Triethylamine → 2-Cyano-3-fluoropyridine

HRID 911312

반응식

HRID 911312 반응식
[F:1][C:2]1[CH:3]=[N+:4]([O-])[CH:5]=[CH:6][CH:7]=1.[CH2:9]([N:11](CC)CC)C.C[Si](C#N)(C)C>C(#N)C>[C:9]([C:3]1[C:2]([F:1])=[CH:7][CH:6]=[CH:5][N:4]=1)#[N:11]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 82115Trimethylsilyl cyanideHCID 123084Pyridine, 3-fluoro-, 1-oxide

생성물 1

HCID 70604082-Cyano-3-fluoropyridine수율 70.3%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

Dissolve 3-fluoropyridine-N-oxide (1.0 g, 8.687 mmol) in anhydrous acetonitrile (100 mL). Add triethylamine (1.319 g, 1.82 mL, 13.031 mmol), trimethylsilylcyanide (3.447 g, 4.63 mL, 34.749 mmol) and heat the mixture to reflux overnight. Cool to ambient temperature and concentrate in vacuo. Dissolve the residue in EtOAc and wash with saturated aqueous NaHCO3. Dry the organic layer over Na2SO4, filter, and concentrate in vacuo. Purify by chromatography on silica gel eluting with hexane/EtOAc (1:0 and 17:3) to give the desired intermediate as a solid (746 mg, 70%). GC-MS m/z: 122 (M+).

후처리

  1. temperatureto reflux overnight
  2. concentrationconcentrate in vacuo
  3. dissolutionDissolve the residue in EtOAc
  4. washwash with saturated aqueous NaHCO3
  5. dry with materialDry the organic layer over Na2SO4
  6. filtrationfilter
  7. concentrationconcentrate in vacuo
  8. customPurify by chromatography on silica gel eluting with hexane/EtOAc (1:0 and 17:3)

출처 및 근거

ORD 기록
ord-3dd873d0c5e14629b3ff0b6ae470974e
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08022062B2

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