Benzenesulfinic acid, sodium salt → HCID 178452229, 화합물

HRID 1292994

반응식

HRID 1292994 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:24]1([S:30]([O-:32])=[O:31])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.[Na+]>[Cu]I.CN(C)C=O>[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:30]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)(=[O:32])=[O:31])=[N:17][NH:18]3)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

참가 물질

5

반응물 2

HCID 2723840Benzenesulfinic acid, sodium saltHCID 178452228HCID 178452228, 화합물

생성물 1

HCID 178452229HCID 178452229, 화합물수율 18%

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 6228Dimethylformamide용매

반응 조건

온도
125 °C

실험 절차

A mixture of 4-[4-(t-butoxycarbonyl)piperazin-1-yl]-3-iodo-1H-indazole (0.110 g, 0.257 mmol), sodium benzene sulfinate (0.068 g, 0.411 mmol), copper(I) iodide (0.073 g, 0.386 mmol) and N,N-dimethylformamide is added to a screw-capped test-tube with Teflon-lined septum. The tube is evacuated and backfilled with argon. This procedure is repeated twice, then the tube is heated to 125° C. for 4 h. The reaction mixture is cooled, partitioned between ethyl acetate and water and filtered through a pad of diatomaceous earth. The filtrate is separated. The organic phase is washed with brine, dried over sodium sulfate and concentrated in vacuo. The resulting crude material is purified by column chromatography (silica gel, 40:60 ethyl acetate/hexanes) to afford the title compound as a pale yellow foam, 0.022 g (18% yield), identified by NMR and mass spectral analyses.

후처리

  1. customThe tube is evacuated
  2. temperatureThe reaction mixture is cooled
  3. custompartitioned between ethyl acetate and water
  4. filtrationfiltered through a pad of diatomaceous earth
  5. customThe filtrate is separated
  6. washThe organic phase is washed with brine
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated in vacuo
  9. customThe resulting crude material is purified by column chromatography (silica gel, 40:60 ethyl acetate/hexanes)

출처 및 근거

ORD 기록
ord-fd3f2ecc43624aef9247ea38a5a4a617
출처 데이터셋
uspto-grants-2007_07
특허 번호
US07238696B2

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