Isoamyl Nitrite → 6-Iodoindane-5-carbonitrile

HRID 537976노트

반응식

HRID 537976 반응식
N[C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][CH2:8]2)=[CH:4][C:3]=1[C:11]#[N:12].N(OCCC(C)C)=O.[I-:21]>>[I:21][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][CH2:8]2)=[CH:4][C:3]=1[C:11]#[N:12]

참가 물질

4

반응물 3

HCID 8053Isoamyl NitriteHCID 30165Iodide IonHCID 451221766-amino-2,3-dihydro-1H-indene-5-carbonitrile

생성물 1

HCID 575762696-Iodoindane-5-carbonitrile수율 50%

실험 절차

A mixture of 6-aminoindane-5-carbonitrile (48.5 mg, 0.307 mmol), isoamyl nitrite (82 μL, 0.614 mmol) and iodide (85.7 mg, 0.338 mmol) was stirred at room temperature for 0.5 h. The mixture was then heated at 80° C. under N2 for 2 h. The reaction mixture was quenched with saturated Na2S2O3 and partitioned between dichloromethane and water. The organic layer was dried (Na2SO4) and concentrated in vacuo. The residue was purified by flash chromatography (Si, 1% EtOAc in hexanes) to yield 6-iodoindane-5-carbonitrile (39.7 mg, 50%). LCMS calc.=268.97; found=270.0 (M+1)+. 1H NMR (500 MHz, CDCl3) δ 7.78 (s, 1H), 7.48 (s, 1H), 2.96 (t, J=7.5 Hz, 2H), 2.92 (t, J=7.5 Hz, 2H), 2.16-2.10 (m, 2H).

후처리

  1. temperatureThe mixture was then heated at 80° C. under N2 for 2 h
  2. customThe reaction mixture was quenched with saturated Na2S2O3
  3. custompartitioned between dichloromethane and water
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography (Si, 1% EtOAc in hexanes)

출처 및 근거

ORD 기록
ord-c97ea78117d24a6b891bf66e00699de4
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08865707B2

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