Water → 2-tert-butyl-5-nitro-1H-indole-4-carbonitrile

HRID 468503노트

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HRID 468503 반응식
[C:1]([C:5]1[NH:6][C:7]2[C:12]([CH:13]=1)=[C:11](F)[C:10]([N+:15]([O-:17])=[O:16])=[CH:9][CH:8]=2)([CH3:4])([CH3:3])[CH3:2].[C-:18]#[N:19].[K+].O>CS(C)=O>[C:1]([C:5]1[NH:6][C:7]2[CH:8]=[CH:9][C:10]([N+:15]([O-:17])=[O:16])=[C:11]([C:18]#[N:19])[C:12]=2[CH:13]=1)([CH3:4])([CH3:3])[CH3:2]

참가 물질

5

반응물 3

HCID 962WaterHCID 9032Potassium CyanideHCID 534211832-Tert-butyl-4-fluoro-5-nitro-1H-indole

생성물 1

HCID 591295222-tert-butyl-5-nitro-1H-indole-4-carbonitrile수율 53.2%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

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온도
70 °C

실험 절차

To a solution of 2-tert-butyl-4-fluoro-5-nitro-1H-indole (4.0 g, 17 mmol) in DMSO (30 mL) was added KCN (3.4 g, 51 mmol). The mixture was stirred at 70° C. for 3 hours, and poured into water (80 mL) and extracted with ethyl acetate (50 mL×3). The combined organic layers were washed with brine, dried over anhydrous Na2SO4 and concentrated under vacuum. The residue was purified by column chromatography on silica gel (7% EtOAc in petroleum ether) to afford 2-tert-butyl-5-nitro-1H-indole-4-carbonitrile (2.2 g, 53%). 1H NMR (DMSO, 300 MHz) δ 12.23 (br s, 1H), 8.09 (d, J=9.0 Hz, 1H), 7.75 (d, J=9.0 Hz, 1H), 6.50 (s, 1H), 1.38 (s, 9H). MS (ESI) m/z: 244.2 [M-41].

후처리

  1. extractionextracted with ethyl acetate (50 mL×3)
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated under vacuum
  5. customThe residue was purified by column chromatography on silica gel (7% EtOAc in petroleum ether)

출처 및 근거

ORD 기록
ord-b738f50fcb7144538cd76d228d5d9bf7
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08623905B2

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