Toluene → 1-Methyl-6-(1-phenylsulfanyl-cyclopropoxy)-3,4-dihydro-1H-quinolin-2-one

HRID 1244018노트

반응식

HRID 1244018 반응식
C1(C)C=CC=CC=1.I[C:9]1([S:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:11][CH2:10]1.[OH:19][C:20]1[CH:21]=[C:22]2[C:27](=[CH:28][CH:29]=1)[N:26]([CH3:30])[C:25](=[O:31])[CH2:24][CH2:23]2>C(=O)([O-])[O-].[Ag+2].C(OCC)(=O)C.CCCCCC>[CH3:30][N:26]1[C:27]2[C:22](=[CH:21][C:20]([O:19][C:9]3([S:12][C:13]4[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=4)[CH2:11][CH2:10]3)=[CH:29][CH:28]=2)[CH2:23][CH2:24][C:25]1=[O:31]

참가 물질

6

반응물 3

HCID 1140TolueneHCID 11000298(1-Iodocyclopropyl)(phenyl)sulfaneHCID 219318286-Hydroxy-1-methyl-3,4-dihydroquinolin-2(1H)-one

생성물 1

HCID 219318121-Methyl-6-(1-phenylsulfanyl-cyclopropoxy)-3,4-dihydro-1H-quinolin-2-one수율 17.4%

시약·촉매·용매 2

HCID 178418647HCID 178418647, 화합물촉매HCID 21226206Ethyl acetate hexane용매

반응 조건

온도
55 °C

실험 절차

To a dry toluene solution of [1-Iodo-cyclopropylsulfanyl]-benzene (375 mg, 1.36 mmol) was added 6-Hydroxy-1-methyl-3,4-dihydro-1H-quinolin-2-one (200 mg, 1.13 mmol) and silver carbonate (312 mg, 1.13 mmol) under nitrogen and the reaction mixture was heated to 55° C. It took 3 more additions of the reagents to take the reaction to completion. The reaction was cooled to room temperature, filtered to remove the silver iodide and concentrated under vacuum to yield crude material. This was flash chromatograhed using 30% ethyl acetate/hexane to yield the title compound as a viscous oil (64 mg, 17% yield). 1H NMR (400 MHz, CDCl3) δ 1.31–1.33 (2H, m), 1.41–1.43 (2H, m), 2.59–2.62 (2H, m), 2.83–2.87 (2H, m), 3.31 (3H, s), 6.86–6.98 (4H, m), 7.20–7.31 (2H, m), 7.44–7.47 (2H, m). m/z (APCI+) 326 (M+1). HPLC (aqueous 200 Mm ammonium acetate buffer/acetonitrile gradient, 3.0 ml/min, Hewlett Packard ODS Hypersil 5 μM, 125×4 mm column), 6.59 minutes.

후처리

  1. customthe reaction to completion
  2. temperatureThe reaction was cooled to room temperature
  3. filtrationfiltered
  4. customto remove the silver iodide
  5. concentrationconcentrated under vacuum
  6. customto yield crude material

출처 및 근거

ORD 기록
ord-bf963116c7e54b6e8086ec5913dc2775
출처 데이터셋
uspto-grants-2006_10
특허 번호
US07119207B2

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