Isoamyl Nitrite → 3-Iodo-2-methyl-6-(trifluoromethyl)pyridine

HRID 604608ノート

反応式

HRID 604608 の反応式
N[C:2]1[C:3]([CH3:12])=[N:4][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:6][CH:7]=1.N(OCCC(C)C)=O.[I-:21]>C(Cl)(Cl)Cl>[I:21][C:2]1[C:3]([CH3:12])=[N:4][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:6][CH:7]=1

参加物

5

反応物 3

HCID 8053Isoamyl NitriteHCID 30165Iodide IonHCID 35218502-methyl-6-(trifluoromethyl)pyridin-3-amine

生成物 1

HCID 670577443-Iodo-2-methyl-6-(trifluoromethyl)pyridine

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

反応条件

温度
80 °C

実験手順

A mixture of 3-amino-2-methyl-6-(trifluoromethyl)pyridine (500 mg, 2.84 mmol), isoamyl nitrite 760 μL, 5.68 mmol) and iodide. (793 mg, 3.12 mmol) in dry CHCl3 (10 mL) was stirred at room temperature for 0.5 h. The mixture was heated at 80° C. under N2 for 4 h. The reaction mixture was quenched with saturated Na2S2O3 then partitioned between CH2Cl2 and water. The organic layer was dried (Na2SO4) and concentrated in vacuo. The residue was purified by flash chromatography (Si, 1% EtOAc in hexanes) to afford 3-iodo-2-methyl-6-(trifluoromethyl)pyridine. LCMS calc.=288.0; found=288.0 (M+1)+. 1H NMR (500 MHz, CDCl3) δ 8.25 (d, J=8.0 Hz, 1H); 7.22 (d, J=8.1 Hz, 1H); 2.83 (s, 3H).

後処理

  1. customThe reaction mixture was quenched with saturated Na2S2O3
  2. customthen partitioned between CH2Cl2 and water
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash chromatography (Si, 1% EtOAc in hexanes)

出典と根拠

ORDレコード
ord-21869445d738483aa3519101db350f49
出典データセット
uspto-grants-2011_03
特許番号
US07910592B2

反応ノート

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