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

HRID 1244018ノート

反応式

HRID 1244018 の反応式
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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 178418647HCID 178418647、化合物触媒HCID 21226206Ethyl acetate hexane溶媒

反応条件

温度
55 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-bf963116c7e54b6e8086ec5913dc2775
出典データセット
uspto-grants-2006_10
特許番号
US07119207B2

反応ノート

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