Triethylamine → 2-Cyano-3-fluoropyridine

HRID 887638

反応式

HRID 887638 の反応式
[F:1][C:2]1[CH:3]=[N+:4]([O-])[CH:5]=[CH:6][CH:7]=1.C[Si]([C:13]#[N:14])(C)C.C(N(CC)CC)C>CC#N>[F:1][C:2]1[C:3]([C:13]#[N:14])=[N:4][CH:5]=[CH:6][CH:7]=1

参加物

5

反応物 3

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

生成物 1

HCID 70604082-Cyano-3-fluoropyridine

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

The mixture of 3-fluoro-pyridine 1-oxide (0.99 g, 8.75 mmol), trimethylsilyl cyanide (4.80 ml, 35.0 mmol), and triethyl amine (1.84 ml, 13.2 mmol) in 100 ml of CH3CN was heated at reflux overnight. The solvents were removed, under reduced pressure and the residue was partitioned between EtOAc and saturated NaHCO3. The organic portion was separated, dried with Na2SO4, filtered, condensed, the crude compound as purified by flash column chromatography (10 to 20% of EtOAc in hexanes). The titled compound was obtained as a light yellowish solid. MS (ES+): 123.1 (M+H)+. Calc'd for C6H3FN2—122.10.

後処理

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. customThe solvents were removed, under reduced pressure
  4. customthe residue was partitioned between EtOAc and saturated NaHCO3
  5. customThe organic portion was separated
  6. dry with materialdried with Na2SO4
  7. filtrationfiltered
  8. customcondensed
  9. customthe crude compound as purified by flash column chromatography (10 to 20% of EtOAc in hexanes)

出典と根拠

ORDレコード
ord-e568494b6bbb429ab93068d83e27aa88
出典データセット
uspto-grants-2012_08
特許番号
US08247430B2

関連ノート

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