Potassium tert-butoxide → 5-nitro-2-(pyridin-2-yl)-1H-indole

HRID 468378

반응식

HRID 468378 반응식
[N+:1]([C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[C:6]([C:11]#[C:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)[CH:5]=1)([O-:3])=[O:2].CC([O-])(C)C.[K+]>CN(C=O)C.O>[N+:1]([C:4]1[CH:5]=[C:6]2[C:7](=[CH:9][CH:10]=1)[NH:8][C:12]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=1)=[CH:11]2)([O-:3])=[O:2]

참가 물질

5

반응물 2

HCID 23665647Potassium tert-butoxideHCID 591291894-Nitro-2-(pyridin-2-ylethynyl)aniline

생성물 1

HCID 591293805-nitro-2-(pyridin-2-yl)-1H-indole수율 67%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

반응 조건

온도
90 °C

실험 절차

To the solution of 4-nitro-2-(pyridin-2-ylethynyl)aniline (1.5 g, 6.3 mmol) in DMF (50 mL) was added t-BuOK (1.5 g, 13 mmol). The reaction mixture was stirred at 90° C. for 2 h. The mixture was diluted with water and extracted with dichloromethane (3×50 mL). The combined organic layers were washed with brine, dried over anhydrous Na2SO4 and concentrated in vacuum. The residue was purified by chromatography on silica gel (5-10% ethyl acetate/petroleum ether) to afford 5-nitro-2-(pyridin-2-yl)-1H-indole (1.0 g, 67% yield). 1H NMR (300 MHz, d-DMSO) δ 12.40 (s, 1H), 8.66 (d, J=2.1 Hz, 1H), 8.58 (d, J=1.8 Hz, 1H), 8.07-7.91 (m, 3H), 7.59 (d, J=6.6 Hz, 1H), 7.42-7.37 (m, 2H).

후처리

  1. extractionextracted with dichloromethane (3×50 mL)
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated in vacuum
  5. customThe residue was purified by chromatography on silica gel (5-10% ethyl acetate/petroleum ether)

출처 및 근거

ORD 기록
ord-3528aebc83f1476abb83b6ce27a59101
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08623905B2

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