1H-1,2,4-Triazole → 3-[1,2,4]Triazol-1-yl-pyridine-2-carbonitrile

HRID 857719ノート

反応式

HRID 857719 の反応式
[C:1]([C:3]1[C:8](F)=[CH:7][CH:6]=[CH:5][N:4]=1)#[N:2].C(=O)([O-])[O-].[Cs+].[Cs+].[NH:16]1[CH:20]=[N:19][CH:18]=[N:17]1>CN(C=O)C.O>[N:16]1([C:8]2[C:3]([C:1]#[N:2])=[N:4][CH:5]=[CH:6][CH:7]=2)[CH:20]=[N:19][CH:18]=[N:17]1

参加物

6

反応物 3

HCID 92571H-1,2,4-TriazoleHCID 10796Cesium carbonateHCID 70604082-Cyano-3-fluoropyridine

生成物 1

HCID 218663013-[1,2,4]Triazol-1-yl-pyridine-2-carbonitrile

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
65 °C

実験手順

To a solution of 2-cyano-3-fluoro-pyridine (2.99 g, 24.49 mmol, preparation described in case 20443, filed Jun. 4, 1999) in DMF (30 ml) is added cesium carbonate (2.03 g, 29.39 mmol) and 1,2,4-triazole (2.03 g, 29.39 mmol) and the reaction mixture is stirred at 65° C. for 4 h. After cooling to room temperature, the mixture is diluted with water and extracted with EtOAc 3 times. The aqueous layer is saturated with LiCl and further extracted with EtOAc. The combined organic layer is dried on sodium sulfate, concentrated in vacuo. The crude product is purified by flash chromatography (silica gel, 2% MeOH containing 10% NH4OH in CH2Cl2 to 6%) to give 3-[1,2,4]Triazol-1-yl-pyridine-2-carbonitrile. 1H NMR (CDCl3, 400 MHz) δ 8.95 (s, 1H); 8.8 (d, J=4 Hz, 1 H); 8.24 (s, 1H); 8.22 (d, J=8.5 Hz, 1 H); 7.75 (dd, J=4, 8.5 Hz, 1 H).

後処理

  1. temperatureAfter cooling to room temperature
  2. extractionextracted with EtOAc 3 times
  3. extractionfurther extracted with EtOAc
  4. customThe combined organic layer is dried on sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe crude product is purified by flash chromatography (silica gel, 2% MeOH containing 10% NH4OH in CH2Cl2 to 6%)

出典と根拠

ORDレコード
ord-f2e2dbc6b08e4a5c8d0bf356ec0363d6
出典データセット
uspto-grants-2006_12
特許番号
US07144899B2

反応ノート

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