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

HRID 227308

반응식

HRID 227308 반응식
[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]

참가 물질

8

반응물 4

HCID 174Ethylene GlycolHCID 11430Potassium CarbonateHCID 682591-NaphthalenethiolHCID 178452228HCID 178452228, 화합물

생성물 1

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

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 3776Isopropanol용매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-306fa838894a4c9a85c2abf0057dcb50
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07560470B2

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