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

HRID 968285노트

반응식

HRID 968285 반응식
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

참가 물질

6

반응물 2

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

생성물 1

HCID 222885519-chloro-5-ethyl-5H-phenanthridin-6-one수율 63%

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 178418647HCID 178418647, 화합물촉매HCID 6342Acetonitrile용매

반응 조건

온도
23 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-03d06a9bc6054e8f8fda475171888702
출처 데이터셋
uspto-grants-2005_10
특허 번호
US06958347B2

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