Water → N-methanesulfonyl-6-cyanomethylindole

HRID 618270노트

반응식

HRID 618270 반응식
[CH3:1][S:2]([N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([CH2:14]Br)[CH:12]=2)[CH:7]=[CH:6]1)(=[O:4])=[O:3].O.[C-:17]#[N:18].[Na+]>O1CCOCC1.C(OCC)(=O)C>[CH3:1][S:2]([N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([CH2:14][C:17]#[N:18])[CH:12]=2)[CH:7]=[CH:6]1)(=[O:4])=[O:3]

참가 물질

6

반응물 3

HCID 962WaterHCID 8929Sodium CyanideHCID 18789641N-methanesulfonyl-6-bromomethylindole

생성물 1

HCID 18789651N-methanesulfonyl-6-cyanomethylindole수율 95.1%

시약·촉매·용매 2

HCID 8857Ethyl Acetate용매HCID 312751,4-Dioxane용매

실험 절차

N-methanesulfonyl-6-bromomethylindole (280 mg, 0.97 mmol, from above) was dissolved in 1 ml of dioxane. Water (1 mL) was added followed by NaCN (52 mg, 1.07 mmol). The mixture was stirred for 9 days at room temperature. The reaction mixture was diluted with 30 ml of ethyl acetate and washed with 10 ml water. The aqueous layer was washed with 30 ml ethyl acetate. The combined extracts were washed with brine, dried (Na2SO4), and concentrated. The crude product was purified by flash column chromatography (silica gel, 40% ethyl acetate/hexane) to give 216 mg of the desired N-methanesulfonyl-6-cyanomethylindole (95% yield).

후처리

  1. washwashed with 10 ml water
  2. washThe aqueous layer was washed with 30 ml ethyl acetate
  3. washThe combined extracts were washed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customThe crude product was purified by flash column chromatography (silica gel, 40% ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-2ae54134c4b447338d3a78138de5e92a
출처 데이터셋
uspto-grants-1999_09
특허 번호
US05952362

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