Isatin → 1-(Prop-2-yn-1-yl)-1H-indole-2,3-dione

HRID 252618

反応式

HRID 252618 の反応式
[NH:1]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4](=[O:5])[C:2]1=[O:3].C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:18](Br)[C:19]#[CH:20]>CN(C=O)C>[CH2:20]([N:1]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4](=[O:5])[C:2]1=[O:3])[C:19]#[CH:18]

参加物

5

反応物 3

HCID 7054IsatinHCID 7842Propargyl bromideHCID 10796Cesium carbonate

生成物 1

HCID 19090021-(Prop-2-yn-1-yl)-1H-indole-2,3-dione

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of isatin (200 mg, 1.36 mmol) in DMF (5 mL) was added cesium carbonate (487 mg, 1.5 mmol). The reaction was stirred at room temperature for 90 minutes. Propargyl bromide (243 uL, 1.63 mmol) was then added. The reaction was stirred overnight at room temperature, concentrated in vacuo, dissolved in EtOAc and washed with saturated NaHCO3(aq) (1×). The layers were separated and the aqueous layer was extracted with additional EtOAc (2×). The combined organic phases was dried over Na2SO4, filtered and concentrated in vacuo. Further purification of the residue was not necessary. The title compound was obtained as an orange solid (255 mg, quantitative yield). 1H NMR (400 MHz, CDCl3) δ 2.31 (t, J=2.54 Hz, 1H), 4.55 (d, J=2.54 Hz, 2H), 7.12-7.15 (m, 1H), 7.19 (dt, J=7.52, 0.78 Hz, 1H), 7.63-7.68 (m, 2H).

後処理

  1. stirringThe reaction was stirred overnight at room temperature
  2. concentrationconcentrated in vacuo
  3. dissolutiondissolved in EtOAc
  4. washwashed with saturated NaHCO3(aq) (1×)
  5. customThe layers were separated
  6. extractionthe aqueous layer was extracted with additional EtOAc (2×)
  7. dry with materialThe combined organic phases was dried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customFurther purification of the residue

出典と根拠

ORDレコード
ord-cba8be419ff846ea9f6491f2ebc15bac
出典データセット
uspto-grants-2011_01
特許番号
US07868181B2

関連ノート

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