2-Ethynyl-4,6-difluoroaniline → 5,7-difluoro-1H-indole

HRID 923687

反応式

HRID 923687 の反応式
[C:1]([C:3]1[CH:9]=[C:8]([F:10])[CH:7]=[C:6]([F:11])[C:4]=1[NH2:5])#[CH:2]>C(O)C.O.O.[Au](Cl)(Cl)Cl.[Na]>[F:10][C:8]1[CH:9]=[C:3]2[C:4](=[C:6]([F:11])[CH:7]=1)[NH:5][CH:2]=[CH:1]2

参加物

4

反応物 1

HCID 215781382-Ethynyl-4,6-difluoroaniline

生成物 1

HCID 27787305,7-difluoro-1H-indole収率 85%

試薬・触媒・溶媒 2

HCID 131734998Sodium gold(III) chloride dihydrate触媒HCID 702Ethanol溶媒

実験手順

The impure 2-ethynyl-4,6-difluoroaniline (4.2 g, 19 mmol) from the previous example was dissolved in ethanol (75 mL), treated with sodium gold(III) chloride dihydrate (310 mg, 0.77 mmol) and stirred for 3 h under an atmosphere of nitrogen. The mixture was concentrated, taken up in ethyl acetate, washed with water, washed with sat. NaCl, dried over sodium sulfate (Na2SO4) and evaporated. Purification by flash chromatography (SiO2, 100-200 mesh; eluting with 0-15% EtOAc in hexanes containing 2% acetic acid) provided of the title product (2.0 g, ca 85% purity): 1H NMR (400 MHz, CDCl3) δ 8.32 (s, 1H), 7.26 (dd, J=4.8, 2.0 Hz, 1H), 7.09 (dd, J=9.1, 2.2 Hz, 1H), 6.74 (ddd, J=11.2, 9.3, 2.0 Hz, 1H), 6.55 (td, J=3.3, 2.2 Hz, 1H). 19F NMR (376 MHz, CDCl3) δ −122.11, −131.96. EIMS m/z 153.

後処理

  1. concentrationThe mixture was concentrated
  2. washwashed with water
  3. washwashed with sat. NaCl
  4. dry with materialdried over sodium sulfate (Na2SO4)
  5. customevaporated
  6. customPurification
  7. washby flash chromatography (SiO2, 100-200 mesh; eluting with 0-15% EtOAc in hexanes containing 2% acetic acid)

出典と根拠

ORDレコード
ord-f11681aed86540929087e232986d94d9
出典データセット
uspto-grants-2016_03
特許番号
US09278985B2

関連ノート

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