degassed with argon. Tetrakis-(triphenylphosphine) palladium (0) (0.320 g, 0.27 mmol), phenyl boronic acid (0.194 g, 1.59 mmol) and 20 ml of an aqueous solution of Na2CO3 1N were added. The mixture was heated at 90° C. for 1 hour before cooling down to RT, filtered through Celite and concentrated. The mixture was extracted with ethyl acetate and aq. NaHCO3. The combined organic phases were dried over sodium sulfate and concentrated in vacuo. Flash chromatography (heptane/ethyl acetate 6:1) afforded 0.393 g (88%) N-(3-benzoyl-5-phenyl-thiophen-2-yl)-acetamide as a light yellow solid. ES-MS m/e (%): 322 (M+H+, 100).

後処理

  1. temperaturebefore cooling down to RT
  2. filtrationfiltered through Celite
  3. concentrationconcentrated
  4. extractionThe mixture was extracted with ethyl acetate and aq. NaHCO3
  5. dry with materialThe combined organic phases were dried over sodium sulfate
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-05943aea103c471bbd9ee1e2aee9c135
出典データセット
uspto-grants-2008_06
特許番号
US07390903B2

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