Water → N-methanesulfonyl-6-cyanomethylindole

HRID 618270ノート

反応式

HRID 618270 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

HCID 18789651N-methanesulfonyl-6-cyanomethylindole収率 95.1%

試薬・触媒・溶媒 2

HCID 8857Ethyl Acetate溶媒HCID 312751,4-Dioxane溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-2ae54134c4b447338d3a78138de5e92a
出典データセット
uspto-grants-1999_09
特許番号
US05952362

反応ノート

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