Potassium Iodide → 5-(1H-Indol-3-yl)pentanoic acid cyanomethyl ester

HRID 908939노트

반응식

HRID 908939 반응식
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][CH2:11][CH2:12][CH2:13][C:14]([OH:16])=[O:15])=[CH:2]1.C(=O)([O-])[O-].[Cs+].[Cs+].Cl[CH2:24][C:25]#[N:26].[I-].[K+]>CC(C)=O.CN(C)C=O>[C:25]([CH2:24][O:15][C:14](=[O:16])[CH2:13][CH2:12][CH2:11][CH2:10][C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[NH:1][CH:2]=1)#[N:26]

참가 물질

7

반응물 4

HCID 4875Potassium IodideHCID 7856ChloroacetonitrileHCID 10796Cesium carbonateHCID 123571275-(1H-indol-3-yl)pentanoic acid

생성물 1

HCID 673867685-(1H-Indol-3-yl)pentanoic acid cyanomethyl ester수율 77%

시약·촉매·용매 2

HCID 180Acetone용매HCID 6228Dimethylformamide용매

실험 절차

5-(1H-Indol-3-yl)pentanoic acid (5 g, 23 mmol) was dissolved in a mixture of acetone (25 ml) and dimethylformamide (25 ml), and caesium carbonate (3.75 g, 11.5 mmol), chloroacetonitrile (2.16 ml, 34.5 mmol) and potassium iodide (20 mg) were added in succession. After 6.5 h at 60° C. and 16 h at RT, the solid residues were filtered off and washed with acetone (2×30 ml) and the filtrate was concentrated. The crude product was purified by chromatography on silica gel (130 g) with EA/cyclohexane (1:3). The product was obtained as a colourless solid with an m.p. of 76° C. in a yield of 77% (4.53 g).

후처리

  1. additionwere added in succession
  2. filtration16 h at RT, the solid residues were filtered off
  3. washwashed with acetone (2×30 ml)
  4. concentrationthe filtrate was concentrated
  5. customThe crude product was purified by chromatography on silica gel (130 g) with EA/cyclohexane (1:3)
  6. customThe product was obtained as a colourless solid with an m.p. of 76° C. in a yield of 77% (4.53 g)

출처 및 근거

ORD 기록
ord-a61b9df88b1f4fec8b934976358ea9f2
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08017630B2

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