Ethylene Glycol → 4-[4-(t-Butoxycarbonyl)piperazin-1-yl]-3-(1-naphthylthio)-1H-indazole

HRID 227308

反応式

HRID 227308 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:22]=[CH:21][CH:20]=[C:19]3[C:15]=2[C:16](I)=[N:17][NH:18]3)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].C(O)CO.[C:34]1([SH:44])[C:43]2[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=2)[CH:37]=[CH:36][CH:35]=1>C(OCC)(=O)C.[Cu]I.CC(O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:22]=[CH:21][CH:20]=[C:19]3[C:15]=2[C:16]([S:44][C:34]2[C:43]4[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=4)[CH:37]=[CH:36][CH:35]=2)=[N:17][NH:18]3)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

参加物

8

反応物 4

HCID 174Ethylene GlycolHCID 11430Potassium CarbonateHCID 682591-NaphthalenethiolHCID 178452228HCID 178452228、化合物

生成物 1

HCID 589047834-[4-(t-Butoxycarbonyl)piperazin-1-yl]-3-(1-naphthylthio)-1H-indazole収率 45%

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 3776Isopropanol溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A mixture of 4-[4-(t-butoxycarbonyl)piperazin-1-yl]-3-iodo-1H-indazole (0.068 g, 0.159 mmol), copper(I) iodide (0.005 g, 0.024 mmol) and potassium carbonate (0.044 g, 0.318 mmol) are added to a screw-capped test tube with a Teflon-lined septum. The tube is evacuated and backfilled with argon and this procedure repeated twice more. The reaction mixture is treated sequentially with 2-propanol (1.5 mL), ethylene glycol (19 μL, 0.318 mmol) and 1-naphthalenethiol (0.051 g, 0.318 mmol), heated at 130°-140° C. for 8 h, cooled to room temperature, diluted with ethyl acetate and filtered through diatomaceous earth. The filtrate is concentrated under reduced pressure. The resultant crude material is purified by flash chromatography (silica gel, 40:60 ethyl acetate/hexanes) to afford the title compound as a colorless oil, 0.033 g (45% yield), identified by NMR and mass spectral analyses.

後処理

  1. customThe tube is evacuated
  2. temperatureheated at 130°-140° C. for 8 h
  3. filtrationfiltered through diatomaceous earth
  4. concentrationThe filtrate is concentrated under reduced pressure
  5. customThe resultant crude material is purified by flash chromatography (silica gel, 40:60 ethyl acetate/hexanes)

出典と根拠

ORDレコード
ord-306fa838894a4c9a85c2abf0057dcb50
出典データセット
uspto-grants-2009_07
特許番号
US07560470B2

関連ノート

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