Sodium Sulfite → 1-Acetyl-6-bromo-5-fluoro-2-methylindolin-3-one

HRID 331050ノート

反応式

HRID 331050 の反応式
C([O:4][C:5]1[C:13]2[C:8](=[CH:9][C:10]([Br:15])=[C:11]([F:14])[CH:12]=2)[N:7]([C:16](=[O:18])[CH3:17])[C:6]=1[CH3:19])(=O)C.S([O-])([O-])=O.[Na+].[Na+]>C(O)C.O>[C:16]([N:7]1[C:8]2[C:13](=[CH:12][C:11]([F:14])=[C:10]([Br:15])[CH:9]=2)[C:5](=[O:4])[CH:6]1[CH3:19])(=[O:18])[CH3:17]

参加物

5

反応物 2

HCID 24437Sodium SulfiteHCID 710904071-acetyl-6-bromo-5-fluoro-2-methyl-1H-indol-3-yl acetate

生成物 1

HCID 710896491-Acetyl-6-bromo-5-fluoro-2-methylindolin-3-one収率 72.3%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 962Water溶媒

反応条件

温度
110 °C

実験手順

To a mixture of 1-acetyl-6-bromo-5-fluoro-2-methyl-1H-indol-3-yl acetate (D87) (1.22 g, 3.72 mmol) in ethanol (15 mL) was added a solution of sodium sulfite (0.562 g, 4.46 mmol) in water (15.00 mL). The mixture was then heated at 110° C. for 2 hours. After cooling to RT, ethanol was removed under reduced pressure. The aqueous residue was poured into water (50 mL) and extracted with DCM (20 mL×3). The organic layers were combined, washed with brine (100 mL), filtered through phase separator and evaporated in vacuo. The crude residue was purified by chromatography on silica, eluting with a gradient of 0-40% ethyl acetate in cyclohexane to give title compound (769.5 mg). LCMS (A): m/z (M+H)+ 286/288, C11H9BrFNO2 requires 285/287 (acidic).

後処理

  1. temperatureAfter cooling to RT
  2. customethanol was removed under reduced pressure
  3. additionThe aqueous residue was poured into water (50 mL)
  4. extractionextracted with DCM (20 mL×3)
  5. washwashed with brine (100 mL)
  6. filtrationfiltered through phase separator
  7. customevaporated in vacuo
  8. customThe crude residue was purified by chromatography on silica
  9. washeluting with a gradient of 0-40% ethyl acetate in cyclohexane

出典と根拠

ORDレコード
ord-29ae4acd40884071af62152824cdec8b
出典データセット
uspto-grants-2014_11
特許番号
US08877742B2

反応ノート

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