Water → 2-Tert-butyl-4-fluoro-5-nitro-1H-indole

HRID 468340노트

반응식

HRID 468340 반응식
[C:1]([C:5]1[NH:6][C:7]2[C:12]([CH:13]=1)=[C:11]([F:14])[CH:10]=[CH:9][CH:8]=2)([CH3:4])([CH3:3])[CH3:2].[N+:15]([O-])([O-:17])=[O:16].[K+].O>OS(O)(=O)=O>[C:1]([C:5]1[NH:6][C:7]2[C:12]([CH:13]=1)=[C:11]([F:14])[C:10]([N+:15]([O-:17])=[O:16])=[CH:9][CH:8]=2)([CH3:4])([CH3:2])[CH3:3]

참가 물질

5

반응물 3

HCID 962WaterHCID 24434Potassium NitrateHCID 591292402-tert-butyl-4-fluoro-1H-indole

생성물 1

HCID 534211832-Tert-butyl-4-fluoro-5-nitro-1H-indole수율 73%

시약·촉매·용매 1

HCID 1118Sulfuric Acid용매

반응 조건

온도
-10 °C

실험 절차

To a solution of 2-tert-butyl-4-fluoro-1H-indole (2.5 g, 10 mmol) in H2SO4 (30 mL) was added KNO3 (1.3 g, 10 mmol) at 0° C. The mixture was stirred for 0.5 h at −10° C. The mixture was poured into water and extracted with EtOAc (100 mL×3). The organic layers were washed with sat. NaCl and water, dried over anhydrous Na2SO4, and evaporated under vacuum. The crude compound was purified by column chromatography on silica gel (10% EtOAc in petroleum ether) to give 2-tert-butyl-4-fluoro-5-nitro-1H-indole (900 mg, 73%). 1H NMR (400 MHz, CDCl3) δ8.50 (br s, 1H), 7.86 (dd, J=7.6, 8.8 Hz, 1H), 7.13 (d, J=8.8 Hz, 1H), 6.52 (dd, J=0.4, 2.0 Hz, 1H), 1.40 (s, 9H).

후처리

  1. extractionextracted with EtOAc (100 mL×3)
  2. washThe organic layers were washed with sat. NaCl and water
  3. dry with materialdried over anhydrous Na2SO4
  4. customevaporated under vacuum
  5. customThe crude compound was purified by column chromatography on silica gel (10% EtOAc in petroleum ether)

출처 및 근거

ORD 기록
ord-ac0487345ddf4aa398b8ce4a72900742
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08623905B2

반응 노트

불러오는 중…