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

HRID 1403912ノート

反応式

HRID 1403912 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1118Sulfuric Acid溶媒

反応条件

温度
-10 °C

実験手順

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) δ 8.50 (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).

後処理

  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)

出典と根拠

ORDレコード
ord-779f6b23a8294977947ae4ed54ea341f
出典データセット
uspto-grants-2014_12
特許番号
US08912199B2

反応ノート

読み込み中…