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

HRID 923687

반응식

HRID 923687 반응식
[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

참가 물질

4

반응물 1

HCID 215781382-Ethynyl-4,6-difluoroaniline

생성물 1

HCID 27787305,7-difluoro-1H-indole수율 85%

시약·촉매·용매 2

HCID 131734998Sodium gold(III) chloride dihydrate촉매HCID 702Ethanol용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-f11681aed86540929087e232986d94d9
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09278985B2

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