Triphenylphosphine → 9-chloro-5-ethyl-5H-phenanthridin-6-one

HRID 968285ノート

反応式

HRID 968285 の反応式
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cl:20][C:21]1[CH:37]=[CH:36][C:24]([C:25]([N:27]([CH2:34][CH3:35])[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[O:26])=[C:23](I)[CH:22]=1>C(#N)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(=O)([O-])[O-].[Ag+2]>[Cl:20][C:21]1[CH:37]=[C:36]2[C:24]([C:25](=[O:26])[N:27]([CH2:34][CH3:35])[C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=32)=[CH:23][CH:22]=1

参加物

6

反応物 2

HCID 11776TriphenylphosphineHCID 222885394-chloro-N-ethyl-2-iodo-N-phenyl-benzamide

生成物 1

HCID 222885519-chloro-5-ethyl-5H-phenanthridin-6-one収率 63%

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 178418647HCID 178418647、化合物触媒HCID 6342Acetonitrile溶媒

反応条件

温度
23 °C

実験手順

Palladium acetate (466 mg, 2.07 mol) was added to a suspension of silver carbonate (5.7 g, 20.7 mmol), triphenylphosphine (1.08 g, 4.15 mmol), and 4-chloro-N-ethyl-2-iodo-N-phenyl-benzamide I-14a (4.0 g, 10.4 mmol) in acetonitrile (52 ml). The reaction mixture was heated to reflux for 1 hour and cooled to 23° C. The mixture was filtered through a plug of celite and the filter cake was washed with ethyl acetate (50 ml) and diethyl ether (50 ml). The combined filtrates were washed with saturated sodium chloride (50 ml), dried over anhydrous sodium sulfate, and then concentrated. The residue was purified by flash column chromatography (1% ethyl acetate in dichloromethane grading to 2% ethyl acetate in dichloromethane) to afford 9-Chloro-5-ethyl-5H-phenanthridin-6-one I-14b (1.68 g, 63%) as a yellow solid.

後処理

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 1 hour
  3. filtrationThe mixture was filtered through a plug of celite
  4. washthe filter cake was washed with ethyl acetate (50 ml) and diethyl ether (50 ml)
  5. washThe combined filtrates were washed with saturated sodium chloride (50 ml)
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated
  8. customThe residue was purified by flash column chromatography (1% ethyl acetate in dichloromethane grading to 2% ethyl acetate in dichloromethane)

出典と根拠

ORDレコード
ord-03d06a9bc6054e8f8fda475171888702
出典データセット
uspto-grants-2005_10
特許番号
US06958347B2

反応ノート

読み込み中…