Iodoethane → 1-Ethyl-2-methyl-6-nitro-1H-indole

HRID 2079914

반응식

HRID 2079914 반응식
[CH3:1][C:2]1[NH:3][C:4]2[C:9]([CH:10]=1)=[CH:8][CH:7]=[C:6]([N+:11]([O-:13])=[O:12])[CH:5]=2.C[Si](C)(C)[N-][Si](C)(C)C.[Na+].I[CH2:25][CH3:26].C(OCC)(=O)C>CN(C=O)C>[CH2:25]([N:3]1[C:4]2[C:9](=[CH:8][CH:7]=[C:6]([N+:11]([O-:13])=[O:12])[CH:5]=2)[CH:10]=[C:2]1[CH3:1])[CH3:26]

참가 물질

6

반응물 4

HCID 6340IodoethaneHCID 8857Ethyl AcetateHCID 6005082-Methyl-6-nitro-1H-indoleHCID 2724254Sodium bis(trimethylsilyl)amide

생성물 1

HCID 574422751-Ethyl-2-methyl-6-nitro-1H-indole수율 100%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

Cool a solution of 2-methyl-6-nitro-1H-indole, 18 (0.31 g, 1.76 mmol) in anhydrous DMF (5 mL) under inert atmosphere at 0° C. Add sodium hexamethyldisilazide (1.0M in THF, 1.9 mL, 1.9 mmol) and stir 5 minutes. Add iodoethane (filtered through basic alumina) (0.43 mL, 5.28 mmol), warm to ambient temperature, and stir 2 hours. Quench the reaction with saturated aqueous sodium bicarbonate, add ethyl acetate, and wash with saturated aqueous sodium bicarbonate followed by saturated aqueous brine. Dry the organic layer over sodium sulfate, filter, and concentrate in vacuo. Chromatograph over silica gel using hexanes/ethyl acetate (9:1) to afford the title compound, (0.36 g, 100%). 1H NMR (CDCl3, 300 MHz) δ 2.47 (s, 31), 4.18 (q, J=7.1 Hz, 2), 6.23 (s, 3H), 7.48 (d, J=8.8 Hz, 1H), 7.95 (dd, J=1.9, 8.6 Hz, 1H), 8.23 (d, J=1.9 Hz, 1H).

후처리

  1. customQuench
  2. customthe reaction with saturated aqueous sodium bicarbonate
  3. washwash with saturated aqueous sodium bicarbonate
  4. dry with materialDry the organic layer over sodium sulfate
  5. filtrationfilter
  6. concentrationconcentrate in vacuo

출처 및 근거

ORD 기록
ord-8c02373d2b1848c2b67e6759d8ead9b2
출처 데이터셋
uspto-grants-2011_04
특허 번호
US07932284B2

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